My family

Monday, March 29th 2021
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I am a 39-year-old father of three wonderful daughters. My family is without question the most joyful and important thing in my life. 

Why is this relevant to Permanent Style? Two reasons. 

First, this demographic is not well-represented in the images of fashion in general, and menswear in particular. 

Fashion is largely populated by skinny boys, while classic menswear is dominated by men driving cars, smoking cigars and drinking whisky, with their arms around near-naked women. 

It’s nice to provide a small corrective to that. To talk about the deeper pleasures of being a father and bringing up children. 

There may also be an argument that this outlook on life has more in common with the ideals of Permanent Style: of buying intelligently and dressing tastefully. Flashy cars and flashy women are perhaps better suited to flashy clothing. 

The second reason it’s worth talking about my family, is that it informs why I dress as I do, and therefore the clothes we cover on PS. 

I do not live the life of an international jet-setter, and spend a good proportion of my time doing things like walking in the (currently very muddy) park, or playing with toys on my knees. 

My eldest daughters are now 13 and 10, and are often wonderfully self-sufficient. The pleasures of being with them are re-learning my British history, or introducing them to music. But my youngest is only one, and that is much more physical. 

I care enough about clothes that I want to enjoy them every day, not just when I go to town. So I want good, hard-wearing chinos as well finer worsteds. I want sweatshirts that wear in, not out. 

This why I love clothes covered on PS such as:

It’s mostly workwear, but the dressier and less costume-y end. And the best post we’ve done that represents it is probably this one, the ‘weekend capsule’

My family affect what I wear in subtler ways too. 

For example, it’s important that my wife likes what I wear. We’re never going to have exactly the same tastes, but I wear simpler, quieter things under her influence. 

She particularly favours well-fitted trousers: not tight, in fact quite the opposite of the jeggings younger men might wear, but not slouchy either - well-fitted and flattering, whether jeans or flannels. 

She also likes longer coats on me, rather than blousons and leather jackets. I think she’s right that they flatter me more, given my height, and it helps rein in my passion for suede. 

I’m realising this could become quite a long list. I’ll mention just one more, alternative point. I find it interesting why she dislikes certain things, because it’s often just down to association - reinforcing my impression that a lot of what we think about clothes is based on this. 

Belgian loafers, for example, she thinks of as posh and perhaps flash; roll necks, on the other hand, seem a little cheap, a little ‘Next’. 

This doesn’t mean I stop wearing them, and indeed I can sometimes change her mind by wearing them well myself. But it illustrates how much our impressions of clothes are just based on the other people we’ve seen wearing them. And what we think of those people.

My elder daughters have a keen sense of colour, which I find interesting. 

They’re both quite artistic, and spend a lot of time drawing, painting and creating. My eldest has her own blog about Japanese-style doodles, and they both like strongly coloured clothes.

I find that if I give them a choice between colour combinations - say, which of two ties to wear with a suit - they always have a firm opinion, and it’s usually a good one. They’ll even suggest colours or patterns to wear together. 

At their age, my brother and I would never have been able to do that. We weren’t as artistic, and we just didn’t care about clothes in the same way. He cared a little about what was cool or fashionable; I cared about wearing whatever a band wore at that moment. 

This is of course only anecdotal, and isn’t necessarily about boys vs girls. But it reinforces my belief that some people spend a lot more time thinking about clothes when they’re younger, and it helps them dress when they’re older. 

Often this is girls; often it increases when they’re older; and it’s definitely a reason a lot of men find it harder to pick out clothes.

I think it was different in previous generations as well. Both my maternal grandparents had a sense of style, but they wouldn’t have necessarily have been seen as such. 

My grandmother in particular, Jackie, always dresses in lovely combinations of blouses, cardigans and dresses. A cream blouse with a oatmeal cardigan and grey skirt, perhaps. Often very tonal; always very tasteful. 

She would say she liked clothes, if asked. But she rarely volunteers this as a topic of conversation, and sees it as quite easy and natural. It’s how she’s always dressed, and how others around her dressed when she was younger. 

My grandfather (above, far right) was much more of a dresser, and he has featured on Permanent Style in the past - specifically here and here

Pops, as he was known to us, would always be in a jacket and tie whenever we went to see him, or he came to visit us. He once said he knew it suited him best, and only more as he got older.

Yet Pops spent very little on clothes. He had nothing made, and the tie I still have, which he wore to my wedding, is polyester from Tie Rack. He liked being well-dressed, but he spent far more proportionately on food and on travel. 

My family influences hugely how I dress. The fact I have children is just as influential as whether I cycle to the office, or work in a conservative law firm. 

I think it’s worth thinking about this, and about what clothes actually suit how we live every day. It’s just as much a part of dressing well as knowing how formal shoes are, or washing your sweaters

Propriety is not just about the dress code at a wedding. It’s about being appropriately dressed in every walk of life. 

Photography: Jamie Ferguson, for Plaza Uomo and outtakes from his book, This Guy

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As thoughtful and considered as ever…and thank you Simon for yet again pointing out the value of context to dressing well. And for those of us elder gents with young(ish) families, doubly so! It’s also a satisfying pleasure to think about what to wear when the context is as everyday as a mess around in the park and on the bike with my 4 year old! Simple pleasures…


Thanks for this more personal post than informs the clothes you wear.
It resonates with me as I have a 2 year old and in a few weeks a newborn.

I also focus on “dressier workwear” clothes more (with a small child + pandemic) that can be machine washed, for example the washable chinos from Stoffa have been great in this regard.

Alfred N

Lovely. Truly we should dress well as part of living well (in the most expansive meaning of the word), and dressing has to be grounded in living.


The demographic of man with young kids is definitely under represented in menswear articles and blogs. Explaining how to dress well within the context of a family is over looked – as you say, menswear for the >30s is usually positioned as a playboy lifestyle of sports cars, weekend breaks and whiskey nights

John Jarvis

What a beautiful family! As the proud father of a 9 month old daughter, and having just started shared parental leave, I’m wondering how playing with my daughter will affect what I wear so this is interesting to see


How has your passion for clothing rubbed off on your wife over the years, Simon? Would she appreciatively note a well executed spalla camicia or drape cut? Is she herself very interested in her own clothing? Thanks as always for the great reading.


