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Everyone gets stuff wrong. We all have outfits we look back on years later, and cringe. 

Fortunately, I believe this is something where you learn and progress. It is not a cycle of fashions, where every few years you wear something different, and dislike what came before. 

I dress a lot better than I did 10 years ago. This is because I know myself more, and what suits me, but also because I know understand better. 

This article is a small reflection on what I've learned, with some illustrations. As ever I'd be interested to hear yours too. 

There's nothing really wrong with this outfit, shot for a Drake's article back in 2016

The colours all work well together, with enough contrast between them, and the trousers are sufficiently dark, which is rarely the case with cords. 

However, there are a few things I would change today. First, the jacket is really a little too smart for those trousers. It’s partly the material (cashmere) and partly the cut, which is the sharp, slightly dramatic style of Cifonelli. 

Although the cords are dark and slim, they’re still corduroy. Something like a charcoal flannel or high-twist wool would have been better. 

Second, the monk-strap shoes are probably too smart as well. A loafer would have been a better choice. Something like my Belgravias would have gone with the cords just fine, while actually also being a suitable partner for the Cifonelli jacket. 

Interestingly, reading through that article five years later, I still agree with everything. 

Its point is that corduroy can be fairly smart if the colour is dark and the cut slim. That’s true, and the colours selected to go with it are all pleasing. 

It’s just that the style of the jacket and shoes is too smart. It’s pushing the combination too far. 

Other small things I’d change are probably swapping the V-neck sweater for a crewneck. And choosing a paler colour for it, so the jacket doesn’t stand out as much. 

This second outfit, from the following year, is similar in the small tweaks it needed, I think. 

The hand-knitted cardigan from Ralph Lauren is still one of my favourite pieces, and I wear it all the time. But not with a polo shirt. 

It looks better with a white T-shirt, just because of how casual and relaxed the cardigan is. And white or even a pale-blue oxford are better partners than a grey piqué cotton. 

The loafers are a little too smart too. As with the Cifonelli/Drake’s combination above, I think the colour combinations are great (pale denim with snuff suede) but the formality isn’t, quite. 

The loafer is the Pimlico from Edward Green, which is on a fairly slim, long last. Something like the Piccadilly would have been better, or even a low American-style vamp like the Duke. 

I have to say the jeans from Anglo-Italian haven’t grown on me over the years either. Mostly for quite personal reasons. 

The carrot-shaped line works OK with jackets, but I find it’s a little too slim-ankled for casual clothing. And the wash looks too artificial to me too. I think this is just because I’m so used to the more organic, personal look that comes from wearing in raw denim, or buying vintage. 

For all those reasons I rarely wear the Anglo jeans anymore - even though the fit was great - and would wear my vintage Levi’s with a look like this instead. 

Oh, and that cardigan looks a lot better unbelted. 

This outfit is only here to illustrate one thing: that I have a habit of buying blousons too small. 

I think it’s a hangover from tailoring, which is so flattering, where you pretty much always want the waist to look slim (even if there’s plenty of room there). 

It took me a long while to accept that the cut of a blouson is the opposite - the whole appeal is the large back, cinched into tight hips. It’s not dissimilar to the contrast between a shaped overcoat and a flowing balmacaan. They’re both lovely - just in very different ways. 

This tendency is particularly annoying because this Ralph Lauren blouson was so beautiful in every other way. And I got it in the sale. And I had the choice between Small and Medium. And I made the wrong choice. 

It took me three years to finally accept it was too small, and sell it on. (And by the way, credit to reader ‘Gus’ who made this point on the article, quite correctly.)

What else have I got wrong over the years? 

Not that much, luckily. I think I’ve largely dressed conservatively, and that’s served me well. Even back when this site started, 13 years ago, I tended to prefer simple, dark combinations, what we called the ‘Italian background’.

I did buy too many Prince-of-Wales suits (above). That was an early obsession. I also bought too much structured/dramatic tailoring, and probably had too many things double-breasted. 

Basically, I did what many young guys do, if they like tailoring, and chased the more exciting purchase over the more useful one. Something Aleks and I discussed a lot here

The same motivation was probably why I tried so hard to make waistcoats work. They’re just so flattering, and elegant - but unfortunately look more and more anachronistic.  

