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In our recent article 'Outfits that I got wrong', a reader commented that he would be interested in the opposite post. Not outfits I got right - hopefully there are lots of those - but ones I got the most right, or I like the most. Perhaps, those that define me the most.

I think those criteria all go together. The outfits that I really like are also the ones that feel the most personal, and that I am most comfortable in. 

There are lots of very sharp, dressed-up looks that I love as well, but they tend to be more specific to particular events (eg Pitti) or circumstances, and not everyday looks.

The thing that gives me the most pleasure, in other words, is what I've always espoused: simply being well-dressed. 

The outfit above is a good example. Taken as part of the campaign shoot for the first launch of our Bridge Coat, it features a dark roll neck under the coat, with dark-green flannel trousers and brown-suede boots. 

I guess green flannel is quite unusual, but it’s so dark that few people would notice the colour - they just look like dark wool trousers. What’s more striking is the simplicity of the whole, and the emphasis on cut and proportion. 

I’m carrying a tan-leather doctor’s bag, which is pretty striking and luxurious. But there’s no reason I couldn’t just have a simple tote, or no bag at all. 

And the same goes for the tobacco-coloured suede cap. The colour is beautiful with the rich navy of the Bridge Coat. But it also stands out, and without it everything is much simpler and subtler. A grey or cream watch cap would be almost anonymous.

So a look that I love for its impact and versatility - that can be photoshoot-worthy or very everyday. 

Another thing these outfits have in common is that they’ve been frequently referenced by readers - on the website, on email, and in consultancy sessions. 

I think the reason is that most readers have the same aim of looking simply well dressed. They might follow more unusual dressers on Instagram, and find what they wear interesting, but most of the time they just want to have good clothes they can put on every day, and look good, without having to think about it too much. 

The outfit above is a perfect example of that. It’s essentially just a suede jacket with a blue oxford shirt and jeans. There’s nothing loud about it, or that would make you do a double-take if you saw it on the street. 

But there’s so much more going on. The jacket has a lovely colour and heft, being reverse horsehide, and there is the vintage detail of the rounded collar. The jeans are beautifully worn in - vintage, but they could just as easily be a very loved personal pair. 

And the shirt is made in the PS Oxford fabric, with its old-fashioned slubbiness and washed-in comfort. Plus it’s cut with a collar that stands up and frames the face. 

I want to go and wear that outfit again tomorrow now. It feels so me, and every item in it makes me happy.

The next outfit is much more dressed up, yet has many principles in common with the two above. 

It’s my grey-flannel suit from Panico, worn with a lilac shadow-stripe shirt and grey knitted tie. Over the top is a Cifonelli overcoat in dark-brown Tengri yak cloth

It’s smart but subtle. There is a lovely feeling to being dressed up and buttoned down like this, with a good tie cinched into the neck, and everything from shirt to jacket to coat cut to function together. I love doing it whenever I can. 

But the combination isn’t showy, as it’s all dark, muted and textured. There are no bright colours, no windowpane checks or tie pins. Yet it’s unusual too. You’re unlikely to find many people wearing a tonal suit and tie, with a lilac stripe underneath. 

And this gives it character. Simple, subtle things can often be boring; but they don’t have to be. This isn’t, and I don’t think any of those outfits are really. It's that character that makes them feel very personal, very me. 

Outfit number four is more casual, but continues all these themes. 

Yes, it’s just jeans, a grey sweater, a raglan coat and a cap. But the white jeans are a little unusual, as is the combination of smart shoes, coat and shirt, with a baseball cap. 

The colour palette gives it personality. It’s mostly neutrals, with the coloured elements dark and cold. Which as above makes it personal too. 

Best of all, it passes what I call the bus-stop test. Basically, I can wear this wandering around Mayfair, but also not feel self-conscious standing at the bus stop in East Dulwich. 

The last outfit passes that test too I think, even though I might remove the pocket square.

It fulfils all the common criteria: subtle not showy, everyday yet characterful. It has something to say but it is not shouting.

It's a tailored jacket (from Eduardo de Simone) and trousers (from Whitcomb & Shaftesbury), but doesn't look anything like business/corporate clothing. This is down to the soft brown cashmere of the jacket, the cream underneath rather than white, and the suede loafers.

The character comes from it being collared knitwear, rather than a shirt, and black suede rather than more conventional brown.

Interestingly, most of these outfits are from the past three years, which I think indicates I'm improving, which is nice if true.