Really enjoy reading you Simon. It only makes sense to see how your daily life as a father and husband can impact your way of dressing. Would have loved to see your daughters and your wife pick up an outfit for you though!




I support this initiative!)


Good post. I note your comments on stylish workwear.One of the interesting things to me about PS over the years is that you have covered a variety of clothes.It would have been all to predictable to just concentrate on suits and odd jackets etc but you have diversified into topics such as jeans,trainers,Sagans,blousons….Style should’nt become ossified.Keep pushing at the boundaries Simon.


Yes, and you can measure it with the last suitsupply campaign ( with this subtle subtitle they dare to use ( the New normal) – is it irony, 3rd degree joke ? Real vulgarity.


Wow what a horrible campaign. The Rake too is stuck with incredibly out-dated ideas of ‘masculinity’, the one the one that Simon describes. Sadly, women’s bodies have always been used as supporting objects to sell us (men) cars, clothes, drinks, cigarettes, etc. How this is still happening in 2021, in the age of woke-ness, MeToo, hyper-activism, is really beyond me and quite saddening.


I must admit I’ve not noticed The Rake being particularly objectifying of women? Rather they are absent from it. Indeed, women are largely absent from other cigar-and-negroni-focussed-classic-menswear publications/Instagram.

I may be naive but I always assumed that part of the reason for this was that the key architects of these publications – Wei Koh, Alexander Kraft etc. were homosexual?


Neither of these men are gay, and the cigar/negroni/sports car aesthetic tends to be more of an old fashioned, ultra-masculine heterosexual ideal


James, you can skim through the Rake editorials and you will see it definitely subscribes to the ‘classic menswear’ aesthetic Simon describes at the top of this write-up.


Hi Simon, I am also 39 and have 3 children, between 2 and 8, though 2 are boys.
The casual clothes topics have always been the most relevant for me, because of more casual dresscodes at work and it eases my transition from playing on the knees with the kids to leaving the house well put together. Short, it‘s relevant for my daily life. And I don‘t need to make compromises at style, which I find exceptional helpful this times. Thanks for the insight in your life.

Dr Peter

Wonderful post! I love children and I am good with them. But I’ve never been fortunate enough to have one of my own. I do have nephews and nieces and also grand-nephews and grand-nieces. Plus an army of former college students whom I taught for years, all my surrogate children.

Being a father is such a splendid thing. Your daughters look and sound terrific. I can see how children make life so full. Thank you for this personal post.


+1 🙂


This is a lovely piece and resonates with me. I certainly started wearing sweatshirts you can wash rather than dry clean only knitwear and washing my jeans more often than every six months once I had a young family with their sticky fingers.

Peter Hall

Having a family is a huge influence. They must wash well(repeatedly) not pull out of shape, be robust enough for rolling around on the floor…and those impromptu games of cricket or painting on the table.
Fashion avoids these tricky conundrums, but we all have those ‘I’m visiting friends with kids, so want to be smart, but will end up covered in food or mud’ moments. Perhaps not a day for raw denim.

Nice article,Simon. As always.


I never really thought about the odd advertising for menswear. Perhaps they believe that men mostly only buy clothes either for work or for dating.

Perhaps an interesting article would be to ask a few tailors and RTW brands (ideally a cross section) what their distribution of customers is like and what sort of things do they usually order to get a sense of who is actually buying good quality menswear and what sort of lifestyle they have. I guess Saman Amel touch on it in their video interview (I remember them talking about flexibility in a wardrobe) but it might be interesting to see more. You could compare the answers against your readership in the next survey if you think people would answer?

Oliver Gibson

Thanks Simon, really enjoyed this post.


Cheers Simon, this post encapsulates something that’s in danger of being forgotten: we dress up not to escape to a fantasy, but to embrace living each day in a world full of real people and genuine relationships. Thank you for keeping PS so relatable.

This cup of coffee laced with cocoa and soju is the best I can do, but I raise it all the same.


Thank you. It was especially interesting reading this this (lovely) piece followed by the (moving) interview with your grandfather.


Lovely article, Simon.
With full respect for privacy, would you be comfortable sharing your eldest’s blog about Japanese doodles?

Darren McClure

This is probably one of my all time favourite posts, Simon – and i’ve been a reader for over 10yrs now. You’ve hit upon a really important point here; almost none of the marketing that is aimed at men actually reflects how we live our day-to-day lives. I’m a professional engineer, so I have a real thing for ‘function’. If things don’t work properly, or don’t work in the context they are being used, then they are not much use to us. And they are certainly not going to be good ‘value’.

Il Pennacchio


Though you don’t use the word, this is the best thing I’ve ever seen written on “lifestyle”. It’s used in an extremely vague way, but almost always aspirational, as in “I want to look like I own a yacht” or “I want to look like I spend a lot of time on private jets”. But rarely, as you do here, “This is the life I live, and this is what is best suited to it”. Well done.


Very interesting as usual, Simon. And thought-provoking as ever. I don’t have the time or spare brain-wattage to arrange those thoughts into anything coherent or even flowing but here goes.
1) Your reaction against the rather obvious, slightly naff, surely antiquated, Rake view of actual or aspirational masculinity is very worthwhile.
2) Having daughters is a very wonderful thing. I have 2.5, and am sure they have changed my whole view of the world. What are teenage boys even for?
3) But I actually do like single malt, cigars and leather armchairs. Sometimes.
4) Has practical workwear Simon met bespoke tailoring afficionado Simon? Do they have one lifestyle which their clothing matches, or two lifestyles?
5) I’m with you on the “association” idea, and its baffling manifestations in other people. It reminds me of (other) peoples’ barmy ideas about names -“you can’t call him David: they’re all one-legged bookmakers.” My partner says that rollnecks are effeminate, which I’m too puzzled by even to disagree with.
6) But she’s entirely right that the problem with men’s tailoring is that you need style as well as fit.
7) This is better than when my daughters tell me I’m wearing nonce teacher shoes. Some of their insights are valuable; some are way off. Some I’m just not sure what to think of.