I also pushed for dark shirts to work under tailoring - especially dark denims (above). But they just don’t look that good unless they’re the enzyme-washed kind. Better to accept that RTW, or just wear navy under navy

Looking back on those old images, I certainly wear glasses a lot less than I used to. Although I still love them, I think I’m just better looking without. The only ones I do wear are the Bonnet acetate and Eyevan wire frames

Finally, advocating wearing the collar of this Caraceni jacket up was a mistake. That look works as an occasional, functional move - when a cold wind whips down the street. But not as a default setting, and not in tailoring this formal or summery. 

Interestingly, I find I dress more simply today than I used to - certainly when it comes to tailoring - but I'm no less excited about what I wear. 

Instead of double-breasted Prince-of-Wales suits, I get excited about the shade of a yellow oxford. Instead wearing a fedora, the patina on my loafers. They’re more subtle things, but no less enjoyable. 

Perhaps the most obvious sign that this journey has been a progression (rather than going round and round in circles) is that I find I’m more often complimented for wearing outfits that feel familiar, tried and tested. 

They’re not exciting and new, but they looked good and continue to look good. Something like this cap, coat and cream below. There is a very particular satisfaction in that. 

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Peter Hall

I really like the first outfit! Monks can be a tricky shoe to match. I very rarely wear mine-perhaps they have been replaced by boots. I agree about the blouson. I’ve always considered them a ‘shoulder jacket’ and wear with the bottom button unfastened. Luckily, I have quite wide shoulders and I think they sui the beefier chap.


A lovely reflection Simon,

May I add that I see nothing wrong with the cardigan/jeans combo. I believe this to be one of my favourite outfits on PS. Interesting how two people’s perspective on the same outfit can be one of regret, and one of inspiration!

Would love to see the opposite of this post in the near future “outfits I got right”.



never realised you had a lookbook page..very nice!


I’ve been reading your posts for over 7 years and didn’t realise this website had a ‘looks’ page !

I think its true that most readers never get further then the newsletter and shop pages


the looks page is such a fantastic resource for ideas, i would suggest adding filters or tags such as summer, casual, outerwear etc. Even brand names


Great news! I tend to use the site to search for looks I have a vague recollection of. Tags on the logbook will be very useful indeed.


Nice article, although i feel some of the points raised verge on the neurotic which is not a good ‘look’ when it comes to dressing. Often i find the most stylish men don’t have anywhere near this level of detailed consideration and its often the things are are slightly wrong, out of place or mismatched that really make the difference. This level of consideration is great if you want to dress by numbers but i fail to believe it achieves anything more than text book box ticking at the detriment to real character.


In a word: sprezzatura!

I can understand both points, although to me Simons’ points seem to often err on why a more relaxed, simple element would have been better than the formal one used

The Iron Dandy

I do agree that the “mistakes” in this article are nitpicky to the point where if it was written by anyone but Simon I would feel it was humble-bragging (Simon gets the benefit of a doubt because he consistently writes to this level of detail about most outfits). But on the other hand, I think this level of nitpicking shows why PS has remained such a useful resource for so long: Simon isn’t the only guy on the internet posting good outfits, but he’s one of the few who actually break it down to this level of details and dispassionately explain WHY he feels something works or doesn’t.


Interesting article you, thanks. So you don’t wear your fedoras any more? Or you do wear them but are not excited about them?



Thank you. This is a superb idea for an article. We’ve all been on this journey with you!

A few other examples immediately spring to mind. It would have been nice to see a couple of these included and discussed:

The purple Liverano sportscoat (at Lord’s!);
the Huntsman shooting suit (and the subsequent spat with the tailor);
the ankle-length overcoat from Sexton;
Native American jewellery; and
the forearm tattoo.

Best wishes,


It would be great to read a post where you would point style difference that the shortening made. I have loved the style of the original coat (it was one of the first post I read on your blog) and never understood why you decided to shorten it.


That’s an interesting comment on the ankle length Sexton coat. I too have an ankle length coat, two actually, and have been considering shortening them. What went into your decision to shorten your coat and how what is the new length?


Hi Simon, I think this article summarises a few of the most useful things that PS has taught me over the years. Firstly how to interpret the relative formality of certain garments, and then how to put things together whilst generally keeping to the same level of formality throughout any outfit. I think this always gives the most success, and I always seem to come back to the ‘seven levels of formality’ article.

That said, the high/low dressing ideas introduced elsewhere are also interesting.


Exactly, but getting those fundamentals right to start with is not always evident.