These and all the other outfits can be seen on the Lookbook, together with links to the articles they came from - which include details on all the clothes.

Below, I've added five more outfits that could easily have made it into this list. Making a Top 10 overall I guess.

Thank you to the readers that suggested this post - I found it interesting and useful in thinking about what I enjoy in clothes, and in style.

Photography: Jamie Ferguson, Alex Natt and Clutch Cafe


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Anonymous

Like your choices Simon.
The photo at the top of the article is over saturated… with a red bloom.

Evatt

Hi Simon,

There’s an image if you from a while back that I can’t find now but which blew me away when I saw it. You were wearing a tailored jacket and silk scarf with a watch cap on your head. The high/low, delicate/rugged mix epitomised everything that is great about your style and this website IMHO.

Anonymous

I think there’s a photo of you in that outfit here:https://www.permanentstyle.com/2019/12/ps-watch-caps-back-in-stock.html

Hermes scarf and tweed. Personally I love the de Simone outfit! Such a lovely colour of the jacket.

Fatih

Lovely outfit indeed. Is that Bryceland’s roll neck comfortable or rather scratchy at the neck given the fact that it’s not cashmere?

And man, that Cifonelly coat is one of the most beautiful coats I ever seen.

Benedikt

Good Morning Simon, great post and very inspiring. Looking well dressed but not showy is what most readers aim for I think. One question, the cream polo, is it the Dartmoor you mentioned a few weeks back? Thank you!

Benedikt

This would have been my follow up question, great news, can’t wait!

Peter

What shoes did you wear with the suede jacket outfit Simon?

Matt H

That bridge coat outfit is definitely one of my favourites, and represents how I dress myself in winter.
Another favourite of mine is the outfit with the Caliendo jacket, worn at the MTBA in 2012. A classic smart summer look.

Matt H

I rather like low contrast outfits, with any contrast coming perhaps from the tie, as in this case. I don’t know what shoes you wore, but personally I would have gone with black, or certainly only a darker brown, to ‘bookend’ the outfit.
I wasn’t really considering the glasses as I don’t wear them and am normally picturing myself in the outfit. I can see how they might work better as sunglasses.
I agree too about the pocket square. But my taste in those is rather limited.

Robin

Can’t believe you didn’t put in the tweed and jeans look .
https://www.permanentstyle.com/2014/11/harris-tweed-jacket-and-jeans.html

Surprised at how long I’ve been reading your blog but the fact that I remember it means it definitely made a impression.

I always felt you should sell that particular tweed colour in your shop.

Hugh

Speaking for myself, I find that outfit so appealing, because it feels like something I could pull off or riff on at a variety of quality levels, It has color and textural richness and contrast without pattern, and it passes your bus stop test

Dante

Definitely agree that was a good one, and I think this similar tweed is worth mentioning too:
https://www.permanentstyle.com/2019/02/strong-colour-in-accessories.html
I don’t think I could personally ever pull off a big bright orange scarf, but it’s the perfect shade to bring out all the flecks in the Donegal.
Happy to hear the Harris one is coming back!

Johannes P

I also loved that outfit very much, actually so much that I hunted down the cloth (or at least a very, very similar one) on the Internet and had a sports jacket made in it by PrologueHK. The one I finally found (after a lot of digging) was YC140 from Harris Tweed Hebrides. I do believe they said it was the last or second to last length of it that I got, but maybe you can ask them about it if you’d like.

(and it will be very interesting to see the cloth that you’re bringing back Simon and how it compares to the one I found)

Kenny

IMHO, denim jeans and baseball caps maker tweed jackets and coats (number four) look a bit scruffy. The white jeans in numbers four and nine would have been a much better choice even in damp weather. With that tweed jacket, I would have chosen cords or moleskins in tan, khaki or navy.

Baseball caps, especially with hideous logos, are often worn by those who are trying too hard to look younger than they really are. They should not be worn by mature men, especially with tailoring. Flat or baker boy caps look great with tweed but I’d wear a felt trilby or fedora with Simon’s coat.

Personally, I think that Simon much looks more stylish in his tailoring from Davide Taub, Edward Sexton, Chittleborough & Morgan and Michael Browne. Savile Row beats Naples every time!