Very nice post Simon. Chapeau


Hi Simon, great post. Resonating with my current thoughts, as I am 39 as well, with my first child due to arrive in late June. Funny you should mention the dislike your wife has with Belgian loafers (extendable to loafers in general or just to this particular type?) – my wife HATES loafers, mostly for poshy associations but that may be mostly relevant to our current background and city of origin. For the same reasons, she also strongly dislikes boat shoes. Maybe someday you could write an article on the most common no-gos of our beloved halves.

Tommy Mack

My wife hates loafers and deck shoes too, again for the associations mainly, not so much posh per se, I think as Louche, showy, effeminate. She told me she nearly broke up with me early on when I showed up to a date in powder-blue penny loafers and ripped jeans (fair enough really, it was an obnoxious choice back then and I certainly wouldn’t wear anything like that now!) I think anything that looks sleazy or vain on a man is off-putting to most women: unless you’re Mick Jagger, you probably can’t get away with dressing like him!


I have come around to the view that classic Sagans work best as a house shoe.They look to fragile to me to work on the street.Inside is their natural environment like the Albert slipper.My pair in dark brown look good with a pair of grey flannels.


I think shoes are the worst part of menswear for tricky associations, exemplified by loafers and boat shoes. I really like some loafers in theory but can’t actually finds a pair I like, and dislike anything I don’t actually like.
I just found a pair I might be able to get on with (Myrqvist Stenhammer) and consulted one of the daughters, who completely wrong -footed me by saying- Aren’t you a bit young for them? Grandad has a pair a bit like that and I think it’s because he can’t tie his laces any more.

Kevin Kelsey

LOVED this. Thanks for letting us see a little bit of the real you.


That’s interesting about your girls interest in color and drawing. My precious daughter was exactly the same way as a young girl and it was wonderful. This has served her well as she has grown into a vibrant and fantastic young woman. She also paid attention to my emphasis on being well dressed, but never flashy, and adopted the same approach. So, keep doing what you’re doing and the girls will emulate your approach in their own individual ways. You’re having too much fun, love it!

Valentine Hayes

We women have our notions about what “family men” should wear.


Well, would you please share these notions with us?


Please do say more Valentine


Thank you, Simon, for the personal and insightful post. Have you ever considered a post on how to dress in a way that complements your partner’s style? I must say it’s a thing I find difficult given that women’s clothes tend to be a bit flashier (and my wife’s tastes in particular).


Loved this post and I can totally relate. I have a four year old son and I noticed after he was born I quickly started getting holes in the knees of many of my jeans and chinos. I realized I spent so much time playing on the floor with my little guy that was what was causing the wear and tear on my pants. The harder working (but still smart) the better!


At the risk of sounding repetitive, great article! As a 39 yo father of two young boys, I can empathise with a lot of this. This is also a nice follow-up to your article about raw denim. Not washing jeans isn’t an option when you have a young family and nobody wants to be the conspicuously vain father in the playground who’s clearly panicking about mud and grass stains on their jeans (or sticky chocolate-covered hands on cashmere)! Clothes are great fun but if they stop you enjoying family time then I’m afraid you’ve lost perspective


As a father myself i find this a very interesting post. On a side note: chapeau for the “caffettiera” in the first photo. As an Italian i say it’s the best way to make a good coffee.


I just wanted to add another very sincere thank you for this article.

It is fun and touching. Becoming a father was an initiation to a club unlike any other. It is nice to see it come to PS, as well.

At the very least, it gave me a previously-unexplored appreciation for machine washable trousers.


Lovely post.

49 year-old with two daughters here. Strangely enough, having young children coincided with my dress becoming more formal – including my ‘at home’ wear. I think I wanted to preserve and mark-out a bit of ‘me’ rather than going down the tracksuit slobwear route that I saw in many fathers. Of course, you have charted a third way which is no doubt more practical.


Thank you for the post, Simon, from a longtime reader and admirer in a similar life stage. Great context for the clothes you cover. I find it very interesting what clothes my wife likes (OCBD, well-fitted trousers, suede chukkas) and what she will ruthlessly mock me for (Red Wings, or when I steer more towards streetwear admittedly unbecoming for my age, but also surprisingly my Barbour? Still figuring that out). Also I love the point about thinking about clothing more when one is younger, informing their style for the decades following. Sometimes it takes some time to get back to the sweetspot you were looking for all along, but with trial and error and help from places like Permanent Style it’s doable. Cheers from Los Angeles


Interesting to hear the female perspective. What does your wife think about overshirts?


Always very enjoyable to read these types of articles.

I wonder if it would be possible to have more discussion surrounding how your life and personal opinions influence the way you dress and why you’ve chosen to wear a particular piece. Personally, I find them very informative.


I really enjoy your articles as they provide a lot of information. Highlighting good brands, identifying what makes something good quality and how individual items can be worn etc. has been great, especially as a new dresser. (So apologies for the wall of text in advance.)

However, I’m also quite interested on how your own perspectives and lifestyle might influence how you dress. Why have you chosen to pair particular things together and why do you think they pair well together?
How/why were certain patterns and colours chosen in an outfit and why do you like the effect? How did your likes and dislikes over time influenced how you dress?

From reading the site, my personal questions would be:

1. When commissioning your Levi jeans, why did you decide to widen the leg opening from 17.5cm to 18cm for your next pair?

Personally, I thought the original pair looked great too. So how did your personal preference decide it was too slim for you? Was there a particular image you had in mind? Was the opening widened because of comfort or silhouette? How can these adjustments impact the overall look of an outfit?

2. At one point there was some brief commentary on you deciding to shorten your Edward Sexton overcoat.

Again, was it an issue of practicality and what change did shortening the length have on the impact of an outfit? Did the new shortened length fit just better with your day to day activities while still adhering to the original design and impact you had in mind?