On the point of dark shirts under tailoring, you used to wear mid grey shirts quite a lot, particularly under grey jackets. Do you still like that look? And does this apply to the Friday polos? I always liked the darker colours, the brown and dark green etc. under tailoring, albeit more casual jackets.


Well Simon whilst I do agree with many of your observations on the outfits considered here, it does strike me that our personal aesthetic appreciations, given their tendency to change over time, are as much about our personal psychology constructing a sense of ‘rightness’ or ‘wrongness’ in relation to such combinations, as opposed to any sort of platonic ideal of what looks right. If this makes sense?


Out of interest how have the Anglo Italian jeans aged? Have they faded on the thought? ( I like them but tend to look for more aged/ faded )

Wouter de Clerck

Simon, you write that you can recommend AI jeans for their excellent fit. Could I ask if you picked the same inseam length as your Levi’s? I am keen to buy them online, but undecided on what inseam length would be good for me. I already emailed with AI and they provided helpful input, but I would appreciate your feedback as well.


Hi Simon.
You mention in the article that the AI jeans have not grown on you. Can you share the reasons? I have two pairs and what I found is that one of them has a fuller leg for some reason while the other fits me well.

Aloysius Meers

I always wonder how you can so often wear RTW items in size medium, let alone small Simon. Wouldn’t the arms be too short given your height? I am the same height as you I believe (just over 6ft) and have relatively short arms, but still need to take a large in most RTW to get the body and arm length to be adequate.


Hello Simon, really enjoyed your reflection!

Actually, the first outfit would probably have worked better with a simpler light coloured rollneck sweater and yes, slightly more casual loafers.
But I particularly enjoyed your self-criticism, great way to reflect on oneself !

Do you happen to remember what is the colour of the EG suede loafers in the second look?

Although, would love to see an article on the outfits you’re the most « proud of » or felt most comfortable/appropriate.

Kind regards


What about your double breasted denim suit from Cifonelli – would you not regard that as a mistake? I don’t remember you ever posting pictures of the jacket and trousers together.


Firstly , good article and more of these needed.

None of the outfits look too bad except the second one .
The second one has aged badly but then it was never even of it’s time.

I think what this article perfectly illustrates is how easy it is to get things wrong when you complicate things.


So, what is your stance now on double-breasted jackets and v-neck sweaters in general? DB suits look great, but for a more casual wardrobe, it’s difficult to find options. DB tweed jacket for chinos, jeans and cords? And v necks look lovely under conservatively cut DB jackets (I believe I’ve seen a photo of Camus somewhere wearing this, and it was great), but not under SB I think… Here a Drake’s style cardigan seems to be a better look, ot perhaps crewneck for something different. At least that’s what I would say…


Another thing that I noticed while looking at old photos is how much better layered outfits looked with neckties. It’s not about being proper or formal or none of that nonsense, just aesthetics. V-necks, waistcoats, cardigans, all that looked better under jackets when the shirt collar was closed by a tie knot. With an open shirt, things get hard. Waistcoats are out of the question, v-necks are harder, unless under an overcoat. With just a single-breasted jacket and and open oxford shirt, for me it seems that only slim cardigan works for that “sharp” look. Crewneck just makes it a different thing entirely – it looks more casual, maybe because almost the whole shirt placket is covered and the V shape is less prominent. I recall seeing Drake’s doing that now with pastel-colored sweaters. It kind of reminds me of contrast collar shirts. Those were all the rage during Pitti Peacock days, but no one wears them anymore. Not a bad attempt to revive the look, I’d say


Great article, although the comment about glasses made me sad.
If you love them – why not wear them? If it is because you are better looking without that screams vanity, over style / function considerations, to me.

Avid follower but would love an honest with the self article about vanity. I think you have got considerably more vain, but hard not to when in your field. Would be good to hear thoughts on it though


I think that your glasses are really lovely – great make, colour etc. It just seems to me – that almost all of them are just a tiny bit to small for your face, if you allow such comment. The wire ones – look superb – because both size and shape are on spot. I suppose that the “aviatorish” shape works much better than the small round one on your face. It’s just a thought, and I can be completely wrong on this one.
Kind regards


Vanity is an excessive and unhealthy pride or care about one’s appearance. Having an interest in one’s appearance is not vanity (if that’s the case all readers of PS -and indeed most people- are vane). On that basis Simon doesn’t come across as vane. Indeed, he does stress the point that as interesting as we may find clothes, they are not important.

