How my jacket style has changed

Friday, November 12th 2021
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In recent weeks we’ve been talking a lot about reflections on bespoke over time; the lessons I draw from commissioning tailoring for 13 years or so.

We did an article on how dramatically tailoring can be altered, using my Chittleborough & Morgan suit as an example. I’m planning one (following reader requests) on the pieces that, despite alterations, I’ve grown out of. And there was also our recent article on how my winter wardrobe has changed

These articles are satisfying to write, as I feel they offer more informed and objective advice. Bespoke has to be a long-term investment if it’s going to be worth it, and these pieces assess that from personal experience.

Today’s article is in that same vein. 

I commissioned the suit below from Whitcomb & Shaftesbury in 2015. Six years later, I commissioned a jacket, but with changes to the style to reflect my changing preferences. 

So what were those changes, what do they say about fashions, and how much do they undermine the argument for bespoke that is meant to last a lifetime?

Bigger

The most significant change was for the jacket to both look and feel bigger. 

Now some of this was because I had put on weight (both muscle and fat, mind you) in the intervening years. According to the measurements, about 1.5 inches on the chest and 1 inch on the waist. 

But this didn’t actually affect too many of the style choices. These were mostly about shoulder width, waist button and lapel shape, and weight changes mostly affect the size in the chest and waist - even the shoulder width is relatively unaffected. 

The desire for size was more about wanting a jacket that looked shaped - elegant and flattering - but also very comfortable. I think a lot of us have felt this desire for comfort in the past 18 months, and the fashion has decidedly tipped towards larger silhouettes at the same time. 

It was this I had in mind when I asked for the shoulders of my new jacket to be wider (⅜ of an inch in the end) and for the larger chest and waist to tend towards roomy. 

Wider

The fashion aspect of wanting a larger-looking jacket also drove other changes. 

We know from analysing the cuts of suits that the front of a jacket can be thought of as an ‘X’ shape, with the top half being the line of the lapels, the bottom the open fronts, and the crossover the buttoning point. 

If you want to look larger in the upper body, you increase the top of that X by widening the lapels (and the shoulders) and lowering the buttoning point. With my Whitcomb jacket, the lapels were widened from 3 inches to 3¾, and the buttoning point was lowered by half an inch. 

Requesting wider lapels was also a pure style point, unrelated to how it makes the body look. It’s something I’ve favoured for a while on any style of jacket, and the original Whitcomb lapels were unusually narrow in that respect. 

Longer 

Only a little longer. A half inch at most. 

The problem with any changes to proportion is that you have to keep the jacket in balance. I’ve seen newcomers dramatically alter proportions on a bespoke commission, only for the buttoning point to look like it’s over the groin, and the skirt little more than a frill. 

So always err on the side of caution. Look at the jacket as a whole, and consider that it must remain balanced. We’re not actually aiming for a piece of fashion here - the test of that being, perhaps, whether anyone unversed in bespoke notices the choices you’ve made. They shouldn’t; they should just think it looks good.  

So with this Whitcomb jacket, it wasn’t that I wanted it longer necessarily. Just that it looked much more harmonious when it was. 

A good way to test that is considering where you’d place a second button, below the waist button. If it would look comically low, then you’ve done something wrong. 

Even with my jacket here, I decided to leave off a second button because it would have strayed too far down the curved openings below. But that was more about that curved shape than about the length.

Rounder

Which brings us onto the last point, which is that I wanted the jacket to be more casual - which often means rounder. 

Those open fronts below the waist button were a little more curved. The lapel was cut straighter, so it curves slightly outwards as it runs up the jacket, rather than inwards (as the previous suit had done). And the shoulders were more natural. 

Whitcomb, like a few other English tailors, has started doing an ‘inset’ shoulder as an option on its jackets. This means that the sleeve looks like it runs underneath the shoulder where the two meet, and is what the Italians refer to as ‘spalla camicia’. 