3. You’ve always praised the versatility of the Valstarino, with the ability to fit smarter and more casual outfits. Since purchasing my own, I definitely have to agree and it was a great buy based on your reviews!

Compared to similar items such as the Stoffa flight jacket, why do you have such a clear preference to the former?

For the less educated, the two can fill similar roles. So again, I would be interested to know your opinions behind why, when and where you might wear one over the other. Just understanding your personal favourites over similar items would be great for those figuring out their own.

On the subject of lifestyle, as a reader it would also be interesting to get your opinions on how you incorporate or consider clothes/”smarter” items of clothing/elements of tailoring in relation to doing certain activities or being in certain environments. An expansion on “Which Office Are You”, but for other areas outside of work would be very helpful. It doesn’t have to be a rigid guide, but I think it would make for more interesting reading.

Hope this provides more information based upon my previous comment. Thanks for the great reading over the years Simon, it’s very much appreciated.


I really look forward to it, with the way you tackle things I think you have a lot to give in this area that’s often a bit neglected. So thanks for all the hard work you do!

I appreciate the continued effort to help others make more informed decisions, as well as know what to look for and consider when formulating their own tastes.

(Side note: The Bridge Coat was fantastic purchase too. Wonderfully designed and made. The latest Private White re-release is also very tasteful and I selfishly hope there’ll always be more collaborations in the future.)


Hello Simon,
Thank you for an intelligent thoughtful article.
I’d agree the age group you reference is underrepresented in marketing, however I believe this is pretty much the case across the board in menswear, outwith those aspiring to appear on tacky reality shows.
Speaking as a father, husband, grandfather of daughters and granddaughters and a son, I find some advertising is simply ‘beyond the pail’ in this space – especially in its representation of women. As for the idolatry of a ‘cigars, brandy and flashy cars’ lifestyle is at best a bit sad old fashioned stereotypical and at worst promotes acceptance of objectionable and inappropriate behaviours.
One of the ways to address this trend is to vote with our wallets! It doesn’t have to be this way.
Ok, sorry when I saw the advert and the other references, I had to get the above out of the way.
I find much of the article delightful. I too appreciate the input (and exquisite taste) of my wife of nearly 47 years, every clothing mistake I have made has been my own! Her advise is simple, does it look good on me (not just do I like it) , what will I wear it with, will I wear it and the words ‘quirky and fun’ in the context of clothing and interior design to be avoided at all costs!
One of my granddaughters is a similar age to your daughter and it’s fascinating to witness her emerging character and style.
Finally Simon, your perspective is (in my opinion) spot on.
All the best.

R Abbott

One thing I noticed is that the marketing for menswear tends to be on the flamboyant side and that as a practical matter, lot of the products that get lots of publicity are difficult for married or “coupled” men to wear. The writing is usually from a perspective of what a man of sophisticated tastes should wear if he wants to impress other men with equally sophisticated tastes. Although the product advertising tends to include a sexy women next to the man, it very rarely takes into account the tastes of actual women.

The Sagans are a classic example. They’e been featured prominently on this website and in many menswear publications and product advertisements. (A lot of advertisements these days feature men wearing suede Belgian loafers, even if they’re not Sagans). I have a pair in dark brown and quite like them, and yet, I can’t get much wear out of them because my wife can’t stand them. Like your wife, she considers them too effete. I still wear mine from time to time but won’t be buying an additional pair.

I’ve seen quite a bit of arm chair philosophizing online about shifting views on masculinity, and yet most of the women I know – who aren’t necessarily conservative at all in their politics – tend to have fairly traditional tastes when it comes to mens fashion and what they want their husbands or boyfriends to wear.

Lance Wimberly

Thanks for sharing. Important post.


This is a great post mate. While reading many of your articles, I was always reflecting how practical certain clothes gonna be. Leaving in a house, looking after the kids, spending all the leisure time around the water is hard on fine clothing. I need to be able to wash the clothes easily after my daughter uses them instead of a napkin. They have to be hard wearing but still stylish. Great article, indeed.

Lily Crompton

Hi everybody!!!!
This is lily, Simon’s daughter. I’m 13 and I’m sooooooo excited to be on his blog!!!!!!!!! If you are interested or like kawaii things here is the link to my blog:
I love to draw and paint and I want to be an illustrator when I grow up
I hope you like my blog ? don’t forget to check out the video page!!


Thank you for sharing, Lily. I loved watching your video, seeing those paint dots being turned into all kind of animals and creatures. Follow your dream, you’re good. When I was your age, there was a boy in our classroom who was painting and drawing all the time. Guess what? He’s an illustrator and graphic designer now 🙂

Lily Crompton

Wow that’s amazing!!! Hopefully one day I will be an illustrator too haha
I’m so glad you like my blog ?


Hello Lily,

Your Dad’s blog is great!

I would be delighted to certainly have a look at your Blog and if you don’t mind I will ask my 9 year old Daughter, Saanvi, to have a look and follow it?

She is also very creative and loves to draw. Right now, she is coming up with an idea for a short novel (only a few pages) which she will also illustrate, so she might really like your blog.

Many thanks.

Lily Crompton

Wow!!! Tell Saanvi I hope she likes my blog and that I’m sure her story will be great!!


Hi Lily, just to let you know she checked out your blog and really liked it. I am sure she is going to find it an inspiration!

Keep up the good work!!


Hi Lily,
Thank you for sharing your blog. It’s really impressive. My daughter is 10 years old and I am sure she will really enjoy it. She is always looking for drawing videos online. Keep up the great work.

Simon, thank you for a great article. Being a dad and being interested in clothes is a challenge at times. Really helpful to hear your insights and to fill that gap that is so forgotten by the wider market.


Hey Lily
Thanks for the link. My two boys love to draw & we will check it out. BTW, although you probably already know, you have a really cool Dad. Good luck with your art career.

Lily Crompton

Yep my dad is great ?


A superb post, Simon. I’ve certainly gained a new appreciation for loopwheeled sweatshirts over the past month as a new father: they’re comfortable, easy to care for and soft on baby skin. And, given that I’m colourblind, my wife is invaluable when it comes to choosing combinations.