Regarding glasses, I got a nice pair from general eyewear (on the basis of your review Simon). They’re certainly nicer than any pair I’ve had before. However, I have to agree that no glasses just look better. I do wear my glasses most of the time simply because I’m too lazy to put contacts on and having them for prolonged periods dries my eyes. Nonetheless when going out I do usually wear contacts (not much of an issue these days).


Very good post, Simon!

I completely agree with the point about waistcoats becoming anachronistic, no matter how incredibly painful it is for me to admit. They are very practical in cold weather and are indeed so flattering, extending the leg line and simply putting that finishing touch to a suit. Not to mention how attractive and manly they look with the jacket off, provided of course they’ve been cut well. Initially, I stuck to my guns and always used to wear one but, alas, one just becomes “that guy” – similar to people wearing braces or bowties. I work in what should be a very formal office in the City and (back when we were still going to the office) I used to get almost daily comments about wearing a tie – the “you look very smart but please stop it because you’re embarrassing us” type. I’m not ready to give up wearing a tie with a suit just yet but I can only imagine how horrible it would be if I put a waistcoat on!


It feels like 2 levels. One strategic, observations on improvement/better. Second, the more personal one, where we observe the world around us/trends and find attractive and attempt to adopt, but find uncomfortable or just not feel like a good fit. Like the observation on the fitted v too small, which I find a continuing lament/issue.


It’s interesting that you chose these. I think some of these are pretty good and some have been much worse.

I like the Solito with the denim shirt. On an intellectual level, the first outfit has a number of things wrong–it is hard to wear light grey jackets, cords are hard to wear with tailoring and with more formal shoes–but there is so much going on that I honestly don’t think it looks bad at all. If you throw a bunch of things together that aren’t very coherent, sometimes the outcome can be pretty coherent. Once you take the coat and scarf off that may be a different story. The cardigan look isn’t one I would personally go for, but I think it looks good on you. I don’t think a t-shirt would look better than the polo here. I agree that the blouson is pretty bad, and that the db with the collar up is strange, but overall, I don’t think this is such a bad selection. Some of these outfits are quite good.

There are others you have posted that are far worse. I think you do a lot of experimentation on here and this will invariably lead to some pretty bad pairings. That being said, I think this experimentation is instructive even, or perhaps especially, when it goes wrong.


Honestly, to an untrained eye, these “bad” outfits look better than most people’s “good outfits!” However, what inspires me about your style is the understated elegance. The second look goes overboard but it’s still cool (at least on a lookbook) although the t-shirt would have fit better. And perhaps even, white socks, just to make the style statement very clear! The first look still looks polished, but affected. There are too many “strong” pieces at work at the same time. It’s one of those looks that look great on Instagram, but that in real life, even in the most formal situations, I wouldn’t see myself pulling off (or anyone else).


Hi Simon, Another very interesting and refreshing article. Credit to you for stepping outside the safe zone and taking a critical look back, rather than some other sites that tend to drive simply to making more purchases. It’s useful to know I’m not the only one who gets it wrong sometimes!
Building on some comments about guys getting it right even though on the face of it something is wrong! As with many things that appear intuitive, what is apparently happening is experience coming into play at an almost unconscious level. Also keeping it simple and minimising/ optimising choices makes dressing appear less ‘strained’.
The point you make about compliments on the outfit in the last picture, may to some extent come about because you feel comfortable and confident wearing it and that comes through (just a thought). I think it’s great look too.
For myself, many of my mistakes have come from sizing in either direction. I’ve learnt with tailoring best to size up and alter down as required. Also from just not keeping it simple!
Finally (to my shame!) as with a number of other readers I didn’t realise there was a look book section on your website. Very useful and interesting suggestions in it.
Thanks again.

Dr Peter

Nice article. It is unusual to hear someone discuss mistakes and talk about how one learned from them.

A small point: With corduroy, I think the finer the wale, the more formal the item of clothing can be. Pinwales are more formal than widewales, to my eye. They can be paired with blazers and solid or small-pattern sports jackets. This is also in keeping with a general rule of thumb. Smaller patterns (and even textures) in shirts, ties, suits and sportcoats tend to indicate greater formality, and larger ones suggest dressing for the country.

Ben R

Could you point to a picture of how you think a blouson should ideally fit?


I have a couple of Valstarinos and whilst I like them they do seem to have long arms.Do you have the issue?