More importantly, there is also less roping at the top of the sleeve, so the shoulder runs down naturally into it, without the little ridge you can see on my previous blue-flannel suit. 

There is also no gathering at the top of that sleeve - sometimes called ‘shirring’ - and I’d still emphasise that this is not a Neapolitan style, not one I’d wear with such casual things as jeans or chinos. Rather, it is a softer, rounder English jacket. 

More transient?

So those are the changes I made, six years later. Does that mean I now dislike my previous suit?

No. I still wear it and I still like it. It’s not perfect, but then few things are if you have and wear them for long periods of time. And there’s an emotional connection to a loved piece of clothing that’s just as important as anything else. (Worth reading Bruce Boyer on that topic, here.)

The changes are also pretty minor. The thing that makes this a question of style really, not fashion, is that they’re a matter of a half inch here or there. (A half inch! Everyone else has switched from jeggings to voluminous sweatpants, and you’ve changed a half inch!)

This is helped by the fact that menswear changes less than womenswear, and smarter clothing changes less than casual clothing. If you favour elegant menswear, you have to change least of all.

It’s also easier as you get older. You become more settled in your style, and novelty is less attractive. I think an intelligent dresser still recognises fashions, rather than dismissing them out of hand. He likes to remain relevant, and takes pleasure in being just a bit better dressed than everyone else. 

But the changes he makes in the name of fashion, are small. Wearing one pattern of knitwear more than another; tweaking the shape of shirt collars. Savile Row tailors will happily tell you how, in the time they’ve been working, fashionable lapels went from 6 inches to 1, but their house style only moved from 4 to 3. 

This is the context in which I updated my preferred cut of jacket. I hope running through it has been interesting, even useful.

The jacket pictured is made in PS Plaid, a cashmere check that we created with the mill Joshua Ellis. This has recently been restocked, and is available on their website, here.  

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Michael

Haha, my aim is never to be ‘a bit better dressed than everyone else’, what a strange motivation.

Michael

Slightly differantly perhaps, it doesnt need to be measured as better or worse. Its not a competion.

P.A.

I believe it is a matter of intention, rather than outcome. Michael does not want to dress better than everyone, yet he probably does nonetheless.

Fred

maybe it should be ‘a bit more stylish than everyone else’
if it is just about being different you can stick a traffic cone on your head

Paul

First ever comment on PS that’s made me laugh out loud. Nice work Fred.

Michael

It depends upon your frame of referance as to who dresses better or worse. I would go as far as to say the PS perstpective isnt any a better or more valid perspective than anyone elses. Therefor using this as a standard to judge better or worse aginst others who may not be aiming to acieve the same thing, have the same referances, care as much, have different or in most cases lower levels of wealth seems rather arbitrary. And indeed to do the same with someone who does share your viewpoint and aims just seems rather mean.
Cant we just be differnet, not better.

Tim

I’m with Michael here. It reads as a fairly pompous sentiment to be motivated by being better dressed than others, and some of the justification implies that there is some objective rule book which people depart from in their choices, but the rule book is gospel. I read PS because (to an extent) I like similar things, but most of all I appreciate the expertise and how that makes me a more empowered consumer. Implemented into my own life and clothing choices, it becomes purely about how I feel I’m representing myself and not about walking into a room thinking I’m representing myself better than other people.

Patrick

I don’t think the use of better implies “better person”, I don’t think there is any of that at all, but it is still reasonable to pursue excellence in things. You do have a point, however, and I think the difference is outcomes rather than aims as someone has said. My impression from the web site is that the comparison is always with other cuts, fabrics, fits rather than people and the elitism is in the comparison of objects rather than people.

Chris

I’m going to sit on the fence with this discussion , which I think is quite interesting, I certainly understand Michael’s point that engaging in competitive dressing is not a healthy goal for most humans. I don’t think this is what Simon meant, but trying to outdo people who may have less money, less resources etc is somewhat glib.