Very interesting read Simon.

I am 42 and have 2 girls aged 9 and 4 (very soon). They are the apples of my eye for many reasons but one is their natural flair for clothing, colours combinations etc. Both of them pick out their own clothing when outside of school/nursery and the older one runs it by me for my opinion (as do I in reverse) when we are off out somewhere. For her last Birthday I asked her what she wanted and she said just clothes and books. Brilliant to hear for me at least.

I showed her the Donegal the other day and she loved it, even asking why more people don’t wear “things like this but lots of people wear those big black puffy jackets with black trousers or bright trainers”. There’s hope yet and I pray it lasts!

As for myself I have always loved clothes, a love supported and encouraged by the most elegant woman (My Aunt) from a young age. My wife I would say is less interested, but still dresses well so that we complement one another when out together. But, on a daily basis, even when considering the most casual informal look, I shall still think about colour, texture, layering, the weather, activities etc and really enjoy that process. Conveniently she also buys into the theory that average/cheap men’s clothing generally looks it (broad generalisation) (and therefore I buy beautiful investment pieces, where fit is paramount) but that women are genuinely able to have a wider selection of reasonably priced clothing that still looks good.

My daily activities and family do influence to a great degree what I wear but I always try to push the boundaries to end up smartening up the look, or making it more interesting and personal to me.


Hi, Simon. I’m a soon to be dad of a boy and very much appreciated this post

You don’t seem the sort of dad to directly intervene with what your kids would wear, but naturally the way parents present themselves is a major factor in terms of influencing how children dress. Do you observe any style traits that likely rubbed off on them from you and their mother? I get it if that’s somewhat an intangible nature vs nurture sort of question, especially given their age.

If you were to have a son, do you suspect the way you might influence his style would be any different? It’s not a very profound observation of mine but it’s clear that girls are typically a lot more sensitive and attuned to fashion and beauty standards than boys are, so I wouldn’t be surprised if the latter would benefit from more direction when it comes to imparting your style values upon them.

Speaking of which, what sort would you like to see in your kids as they become young adults?
I’d probably go for; Flattering yet modest and elegant yet relevant.


Tommy Mack

Hi Simon, I’m 39, same as you and have two kids (Sophie, 6 and James, 3)

I definitely agree on the propriety of the smart workwear aesthetic (though with a bit of preppy/Ivy League style mixed in as I’m a small, slightly built man so suit this look) – I can do chores, play with the kids and work (as a private tutor), looking smart and appropriate for all.

You talk about propriety a lot. It often goes unmentioned but I tend to agree it’s fundamental in dressing well. When I first quit my school teaching job to become a full-time home tutor, I thought I would continue to wear a suit & tie for work: to get myself in a professional mindset and also of course because I enjoy tailoring. I don’t think I even kept my suit on the first day! I felt a bit silly wearing a suit and tie to work from home or cycling to a student’s house. More importantly, I had to recognise that if a student engages a personal tutor, then one way or another, they aren’t getting all they need from their school education so dressing like a teacher perhaps doesn’t strike the right note.

At the other end of the scale, when I first became a dad, I found I was reflexively wearing very scruffy old clothes around my kids to “save” all my better clothes for going out etc. It took me a while to realise that, like most new parents, I wasn’t doing much going out so it was rather pointless wearing my worst clothes 90% of the time. Since then I’ve rethought much of my wardrobe to along more smart-casual lines. Form must follow function and all that!

Tommy Mack

Hi Simon

My day-to-day wardrobe isn’t a million miles from what you describe in the article but as I say, a little more preppy, which I guess is an evolution from my mod days! Private tutors seem to wear a full spectrum of styles from suits to jeans and T shirts. Key importance is for the clothes to be clean, well-maintained and fitted, well-chosen and not loud (like most day-to-day situations really)

I generally don’t have time to change clothes between work and child-bearing/household chores so I tend to go for knitwear over button-down shirts with cords or fitted jeans in the winter (the occasional pair of “proper” worsted/flannel slacks more for variation than necessity) and polo shirts or s/s linen shirts with chinos in the summer plus a pair of Toms mule slippers in a herringbone faux-tweed round the house (I have very mild psoriatic arthritis in my joints so I’ve been advised to wear something cushioned) I don’t like sportswear or what I’d call silly fashion jeans (ripped, distressed, engineered, daft cuts) so my work clothes are pretty much what I’d choose to wear anyway.

Tommy Mack

On the subject of children developing their own sense of style, I’m always impressed how well my 6 year-old can coordinate outfits given how garish most of her clothes are! That old cliché about women having a better sense of colour (which is in fact rooted in solid science, females typically having more variation in the cone cells of the retina and so usually better able to distinguish between similar hues)

Even our three year-old tends to know what he wants to wear (he had a phase where he would only wear plain T-shirts, not patterns or characters!) Although he does like (ugh) Crocs, something I’m hoping won’t last!


I am a proud father of three great children the youngest is now close to finishing her first year in university. So dressing for rough and tumble are behind me. Simon, your final sentence really resonated “Propriety….It’s about being appropriately dressed in every walk of life”. Again I hope in the post Covid19 era where the bar has been lowered so low that what I view as being appropriately dressed ( a suit and tie at work) is not judged to be looking like a dinosaur….


Excellent thoughtful article. Clothing at the bottom line is an expression of self. I think too much emphasis is given to the concept of clothing as symbolic power, status and social standing. Being a father, and now grandfather, of particularly small robust children requires solid practicable wear, being a man for all seasons as you engage with your children. Too many people think/believe that style and taste are only components of a wardrobe these days.


I enjoy reading your blog in general, but this post was great. Assembling a wardrobe for one’s actual life is an important consideration, and not doing so is the main reason for having “nothing to wear”.


Oh, Lily. Shameless advertising! ? Good luck with the venture!

Simon – I agree with all of this. Context is everything and having a very young child, you will understand the absolute fear of the “dry clean only” label. Do enjoy these years – they go so quickly – and good luck with the mid-teenage years ……

michael powell

Well done, Simon! Well done!