Reading your observation about blouson sizing and the comments, I was going to comment exactly this. I read both reversible valstarino’s posts when published, and I always thought the fit of the brown one (size 52) looked better on you. At least that is the look I would go for when I have the opportunity to buy a valstarino for my self.
Anyway, good post as always.


Hi Simon, your comment on the Anglo-Italian jeans is a bit unexpected to me. Wouldn’t in general a slimmer fit (and ankle) work better with casual clothing rather than tailoring?


I see. So can you please elaborate on what makes those jeans not work with more casual outfits?

Tommy Mack

Definitely lots of strong pieces catching the eye in that first outfit. I was going to say fighting for attention but actually, it’s quite harmonious despite the bold choices (although I agree with all the tweaks you suggest in the article)

If I could only change one thing in that outfit, I think it would be the starkness of the black v neck and white shirt against the grey of the jacket and cream/off-white scarf. As you say, a pale crew neck would offer a softer look.

If there’s a problem with the second outfit, I’d say that the colour of the jeans seems a little too close to the blue of the cardigan for my taste. I’d be tempted to go for more faded jeans or very light beige/stone chinos.

As many others have mentioned, these are very minor tweaks and i don’t think I’d have considered these bad outfits if you hadn’t drawn attention to them. It’s very interesting to think about what does and doesn’t work and just as importantly, why.

I’ll have a think about any relevant satorial misadventures of my own I can share!


This is a wonderful article Simon, thank you. Cary Grant made the observation that simplicity was the essence of good taste. It appears that you’ve trended more and more in that direction over time and taken your readers along with you in that direction.


‘I did buy too many Prince-of-Wales suits …’

This is understandable. There are plenty of RTW suits with two or three buttons in dark business colours. If you are going bespoke there is a temptation to go for cloths or features that are not readily available off the peg.

I would love to find a Prince of Wales suit with a blue overcheck in a quality cloth and decently cut. Unfortunately most RTW suits are aimed at the business market.


The Ralph Lauren suede blouson was sublime; I actually spend a good while trying to find one after I saw it!! I don’t know if it’s a suede thing (given there is little or no stretch) but I’ve often had an issue with getting a good fit in RTW suede and have found that the sizing can be really inconsistent, even within the same size. Worth the hassle though!!


Great post. But c’mon, that’s the best you got? Pretty tame. I’ve seen much worse. I’ve worn much worse. Visualize a circus tent sized jacket with navel level lapel gorge and condor wing wide shoulders matched with a Vicki Davis string bean tie (is she even still alive??) ….. finish it off with parachute pants in a material not found in nature. But it was the 80’s. And btw, I love the Liverano purple jacket. The Huntsman shooting outfit was a risk, but life begins at the end of your comfort zone. As a father you of course know that. Have a great weekend.

Frederic Patenaude

… about the glasses. I think the problem with your glasses was the shape, too round, giving a professor look. I wear glasses so I’ve tried many shapes and something like Mr. Leight Getty C might look good on you.


Re: the first outfit, I have to say that I’m a bit surprised. I think the rich color of the trousers is a lovely contrast which keeps the outfit from feeling monochromatic; and the drama of the jacket is hidden by the overcoat in all the shots, so for me that didn’t come through. I agree on the monks, but then I don’t like them (or tassels) generally.

Patrick Bateman

Shame about the RL blouson. Could you not have just worn it open?


As someone who has tortured himself with contact lenses for years before going back to glasses, let me tell you this: If you think you‘re better looking without glasses, you just haven’t found the right glasses yet.


I found the blouson observations very interesting. I still don’t quite understand the reasoning of why it differs from tailoring but it is certainly true when I look at the photo.
Do you think perhaps it is also an example of a photo showing you something you didn’t see in the mirror (something I’ve certainly had before)?

Daniel R Estrada

Yeah, I bought some stuff that I do not wear anymore or regret. One is this MTM overcoat I commissioned. I did not like the colors offered for overcoats, and so, I went with this nice blue colored flannel suit cloth. I asked the sales guy and owner if it would be heavy enough for winter wear and they said yes. At the time, I had no clue about fabric weight. Well, it is not. I cannot wear it below 60 degree weather without a sportscoat and sweater underneath. It’s aggravating because for MTM it was not cheap. I would have been better off just buying an overcoat off the rack.

Also, I have a pair of corduroys that I just do not like how they hang and the hem needs to be made shorter. Also, some of the pants I have bought I do not wear because I find the rise too low. Oh, and I tried this MTM tailor who took crappy measurements and made me a suit that is too small.