But equally , I do feel like especially in tailoring the goal is always to hold your head up high in a room feeling well dressed . The other day, at a charity event of people with net worth higher than me in the multiples of many thousands of percent I imagine , wearing my Whitcomb trousers, Ciardi blazer , luca shirt and drakes tie , I felt like an equal.. those items were bought at genuine personal hardship to me but the effect on how I carried myself that evening was profound. Is that a truely healthy emotion? I don’t know, but it helped me through an intimidating evening.

blueboy1967

Hi Simon,
I think this is a fabulous jacket, both in terms of the style and the material. Can you maybe say a little more as to why you don’t think it appropriate for chinos or jeans; is it the pockets for example? If it had patch pockets, I would wear it very casually but maybe I am still learning………….Is it a combination of factors?
Thanks,
Damian

blueboy1967

Thanks Simon – comprehensive answer, albeit, as you note, not easy to be specific with regard to any one factor being important on its own. I still think it would, for me, be a versatile jacket that I would wear with chinos or other casual trousers, if not jeans.

Archie

These style tweaks, more or less, read like a list of features you appeared not to love in your Anglo-Italian jacket review: roomier fit, lower buttoning point, extended shoulder and wider lapels. On reflection, have your early views on the style of the Anglo-Italian jacket, rather than make, changed?

Zy

Just on that note Simon, are you still planning on trying Anglo-Italian Bespoke? Or is that not on your list on account of the above style points?

rafael

For whatever is worth, I much prefer the later jacket and style overall.

Felix

Why do you have these pronounced dimples especially at the right shoulder/upper arm? I always saw this as a sign of poor fit?

Felix

Ah, thx. I have something similar on a jacket and don’t like it – what is actually the problem here and can it be altered? Is the shoulder too wide, or the padding too strong, or is the sleeve too tight?

Robin

Put another way is it that as you’ve got older and more experienced you’ve moved the emphasis more from form to function and looks to comfort .
I certainly like the idea of practicality with jackets more . Which is why I prefer your ELIA CALIENDO tweed which can have its collars turned up and the front fully buttoned to protect from the weather.
The open front of jackets , I believe , is something which puts men off wearing them more particularly in colder weather. Mind you look at 1930’s footage of working men and they’re all wearing jackets with collars turned up .
P.S. really enjoying these slightly different articles , as opposed to reviews of clothes and shoes that few can afford . Much more relatable and useful.

Rogey

I agree with Robin. My tailor makes my wool jackets with a top button. When I turn the collar up and button the top button so the front is fully closed, the jacket really provides surprising warmth in windy and cold conditions.
The cut and cloth of your jacket are superb.

Jan

Hi Simon, this is also a comparison of a suit jacket vs an odd jacket. Would you tweak the jacket style for a suit jacket in a similar style? And, if so also for a suit you‘d wear to the office, ignoring for a moment that you are no longer in the big corporate world?

A (not so secret) Admirer

Simon,

We met on the pop-up opening night recently. I was visiting with a friend and had the pleasure of trying on the Plaid jacket myself. It really was a thoroughly delightful experience to have met you and I can personally testify to all the points (esp. around comfort) that you mention about this beautiful garment. It will be hard to describe using words, but the jacket felt extremely nimble and pliable (despite me wearing multiple layers including a sweatshirt underneath). I have a picture in fact, wearing it besides you, that I intend to keep as reference if I ever decide to commission a bespoke jacket myself.

On a broader note, I also think that such pieces are especially helpful, as it fosters self-reflection, which in my opinion is key to avoiding impulse purchases and the unnecessary wastage that follows (both financial and environmental).

Keep up the great work and hope to see you again soon.

Best wishes.