A very thoughtful and interesting article enlivened by the wealth of comment – thanks Simon and everyone.

I have just a few comments – the first in defence of my peers in marketing, not all whiskey, car or menswear adverts are sexist or based on a power dynamic, most of us have willingly adopted the zeitgeist as a true expression of how the populace wants to live life today and we’re not going to influence how they see the brands we represent if we go against that too far or too often.

More significantly for me, as a father of two girls now in their early 30’s is how the article and the comments resonate with my recollection of that period in their growing up and how the foundations with regard to dress (neat, tidy, conservative – not flashy but individual) laid down then have carried through and are recognisable in how the girls present themselves in work and personal life today. The styling queues we set for ourselves we pass on to our children, in the clothes we buy for them and in the image they build up from their parents and their parents friends. How they dress at school and in their teenage years, when its not about fitting in, is all about statement making – be that positive or negative how we as parents react goes on to influence their choices in years to come; clothes as personal expression matter.

I was amused, having read the blog in the morning, to find my wife thinning our massive collection of family photographs later in the afternoon. With the ‘keepers’ carefully collated by year and event my sartorial pathway was spread out in front of me – deteriorating steadily as child rearing absorbed more and more of the monthly income and puddle jumping and beach scrambling had the expected impact, splitting very firmly into work clothes and stuff to keep the cold at bay then returning to civilisation – marked in the photographs by the emergence of three distinct ‘looks’ – the work look, the family at home look (not quite as battered as before) and a look that would eventually pass muster with my girls as OK to be seen with (I was never a trendy dad).

Sebastián P

Thanks for this much needed article, Simon. It is indeed a shame how tailoring is normally advertised in the industry, so it is very refreshing to have a break from that. It is also quite unnerving when you happen to enjoy both drinks and cigars but not all of those cultural associations of the pseudo-James Bond type.

Your article made me realise something. When I started reading your blog, I did so because I was interested in tailoring. But the more I have learned about clothes and dressing, the less interested I have become in tailoring. Don’t get me wrong-I still enjoy it a lot. But there is no point in focusing only on that side of menswear when, realistically, my lifestyle and environment give me relatively few opportunities to wear a suit.

Sebastián P

It is being addressed, for the most part. Even though I mentioned that regarding suits, I have started finding value and beauty in things that I would have considered dull or too irrelevant before, like a simple pair of jeans. I have also found your guides on capsule wardrobes quite useful as well, being a postgraduate with a limited budget myself. Thanks for that.


Speaking of T-Shirts, which other brands you would recommend?
Although I love their drape, most brands that make them tend to choose a rather boxy, non-slim fit which is not the most flattering for slimmer bodies without big arms.

Anyway, really enjoyed reading you!


Sounds like another PS shop special


Tom & Simon,
I bought a circular knitted tee today whilst out clothes shopping here in Hong Kong from Japanese brand Studio D’artisan.
In terms of fit, it’s noticeably different to others i’ve tried and own – tighter across the chest, slimmer through the body, higher arm holes and a touch longer. I sized up 2 sizes to XL and it’s still quite fitted.
I’ve got tees from Allevol, Toys McCoy, The Flat Head and Pherrow’s also and I tried a one from Warehouse (Lot 4601) today as well and the Studio D’Artisan is the slimmest of the bunch and probably the heaviest as well.
The Toys McCoy tees are similar, (I size up to XL) quite fitted across the chest but to a lesser degree. There are noticeably of lower quality though but much cheaper.
I buy my Japanese tees at Take5 – The Flat Head, Warehouse and Studio D’artisan $650, Toy’s McCoy $380.
Hope it helps.


Try Son of a Tailor
I have bought all their bespoke Ts…excellent quality


Thanks Simon
Good post. I am going to have a pair of linen trousers (w/ cuffs) made for the summer for general about town behavior. Will wear with both casual suede loafers and doek court shoes (I know not to your taste but I like that high/low dressing). What color would you most recommend? I already have an olive pair and probably don’t want cream. Sorry – a bit tangential to this post!


Thanks, any Brisbane Moss you think might look alright? Maybe their “natural”. Otherwise not a dark brown?


As everyone else has said Simon, this is am excellent article.
I’m hoping to see more along these lines, particularly as I’m trying to find more well considered casual elements to add to my style and you remain one of my key style inspirations.


A post of parent-friendly dressing would be very much appreciated!

On a practical note, what shoes do you wear to the muddy park? Out of fear of having my nice shoes trashed, I’ve taken to wearing running shoes. This means I’ve become the guy I look at and roll my eyes…


I also have a thing for suede and slightly longer outerwear suits me also better (I think it stretches a bit at my 5 -10 height). I am lucky therefore to have a suede jacket that is maybe just as long as the PS Wax Walker. It is a peace with character. Similar in style to a safari jacket. Beaten up and well lived in. It was already drenched in rain during a severe rain in Rome during my last holidays before Covid. The jacket was handed down to me from my uncle ten years ago. Nobody knows who made it. No labels. Bought many years ago at a night out from an elegant nice stranger in exchange for the financing of a taxi ride. This is going to stay as a family heritage peace, if I can. Just have to convince my daughter.


Thanks for your article, Simon.I am 58 and father of two boys…men now. But their choice of cloths were completely different to mine and used to make fun of my choice of clothing…I always use to tell them ”the more you try not to dress like me the more you will when you grow up”. They appreciate it now.


Would be interested in you doing an interview with Lulu Lytle given her work to support craft, having bought out the UKs only rattan weaver.

Valentine Hayes

My best advice is to dress to look like you have self pride!


I have always enjoyed the “casual Simon” and it’s actually very nice to see you apply the same care and consideration in your outfits. Speaking of more casual clothing, can I ask you which brands would you recommend for a RTW overshirt?


A really enjoyable article, Simon, thank you for sharing. I notice you’re wearing the GMT in your outfits more and more and I wonder if it’s a detail that in some ways captures where your whole style is at the moment – robust, practical, informal, elegant, classic, understated?