Kenny

Simon, I honestly think that your body shape is more suited to the structure of those firms. That style is where my tastes used to lie as I’m no longer slim and trim like you (but the sloping shoulders remain!). Even in an office, I now appear to be over-dressed in a SB jacket and flannels. It’s amazing how many staff think that’s fine to turn up in t-shirts and scruffy jeans!

I loved the heady and bohemian days in the City when sharp DB suits with colourful shirts and ties were everywhere. Those who could not afford bespoke bought RTW from the likes of Ede & Ravenscroft, Hackett and New & Lingwood. I was back in the City just before Lockdown 1.0 was utterly appalled by the dreadfully low sartorial standards.

Over the last couple of decades, London has been ruined by the dumbed down culture of globalisation. Huge conglomerates and corporate raiders have ruined or destroyed many great brands. Post lockdown, we need to campaign for a return to flamboyant style and quality tailoring. Those firms in and around Savile Row will need our robust support (especially online) to survive. Rant over! 🙁

Misbah

Simon
Some great ensemble outfits you are sporting, useful for inspiration.
I sometimes wonder if these outfits will necessarily suit a younger man? This is not a criticism but can a fairly conservative outfit age a fellow?
Would welcome your views.

Dante

Maybe an odd question, but in light of the idea of having some more womenswear input, but I’d love to hear a dialogue between yourself and someone qualified about how the PS ethos can best translate to younger guys, maybe starting their careers — while being mindful of social surroundings and not trying to act above their age. For myself, I find guys like Francis Paley and Aleks Cvetkovic to be helpful, but even some of their casual stuff would make someone stand out like a sore thumb where I live.

Henry

I can only agree with Dante, I would similarly love to see something written on how to dress well as a young adult. I haven’t quite entered the workforce yet but I do enjoy incorporating more classical elements into my styling. Would love to know how to look smart and well dressed without trying to come off as dandyish or a snob.

Dante

That would be great if there’s room for it in the future. It can be tough (especially in more casual cities) to balance the “young professional” vibe with not going overboard and looking too “mature” (be it with suits or shoes or even certain fabrics/cuts. At the end of the day, I feel it’s important to make sure to show social self awareness when dressing, even if you want to turn it up a notch or stick out a bit. Part of what I love about PS is how you illustrate so many subtle ways to do that, but of course for people in their 20s dressing is a whole different world (even without throwing the fashion scene into the mix), so anyone who has similar ideas for a different generation of social conventions would be welcome.
I’m not sure if you’ve taken a look at any social commentary writings about “relaxed” dress codes (e.g. Goldman-Sachs/Silicon Valley/Zoom) but a lot of them talk about how the idea of enforcing a dress code is still present in many ways, but now with casual clothing instead of business. It’s definitely something I’ve observed on the west coast of Canada, I’m sure London has seen it as well to an extent.

Josh

Michael, Dante – and Simon, I hope you won‘t mind the recommendation for another blog! – I recently discovered, via a recommendation from another commenter here, Ethan M Wong‘s ‘streetxsprezza‘ blog, and it’s an excellent source of inspiration for twenty-something dressing with a classic edge. He definitely takes it in a distinctly LA direction, and with a strong vintage inspiration, but I personally can’t get enough of it, and it’s amazing how much of it has bled into or else been partially fed by wider trends in fashion – which, for younger dressers, is really no bad thing at all. (Berg & Berg and Scott Fraser Collection are both great brands for a younger audience too.)

I actually think there is a danger in committing to some of the safer ‘basics’ too soon; they can look rather too plain and too safe when you’re younger. Understated quality, to the detriment of expression and personal style, and no matter how luxurious, can be ageing. Better to make a few mistakes first to figure out what really works for you and whether it might stick around in your wardrobe for several years.

Josh

Scratch ‘Michael’, sorry, Misbah and Henry!

JJ Katz

Interesting article and interesting choices.
I’ve always found your more formal and structured outfits best (and worthiest of commentary).
I recognise that the majority of outfits you show here would be more psychologically comfortable for the average dude to wear in typical social settings, but who wants to look like the average dude? I also recognise that the outfits are put together with a lot more thought and quality than the average person puts into it but I can’t escape the feeling that the overall effect of a decent jacket-and-tie outfit surpasses even the most esoteric jeans-and-jumper outfit.

Peter Hall

One of the benefits of exposure to PS is my increased use of colour, especially, in shirting. Lilac,pinks and yellows are regular.

If I could pick your brains? Keen to introduce green into my wardrobe. I’m comfortable with mixing with a black pea coat. For trousers, would you say a dark green wool(or flannel, as above) is the most versatile? Is it a good match with darker shades of brown ?