Con

What I find interesting looking at the photos is how much more comfortable this jacket looks on it’s own but also when comparing it with the blue suit in the second photo. At first when I flicked through the photos I immediately felt that the blue suit looked tight and restrictive, kind of like how guys in skinny suits look.
Of course, when looking at the blue suit on it’s own, this isn’t the case, and it looks like a well fitting and comfortable suit.
As well as the cut, this particular pattern and the colours give off a really warm and comfortable look . It’s noticeable in the fourth photo, that despite not being able to see your face, you appear relaxed/comfortable. It’s not easy to look like that I think usually with hands in jacket pockets – I think the length possibly helps or size of the pockets? i.e your arms don’t look like they are ‘propped’ up/shoulders hunched by having them in the pockets, something I often associate with suits and jackets.

R Abbott

You mentioned that Whitcomb only recently started offering an inset shoulder as an option. Are you happy with the execution?

OTAVIO SILVA

Great article as always, Simon. I’ve been anxiously waiting for it to see the new cut/style you’ve came up with W&S. While English tailors don’t usually use that shirring on the top of the sleeve, a few ones, especially those who favor the drape cut, often put this same shirring on the bottom of the armhole in order to achieve a fuller sleeve resulting in a greater range of motion. I know Tom Mahon likes to do it, so does A&S, I believe. Do you have any experience with that? Does this jacket feature this detail?

Jason

I’ve always been interested in the sartorial and have followed your site pretty much from the beginning.One of the most interesting parts of following your journey has been to see you come to the realisation that fashion revolves but style evolves. This article reflects that.

Fashion Bear

Lovely piece, Simon. I think it’s also worth noting, as someone who tends to retain clothes for decades including many bespoke pieces, that there’s a place in a diverse and distinctive wardrobe for different sorts of jackets, pants and shirts with different cuts, even a vast variety of knitwear (in terms of cut, i.e., knits meant to be worn specifically with high-rise or low-rise pants). Over the past decade, when much of the world was mad for slim, tapered pants, I still wore my full cut Ralph Lauren Purple Label flannels and corduroys from the 90s and early 00s; just as now I still wear slim, tapered denim (though never skinny denim, mind you). It just depends on my mood and the occasion, but if a person is dressing primarily for themselves, there should be appropriate moments for a wide array of clothing styles and fits.

Kenneth

Good Monday morning….you are making excellent points…i too have items that are fuller cut that i enjoy wearing…..enjoy your day and week!!!peace……

Jack Williams

Simon,
A wonderful essay on the changes to one’s clothes as one ages. I wanted to add a little more perspective. I got my first bespoke clothes, a jacket and two suits, when I was in my twenties at Rizzo Tailors in Cambridge, Massachusetts. While Mr. Rizzo himself was still active, my tailor was a young man, Joe Calautti, the same age as myself almost to the day. The jacket cost me $75.00, the suits, $150 each. All were heavy tweed. Over the years, I had Joe make me at least 10 suits and probably a dozen jackets of all materials. As my shape has changed, and alterations were no longer possible, I have given these jackets and suits to my much younger nephews. I now have two suits and three tweed jackets, made by Joe Calautti in the early 90’s. He has retired, but I have had these altered several times. That the jackets have extra material at the back and side seams makes that possible. With several I had the shoulders moved in slightly. but they still fit and look good but softer.
I am 80 now so your six years seems like a second to me. One’s body changes over the years. This has little to do with weight gain as I am the same weight as I was when I was 60, but rather with the process of aging. One thickens, shortens; one’s posture bends forward, all changes that require adjustments in one’s clothes. But also one’s style too changes with jackets and pants that are looser to hide the ravages of time. Softer drape, wider trouser legs, a general blurring of silhouette. This is as it should be, and you are beginning on the journey (at 40) towards a gradual style change. The article by Bruce Boyer you reference follows the same line of thought – and he is, I believe, 80 as well. I would agree with you strongly, that bespoke clothes over time can change and be altered. Perhaps not indefinitely, but certainly over 30 or 40 years. And as one grows old, newer, fewer tailored jackets can suffice and keep pace with one’s body. So from the perspective of a long life, I recommend your younger readers pay attention to this particular essay on alterations, for what you write is true and inevitable.
Again, astute observations of the choices offered to young men as they mature. A great essay.