Well I absolutely concur with all the other positive comments; this was a lovely read and provides some delightful context to the blog, your style, and the practicalities of a considered wardrobe. The only thing I would say is I had assumed you were quite a bit older ? And mainly because 39 seems young to have such an extensive and expensive wardrobe! For how long has PS been running now?


Hi Simon,
Thanks for sharing this side of your life experience.
From your oldest daughter, I still have this first pic in my mind.
This post sheds a different light on your passion and how your family is anyhow also involved in your journey.
“Nothing great in the world has ever been accomplished without passion”. G.W.F. Hegel.


Great, Simon!!!

Edward Scott-Bleming

Although I have have never cared for, nor will ever have, a wife and kids of any sort I actually very much appreciate the writing here Simon.

It’s a humanising piece that gives us all a real insight to the ‘man behind the blog’; I’ve read elsewhere that you’re considered a snob but this evidently these people know nothing.

Somewhat ironically, I probably fit the ‘flashy’ category of market you speak of more than I’d care to admit (as a confirmed bachelor I love both cars and women who look good!) but I don’t really go for flashy clothes; as a reader of your blog for at least 6-7 years now, you have certainly informed and influenced my choice of dress for the better.


Your wife’s ideas on male dress are interesting.Personally,I think that fine roll necks in light colours like white or sky blue might be considered flashy or effete but darker colours such as navy or charcoal whether in fine or chunky knits are more manly.Your thoughts?
Speaking tangentially one should respect other people’s views on clothes but be sometimes wary of adopting them.My own experience tells me to stick to my own taste rather than always being enthralled by others.My tailors in the past and close females have sometimes made suggestions that were way off the mark.It’s a difficult balancing act trying to work out who to listen to,yourself or other people.

Michael Ryan

Thanks Simon, an interesting read, especially for me. I ‘m 55 with three daughters and they and my wife do have an influence on how I dress to a certain extent. Though my wife’s dislike of anything red or bungundy on me doesn’t mean I don’t own anything that colour, I just don’t wear them on nights out together. Though you probably already know – I’d watch out when that one year old becomes a toddler. It took months to figure out the mysterious and varied stains on my pants were coming from little sticky fingers holding on to my trousers in the morning.


Hi wonderful article as usual. I’m mid fifties with 3 boys 2 at university and 1 at boarding school. Interesting dynamic as they are more streetwear fellows and think their old man a bit odd of being so particular about his clothes. But they grudgingly admit I’m well dressed for my age (buggers!). I overheard one of their friends saying your dad looks like James Bond so I think I got some cred there but they are still some way from asking dad for clothing advice. It’s a different world for them but hope springs eternal that they will come around. Kids!


Hi Simon,

as a father of 4, soon 5 I recognize myself completely in this article and thank you for having written it. After all, the essential is there, and as important as it is, the sartorial world is only very secondary compared to the duty of transmission that we have. It’s interesting to see how we can, no doubt indirectly, awaken our children to beauty through clothing. Like you, I have memories of my father and my grandfathers who were always very well dressed, probably not bespoke, but always with great dignity, and this has shaped my approach to clothing.Even now, my father, with his tweed jackets, shetland jumpers and paraboots would not look out of place in a Drake’s ad.
Anyway, thank you for this article, very personal and which speaks to me a lot!

George Blumfield

Good post, although I live in an area where summer temperatures climb to 115 degrees F, so clothes are lighter in weight. I favor Dickies 874 workwear for everyday and Wrangler cowboy cut jeans over overpriced Levis. PS I’m a little older than yourself @ 88years. Still looking for a reasonable priced double breasted blazer in box style, straight down, size 50, 4-1/4″ lapels. Best wishes to you and your family.


Wonderful article. Love the lived-in look and feel of your attire as well its flexibility for the dad life. Also appreciate the push back on the more toxic elements that sometimes menswear exhibits or showcases. As a ‘girl dad’ myself, I’ve become more acutely aware that the imagery around menswear isn’t always healthy. Kudos for addressing this and mentioning the strong influences you have from the women in your life as well.

Paul C.

Hi Simon. As a long time reader nearing his thirties this post together with the weekend capsule are very helpful. In business and the professions it is easier to get clothes right by staying on the conservative side, with your website and its commenters essential help when playing with the boundaries. Leisure and WFH clothes are more risk prone – the comment below on jeans and trainers for muddy parks is spot on. Like many readers I expect the next decade to be less formal most of the week due to office downsizing and also filled with my friend’s and sister’s children. Very keen for more inspiration from you to avoid the preening bachelor and suburban dad (without the valid excuse of being one) looks! Also, in high school I wore my mother’s illustrations as pins on military field jackets and thought your daughter’s season doodles would be lovely too. Well done there Lily!

Nate Rose

Simon – This was a wonderful read. I’m in my early 30s and have two children under 3. My interest in your website mostly coincides with the birth of my son and also a new job that initially had a dress code.

One of the pleasures I’ve found in clothing, in a similar vein to working in raw denim, is how clothing can come to fit one and deliver a sense of intentionality. For example, I’ve ditched expensive t-shirts as they are ripe for being wrecked by toddlers and baby spit-up on the shoulder. This actually puts a smile on my face because I then know the utility of what I am wearing or buying. With that being said, if you have any tips for removing greasy, pizza-finger stains, I’ll gladly take them.

Floyd Shelton

Doesn’t a gentleman always walk on the outside?


Hey Simon, nice tender way to place your taste in clothes in a very relatable family context. Can you play ‘Agony Uncle’ for me here: made a new female friend over lockdown and she can’t wait to finally meet me this summer if it no longer is a crime to travel. But there is a fly in the ointment, I have a feeling she cannot comprehend how much well made clothes for men costs. She has even suggested €10 blazers, and won’t stop saying you really don’t need to break the bank to dress well. I have however resisted her promptings, explaining that good clothes are made by artisans who deserve our support. I recently sent her photos of loafers from Edward Green which said she did not fancy. I would don them in a heartbeat. I really suspect she doesn’t get it, and there may be trouble ahead! Please what shall I do? PS readers, please feel free to advise me.