Richard W

I cannot find the article but there is one where you are photographed in James Smith & Sons Umbrellas in a beautiful grey DB (A&S?). It was some time ago but has stayed with me an a fantastic example of the elegance that can be achieved with a simple outfit

Andras

Hello Simon, nice article as usually, green trousers and navy top my all the time favourite, not just here, but in many other your outfits. Mink and black Belgravias are also amazing. I’m considering that loafer as well, seen it in expressing suede, and my question which one will be nicer and more versatile in case if I plan to purchase black version as well. Thanks

Andras

Thanks Simon, I mean to purchase black and brown, but in case of brown there is two options, one is mink suede and another is espresso brown, so which one is nicer and more versatile, with black in collection as well.

Hristo (STEMESO Socks)

Interesting choices. Everything tends to be on the more casual and more quiet side.
My favourite piece of yours is your A&S jacket from the DOUBLE-BREASTED CHECKS, AND CREAM TROUSERS article.

Scott

That Panico grey flannel outfit is simply outstanding in its beauty and simplicity. There are lots of lessons to learn here. Being simply well dressed is the most important one.

Evatt

It was from your visit to the Hermes factory in March 19. Printed silk scarf, tweed jacket, grey woolen hat. Best combination ever!

Paul

Hi Simon,
Great article, thank you. It’s funny you talk about the ‘bus stop’ test. I employ what I call the ‘school run’ test i.e. if I’m not comfortable wearing an item of clothing on the school run then it’s hard to justify owning it!
I really like the fact that you’ve explored your emotional response to clothing within this article. I imagine that for many of us it’s hard to justify spending such large amounts of money on clothing. However the pleasure and happiness we derive from these clothes certainly helps!

Kevin

The Caraceni jacket is my favorite. I’m glad it made it into the top ten.

For anyone wanting to read more, here’s the quick way to get there: https://www.permanentstyle.com/2018/07/double-breasted-cotton-jacket-and-striped-shirt.html

The picture you included above is probably my favorite on the entire site. It’s charismatic without being showy, and (for me) aspirational but restrained.

It seems from some of your comments that it isn’t the easiest thing to wear insofar as pairing are concerned, but I hope you get plenty of use out of it still.

JJ

Very nice article! What do you think of the Himmel suede jacket now that you´ve owned it for a while, in terms of quality and style/versatility?

Initials CG

Agree with comment above and glad that the Panico grey flannel remains a favorite.
This was a very enjoyable read, and I hope you expand on it as time passes. Perhaps our preferences for wearing certain pieces evolve as we do and the world around us changes. Yet many of these remain classics.
Am I wrong, or are many of your favorite combinations parts of a complete suit? For example, the herringbone grey tweed jacket was part of a suit, or the cream linen jacket… I wonder if that’s sometimes a conscious decision on your part to have suit made that can be separated and used in different contexts?

MW

This post is one of my favorites! The outfits are terrific. I think you really summed it up: we “want to have good clothes they can put on every day, and look good, without having to think about it too much.” We don’t want to be peacocks or fussy!

Rik
Stephan

Nice post, Simon! There are more great stuff from earlier years. This one for example has always been very inspiring to me: https://www.permanentstyle.com/2015/07/wearing-colour-tobacco-jacket-and-cream-trousers.html

Miles

There seems to be a common thread in most, but not all, of these photos: your choice of suede footwear. Although this is somewhat coincidental, the texture of your footwear, along with your beard, creates up-to-down cohesiveness with whatever else you’re wearing. It’s a simple and maybe obvious point. It’s actually like your desire for a higher collar. They’re both fairly minor style choices, but taken with the whole have great visual impact.

A lot to gain from this article. Thanks.

Paul

My friend, if I had a photo of myself like the one of you in sunglasses and the DB jacket, I would have it framed. You look like 706,315 pounds or the American monetary equivalent.

Anonymous

Where does the suede cap come from? Do you have a post about it?