These experiences make you sit down and research more and be wary of MTM outfits that are just looking to sell and make money.


Don’t you regret the Biagio Granata summer grey jacket, too? I think you wrote it was cut too short, etc. Also, I am not a fan of the Ciardi vintage gun pattern jacket. Just do not like the pattern and cut. As for the Liverano purple coat, I am conflicted on that one because it is a nice purple shade and cut. Do you ever wear it with jeans?

Nicholas John Collyer

Makes me cringe to think of the times I’ve thrown together combos of expensive, rare and beautifully crafted items that in retrospect did not fit with each other or the context. Appearance is everything, and nobody in the street, at events or at work cares about things that are super important to someone who likes classic style – who tailored a jacket, the brand of fully fashioned knitted sweater, the mill for a tweed, the weight or source of a linen, or a shoemaker’s skill with a pig’s bristle mean nothing if I look like someone’s well-heeled but eccentric grandfather who dresses in the dark.

Adam l

Love the first outfit to be honest. Fantastically louche vibes.


Interesting point on the glasses. I probably wear mine more now, for the same reason you wear yours less, I think I look better with them.


I liked this piece. Admitting to mistakes/changing your mind is the first step to self-improvement, and can be very relieving, even thrilling. I felt great sympathy on the suede blouson mishap. I love RL purple label but full price is out of my range, so I’ve faced that Small or Medium sale price dilemma a few times. My worst mistake to date is a beautiful cashmere jacket from Aquascutum bought impulsively at Harrods a good 5 years’ ago and never worn – just too big. I was mesmerized by the fabric, and soothed by the reassurance of the salesman. Should have taken my better half, she would have spotted it immediately. Live and learn.


Regarding fit, I think there’s still a (waning I hope) tendency to have every garment fit slimly. Too slim and you run the risk of having a garment that looks too constricted and less flattering.

I agree that causal pieces like blousons (even more so in suede) are particularly affected. When I bought the PS reversible valstarino (can’t wait for spring to wear such a versatile jacket!) I agonised between size 48 and 50. Fortunately Simon you had pictures wearing two different sizes (the blue and the brown), helping me see this point before this article was published.


I don’t really get why you think the blouson is too small. It looks perfect to my eyes, trim fit as the WW2 aircrew uniform it is inspired from.


Great article Simon. I agree that a journal detailing outfits that best represent you would make for a good read.

In reference to the jeans, I recall you saying that taper in jeans is usually a matter of style. I am looking at getting a pair of Blackhorse Lane jeans, and I am torn between the NW1 and the E5. Both have a relaxed fit, but the E5 tapers from the knee down. The NW1 also has a high back rise, where the E5 seems to be a balanced medium rise. Do you think that makes the E5 better with tailoring and less balanced in a more casual ensemble? Or is this too limiting and both would work for the same range of smartness?

Denis Turecek

I love these posts, Simon. If someone comes looking for advice of what to wear or how to wear, I think it’s important to not only tell them what’s good, but what went wrong as well. And, of course, tell them why it wasn’t success. I find these posts pleasant as most of bloggers are trying to tell you what to wear, but never shows the opposite side of it.

Btw. that RL cardigan, I can’t help myself but can’t get used to see it on you.. It seems to me as way too casual in comparison with everything else you’re wearing, but that, of course, may be my subjective feeling.


Soo, is the Ralph Lauren suede jacket sold already or on its way to a new owner? And by the way, was it a RRL or Purple Label or else? If by chance, you remembered.
Would love to see it appear on Marrkt as it’s my size (obviously).

It is always very enjoyable to read your reflections. An article on the outfits you love to wear and often go back to would be very interesting as well!


Best article in a long time, for its typical PS frankness, originality and good sense. Thank you.

I accept the progression thesis. But oh how frustrating that one is often too stubborn to recognize a mistake. In my case buying shirts and trousers that are just a bit too tight once again.

Tommy Mack

My sartorial sin is not so much size but colour: buying lots of brightly coloured polos, knitwear and even trousers because they caught the eye (and often because they were heavily discounted in sales)

I’ve gradually learned to look at new clothes as potential components in my wardrobe rather than as beautiful objects in isolation (after all, nothing which is useless can ever truly be beautiful!)

Another consideration is suitability to lifestyle: I love off-white/cream knitwear and trousers but there’s no way I can wear it around my young children, so for now I have to accept that any whites in my wardrobe should be machine-washable!