I had a similar conversation with a friend of mine about a nearly 1000£ motorcycle jacket. However once we found out that he buys 150£ jackets once a year, but my jacket had a 5 year warranty, argument died down quite quickly.
My current girlfriend stopped complaining too much when shown a 7 year old jacket that after dropping couple pounds, fixing some lining and swapping out buttons I could wear 7 more years, and having more than decade old polo shirt that still looks ok worn shopping.

But that aside, if she is a friend, you don’t have to agree on everything. Part of friendship is agreeing to disagree on certain things..

If she is more than a friend, again, as long as your clothes budget doesn’t come at the expense of anything else that’s meaningful… agree to disagree! Everyone has a thing they spend more money than they should. For us it happens to be clothes and shoes, for some people cars, for some, watches, for some, parties, alcohol and smoking…


Just wanted to say great post I too am 39 with twin three year old girls and this resonated so well with my experience. I’ve been reading your posts for years now from Seattle and always appreciated your sense of style and the clothes you have profiled. So true how my style has changed since having kids and needing clothes that I can wear in!

R Abbott

Simon, I’d be curious how you (or some of your readers) are dealing with the wardrobe overflow and uncertainty caused by the pandemic. Prior to the pandemic, I dressed for the office 5 days a week (mainly sports coat but sometimes suits), and I also war sports coats for church, for nice dinners out, etc. So approximately 80% of my wardrobe was tailored or relatively dressy. But with COVID and working from home, I suddenly found that all that worsted material and dress shirts were of little use, so I developed a new wardrobe with oxford shirts supplanting dress shirts, cords and chinos supplanting dress trousers, etc. I also bought more flannel (which can go either way in terms of formality) and more knitwear. It’s a different world.

Here in the US, restrictions are slackening and the dinners are going back, and I’ve started going back to the office once a week but at this point, it seems unlikely that I’ll ever be going to the office on a daily basis again. (I bill clients on an hourly basis, so it doesn’t make sense to lose 8-10 hours a week commuting).

So now I’m left with a mammoth wardrobe that needs to be downsized but I’m loathe to get rid of perfectly fine clothing when there is at least a possibility that if circumstances change enough I’ll be able to use it again – if not as often as before.

For now, I’ve found your posts about workwear and more casual clothing especially useful, not only because I’m working from home, but because I have two young children. The youngest is almost 3 and incredibly messy (and has a nasty habit of getting his mess on everything and everyone) so I try to avoid wearing anything too delicate around the house! I also change more often than I used to. I might wear a cashmere sweater when I’m working, then change into a tougher wool sweater for a coffee break or lunch when I anticipate interactions with the children, and then change back to the softer cashmere when I return to my home office. My wife likes to tease me about all these changes, but then again, she’s not as particular about clothing as I am!

Jeremy Harris

Wow! I just stumbled upon your site and I feel as if I have landed. I am 45 and I have two young daughters. I have spent a significant portion of my life working in fashion but never found a home it, the reason why I changed my career focus. I love looking and feeling good in my every day wear. I look forward to reading from here on out.
BTW How to I purchase the Gieves and Hawks bespoke pea coat?


Hi Simon
Perhaps my favourite piece of yours to date. Whilst naturally it’s a clothing focussed article – it’s great to read a touch more about your day to day existence and how everything plays a part. Not expecting an autobiography by any means (and a right to privacy always respected!) – but I’m sure like many other regular readers it’s always lovely to see what goes on behind the threads. Thanks for sharing.

Thomas Mastronardi

Amen, my friend.


Hi Simon,

I love this post – very grounded in reality. Thank you!

I have a potentially very silly question: how did having a newborn change the day-to-day practicalities of dressing well, be it casual or tailored? I have a three-week old now and find my attention to what I wear around the house (and personal hygiene generally) initially being the subject of compromise and then outright surrender to the slovenly side. Even dressing up for work in the mornings in jacket and tie I could be called upon at any time to change a nappy, clean up resurrected milk, etc..

Henrik Hjerl

An interesting take – brilliant!


Recently I decided to take on more physical hobbies, working with wood, metal, vehicles. Around the house I like to be able to switch context and catch-up on my projects any little bits of time that become available. This drastically changed what I wear around the house…for now. The good thing Is I essentially just wear the older jumpers, trousers with holes or stained, etc that I had at the back of the closet. So I’m still getting use out of my clothes, just they have more grease and holes in them now.


Hi Simon, I have just returned to this article having (unexpectedly) found out I am going to become a father for the second time after a rather long gap. It really adds a lovely personal touch to have these articles spread out amongst the others on this site. I’m sure their alway popular with readers. Whilst I’m always tempted by fine clothes my general inclination is for tougher washable clothes, generally cotton. Or for tailoring, the more hardy fabrics such as tweed. I have found these most practical in my day to day life regardless of having children or not. I do not have to dress formally for work so I find I dress up more outside of work rather than for it. Could I ask how you have found the adjustment to having a very young child again after what I hope you don’t mind me saying is a rather long time after the last one?


Good article..I can relate….I have a daughter who I just walked down the aisle on august 15, 2021..great joy…i remember when she gave me a father’s day in which she wrote at the bottom “daddy whenever I need you you are always there..Simon that is our job..peace

Christopher Grate

Thank you for writing this Simon, its great to understand your lifestyle and why you dress the way you do. Though I don’t have children, we share very similar aesthetics and you’ve really helped me own my taste and not be afraid to stick to it. Personally, I dress the way the way I dress because I have always preferred understated style, the ease of making tailoring look effortless as if one’s clothes are simply an extension of them, not agnostic to their physical being. As I approach 37, I’m challenging my style in different ways like making it a point to build a suitable shoe wardrobe so sneakers are not my grab and go casual choice and working with a tailor to break certain mental barriers of style rules because of my large stature. Sorry, long comment-basically just wanted to say thank you, words can’t express how much you’ve helped me along my journey.