John

Hi Simon,
It may sound surprising to you, but for men like myself, it’s hard to answer the kind of question you’ve raised in this post. Why? because we are context-centered.
As a general remark, I would just add that mens’ minds are wired in such a way that they merely can’t effectively manage a wardrobe beyond a definite scale (variable, of course). Contrary to women whose cameleon-like minds allow them to get away hopefully with anything they choose to wear.
For men, beyond a certain limit, there is something like “a disminishing return in investments” at play. For they are quickly overwelmed by sheer volume. All those who claim that they do possess, say, 40, 50 pairs of shoes can’t be effective anymore sartorially speaking, unless they resign themselves to merely taking a pleasure by just watching from to time to time a great deal of items they have amassed over the years, and the pleasure associated with any of them back at the time of its purchase.
If you were to make a survey over “which are the posts PS readers have liked the most”, you would certainly find more belonging to the first group who would then mention all the ones related to “capsule” building, while being caught flat-footed when trying to comment on a post such as this one.
John

Chancellor

I’m wondering if you could comment on the warmth of the coat you had made in Tengri. Would it be warmer than a wool coat of the same weight of cloth? How about cashmere?

I’m thinking that when I get to commissioning overcoats, I will want a very heavy cashmere or alpaca coat to deal with the very cold Canadian winters I experience (if you have other suggestions for material, please do offer them).

I’m wondering if this Tengri overcoating might be a good option for warmer periods of winter or late fall when it is just below zero celsius. Recognizing there’s a premium cost for this cloth, I want to make sure I target its usage appropriately.

Laurence

Hi Simon,
I’ve been reading your blog for a very long time now and it has been so nice to follow you in your journey of finding your very own personal style. I always enjoy how you think about colour, and it is interesting that most of these outfits are so very muted – what you described before as the cold-colour capsule and adding blue. Great to see that such a great post originated from a reader’s suggestion, so if I could make another one: Which colours work best in a Zoom Meeting? Would be nice if you would share your experience on that.

Mark

Hi Simon, I really like the things you wear with the Ciardi gun club jacket. The texture and color of shirt and trousers work perfectly with the jacket. Maybe it is a little bit bold so you didn’t choose it?
https://www.permanentstyle.com/2020/03/the-t-shirt-under-a-shirt-and-tailoring.html

Dan James

So many of your choices are coincidentally those which I like so much myself. The Bridge Coat outfit (always thought the trousers were dark grey-time for another eye check!), the Anthology Herringbone suit worn as a suit or just the jacket and the outfit worn for Pitti.
If I may, there seems to be a common element in the photos in that there is a look on your face that comes through the photos. Whether its confidence that you have made the right choice, feeling content or comfortable in them or just plainly happy in what you are wearing. To me that is half the battle-looking good and feeling it. Added to that, there is something that is almost indescribable about it and people feel the same without being able to put their finger on it.

Haackk

I have to say the outfit in the Navy jacket with jeans-post is a strong runner up. So versatile and casual. The heavy fabric of the jacket looks wonderful. The suede Dovers are also really nice. Personally I would prefer jeans with a higher rise and roomier cut.

https://www.permanentstyle.com/2020/08/navy-jacket-and-jeans-with-recommended-cloths.html

Dmitriy Yastrebov

Hi Simon. How how do you feel if people start copying your outfits? Because, God, they’re awesome!

Colin

Simon

Just started reading your site and enjoyed this post. Wondered where you purchased the reverse horsehide jacket from. Have suede jacket in a similar tone and wear it regularly also with an old pair of 501’s. My jacket does not have the same level of detail so would like to upgrade.

C

Malcolm Lane-Brown

Simon,
How does one get a central dimple in the knot of a tie ,as you do?

Anonymous

Hi Simon – being short and thin, I think I read a PS comment that suggested that an A&S house style would maybe enhance someone with my proportions; but I’m worried that A&S given its English structure may be inappropriate for a very casual city environment (especially a 2 button jacket that would help elongate the figure). How should one balance these two conflicting factors, and would a different tailoring house work better? Can you somehow get the best of both worlds? Casual, yet slightly form building?

The reason I’m thinking about this is because I saw a small-shouldered and thin man wearing an appropriately casual Neapolitan jacket, but the natural shoulder jacket displeasingly emphasized his small features. Many thanks

Andrew S.

I have always thought the Ciardi dark grey suit with black suede shoes was a subtle, simple and stunning combo. How do you feel about that one in the context of the many others? Cheers.

Nicolas Stromback

My favorite is the tailored look in the how to dress for very hot article: https://www.permanentstyle.com/2017/08/how-to-dress-for-very-hot-weather.html

Will

Some great looks here Simon – quick question – from where is the dark core jacket in the 4th photo down in the ‘extra 5’ photos?