Jack

Alex M

This is a fantastic post, probably the best I’ve read on PS – thank you Jack

zo

oh wow, how nice.

Rav

Fantastic post Jack – thank you for sharing your perspective.

Ben

As I commented in the original post about the plaid jacket, it looks great and much more aligned with my aesthetic than the blue. Though I would still keep the blue more trim than the plaid because I like bulkier cuts with bulkier fabrics. Some of that of course has to do with the more casual look motivation you’ve mentioned in your post. It’s also that I like my woolens, for example, to feel rich and sumptuous while my worsteds to feel sharp and crisp.

Chris

I really love the cut off this jacket.
For me this has elements of the best of British tailoring (masculine, elegant a La Hitchcock , Gieves) but with the confidence of Neopolitan. Quite special actually I think.

Jerrell

Your post is timely, since I was just having a similar discussion this week with my tailor. We are working on alterations for a suit jacket, and at the moment, it is quite spacious in the waist and chest, whereas I prefer to show off the body with a closer fit. The majority of my clothes, like your Whitcomb suit, fit closer and more streamlined. So when trying on a roomier jacket in front of the mirror, it just feels and looks baggy. It is hard for me mentally (and physically!) to make that fit adjustment.

Vida

Simon,
I prefer the fit of your first jacket. It actually looks like a bespoke piece to me. The second jacket looks almost too big, and I’m shocked that only half inch increments were added in general to the overall silhouette. It just goes to show you how specific and precise tailoring is. However, the plaid jacket not only looks a touch sloppy, but looks off the rack, too.
I thought that bespoke tailing was all about proportion and in the second example the proportion looks unbalanced. Just my opinion.

Colin

Hi Simon…..whilst the changes in actual measurements between the 2 jackets are relatively minor the affect is significant, with the second jacket looking, to my eyes, significantly ‘bigger’; it’s a tricky direct comparison as the cloth is different and less roping in the shoulder always gives a more casual appearance. I am currently having a suit made (suit supply is all I stretch to) which is more aligned to jacket 1, firstly because I like that structured style and secondly because it’s the antithesis to the current more relaxed look, although I should say this is mainly for the office rather than more casual occasions. As a matter of interest at what point in jacket changes (ie: measurement increase) would you then increase your trouser measurements? Thanks

Nico

With that buttoning point it does not seem possible not have been forced to place a second button lower than the pockets upper line. Which is said to look a bit odd, isn’t it?

Dr P

Thank you for the excellent article. I think your plaid jacket suits you extremely well; it conveys a relaxed, confident and mature attitude.
I do not think, however, the rounded shoulders would work well in the suit, but I sense the original blue suit would look better is if it was a touch roomier and longer.
Could I ask if you now also prefer roomier, pleated trousers (to better balance a slightly larger jacket)?

Christoph

Hi Simon,

I really admire how your style evolved over the years, which has been constant inspirations for me.

Actually, I am thinking about making an oatmeal sport jacket these days (like your Elia cashmere or escorial ones, but not that smart). Since cashmere and escorial are slightly too smart for me, tweed seems to be a better option due to its durability and versatility.

Moon’s shetland twill looks great, but there aren’t many textures woven into it. (https://www.moons.co.uk/product/oatmeal-4/) The cloth you chose for your B&Tailor jacket from Holland & Sherry is something I adore, but it gets discontinued either. I wonder if you may recommend similar cloth in this direction which can easily bridge the gap between formal and casual? Many thanks in advance!

Christoph

Hi Simon,

Just to make sure we are discussing the same cloth. I mean this one here: (https://www.permanentstyle.com/2018/02/btailor-jacket-via-robin-pettersson-review.html)

Any suggestions for a tweedy cloth in this direction?

Toby

Hi Christoph

Have a look at these two, lots of texture and tonal variation, Harris and Shetland respectively.

https://www.harrisons1863.com/product/24311ph/

https://www.harrisons1863.com/product/wb12402/

Christoph

Lovely to see. Thanks Toby!