Pamela Stewart

The second look definitely a dark tee, dark wider legged jeans longer (those ones have a odd color wash and almost look pegged). The shoes definitely should be a rugged Oxford maybe a luggage leather or chocolate brown suede with a thicker hiking type sole. Speaking as an American woman! I subscribe and enjoy your newsletter read it to my husband and forward to my son. Great photos.

jef dej

i’ve been a long time reader but never commented. it struck me now, reading this piece, something that’s always been a bit of an irritant and that is nothing here ever seems natural or effortless. i suppose because the raison d etre of the site is the ‘look’ of the clothing that everything that eventually makes its way here has been studied. and studied. but as one of the ideals of fashion is for it to truly merge with the wearer and disappear, how is one to deal with this paradox. it’s just that virtually anything on here from a shoelace to a lining to a jacket gorge is analyzed ad nauseum. i dont know…does anyone how to be interested in clothing but not signal to the world how obsessed on may be with it.

Dan Kohler

Hi Simon – great post. Love your lack of ego. I’ve been a reader for a while but my first time commenting. I love that Ralph Lauren leather jacket. Can you provide any more description or detail on it? Anything else that could help me find one on eBay I guess is what I’m asking for if you don’t mind.

George Blumfield

Thanks for the posts; always interesting, although I don’t understand some of the terminology that UK residents use to describe a situation or items., although most of my family were immigrants from Scotland. Best wishes and thanks for the posts,

Matt H

I’m pleased that you mentioned the Caraceni with the collar up. I’ve always thought that seemed like an odd thing to do with that jacket (I see the photo fairly regularly here and there).

On the whole, I’d say you’ve done well to not have any serious cringe to look back upon.

You mention that you got too many PoW suits, which leads me to a matter that I’ve wanted to raise. You do appear to go for a lot of the same colours over and over again. Now, I can appreciate wanting to get things in your favoured colour palette in various different fabrics for different occasions, but it feels like there is a lot of repetition. To me it feels like wasted opportunity.
Occasionally you’ll throw caution to the wind and end up with something like a pink Orazio Luciano jacket, but there are many options for restrained, classic colours and patterns that you don’t seem to have tried.


Interesting, I would have thought that the Russian hatch grain ones were far more versatile, not needing so pale colors elsewhere. They are really lovely…


A habit of buying jackets too small because you’ve got tailoring fits in the back of your mind is something I wholly sympathise with. I have a bunch of leather jackets like this.

In a particularly egregious error, I have a PSxPrivate White trench coat that’s has none of the upper body billowy charm it should have because I was a doofus.


heres an idea: i think you’ve had this blog long enough to cover a menswear trend cycle. maybe you can highlight some looks from the early days which wont fly now, simply because they’re out of fashoin/ubiquitous/look dated/anachronistic. it would kind of go against the ethos of the website, but still would be interesting to know.


I’m inclined to disagree about the blouson – it’s a great piece but probably might have worked better with heavily pleated trousers – perhaps more of a Bowiesque motif .
With all due respect – I never did get the Ciffonelli thing – I just can’t visualise what it is that people keep banging on about.


Hello again Simon. Yes I did read the Ciffonelli article – I was going to reserve my judgement on that one but now you have mentioned it. I noticed that the sleeves were pitched to high and that the sleeve lining was short
I am sure that you are already aware that you have a professional readership who will notice these things more readily than your other followers. Detail means nothing without the basics.

Varun Saxena

Hello Simon,
I just got some linen trousers made in dark green and rust colour (with turn ups of about 1.5 inches). I am a colourblind blind guy (about which I had a discussion with you once, earlier).
I really love the fit of the trousers but am unsure about what colour shirts and shoes that will go best with them. It would be nice if you could throw some light. Also if you could talk a little about what kind of shoes as in oxfords, loafer etc that would make the entire look either formal or casual.

Varun Saxena

Thanks Simon.
Would a solid white shirt not be the safest bet? But perhaps pale blue would look better, as you mention.
Now that you mention a black and dark brown trouser, what colour shirts do you think best go with the colour pants?
what is your take on all this based on the complexion of the guy. That too at times plays a role, I guess.

Varun Saxena

Thanks. Wearing brown loafers today. ?


Hi Simon, would you wear a dark brown herringbone sports jacket (almost like your WWchan’s dark brown tweed jacket) with dark green/olive corduroy trousers?

Many thanks,