Joseph

Simon , could I ask – when you speak of lapel width where/how do you measure?
From point to fold at right angles to fold, or, from point to fold straight in ie parallel to ground or from point to fold following stitch line that joins collar to lapel?
Its never clear, anywhere, just how people measure. And it does make a difference. Especially when speaking of small increments.

Chris

Hi, are you a cuff guy for all types of suits or do you have no cuff trousers as well?

Chris

Thanks, will check it out. Because cuffs are more casual, would you still wear them at for example, a wedding?

Chris

Great, thanks again Simon for your input.

Nicolas Strömbäck

Haha, this is spot on. It is amazing though how big a difference a half inch can make to the fit of a jacket. I recently picked up a SB baby camel sport coat by our friends @samanamel and even though the fit was good from the first fit, we tweaked it ever so slightly at the back and added some comfort there.
On the desire for comfort note. How much would you add to a formal business collar these days? Compared to the circumfence of your neck that is. I have noticed now with age that I increasingly dislike tightness around the neck (didnt bother me before) and was thinking of exanding my measurement with Luca. But how much can one add before it looks too loose?

Nicolas Strömbäck

Yes, and I am nowhere sliding anything in there. So maybe its time for that upgrade 🙂

Valery

Nice jacket Simon !
Question : now that things are going more and more casual, do you think you will still commission bespoke tailoring ? Or mostly casual garments from the new brands covered on PS ?
Since covid, most guys have ordered “tailored” safari jackets, but I am wondering what tailoring will become afterwards…

Manuel

Very interesting article. I understand most of your choices regarding style, but I don’t get the comfort argument. When you have to wear a tailored suit five days a week, and ten hours a day, than comfort may be important. But if you only wear tailored jackets for special occasions, why would you put comfort above elegance?

Steve B

I think we can have both comfort & elegance. Obviously much of this depends on your shape & how wells clothes sit on you, or whether you need the art of bespoke to deal with your shape. And possibly it is age & the passing of fashions & a desire to be comfortable in good clothes that make you happy & feel relaxed even if very smart in a suit – I experienced the worst of the 70’ fashion change so. The main point is keep fit, have good posture & be happy in what you wear. Neither better, nor worse, just you.

Manuel

Simon, Steve,
thank you for sharing your perspective. To me a curved silhouette, achieved by some suppression in the waist area, is still the most elegant one (if you have the physique for it). And I wouldn’t sacrifice this visual effect for more ease of movement. But that’s an aesthetic preference, and as such a sujective one. (I also struggle with wide trousers.)

Manuel

That agrument is convincing. But widening the shoulders isn’t an option with Neapolitan tailoring, is it?

Il Pennacchio

if the shoulders are widened, as they are here, then the waist can be let out the same amount and the relative suppression and shape is the same.

This is what Eric Jensen does to give my jackets shape in the waist.

Awesome article, Simon!

Charlie's Boy

The late great Charlie Watts of the Rolling Stones said he never changed his suit sizing and never had alterations done due to changes in his body (weight gain, etc.). Instead, he altered himself — ate less, exercised more, etc.

Charlie was our darling.

Steve B

Totally agree with this ethos. We spend a lot & time on our clothes & so we should with our body.

Micheal

First off let me say I love all that you do, educating us gents. I’ve bought multiple items from your site so I’m a fan.
However, I’ve always thought you would look better in a shorter jacket that’s more fitted. Then you do this article and I’m like man he looks so much better in that blue suit :). I guess it just becomes a matter of preference. I think the longer jackets just seem like an older look. I think we can agree Daniel Craig looks amazing in his suits and I would rather copy that look as far as cut. I think it is by far more flattering.
Nothing but love though Simon! I’ll be buying more of your brilliant pieces in the future. Cheers.

Andrew

Yes, that’s exactly right. Very clearly and precisely expressed.

Con

Just occurred to me what it also reminds me off as I’d forgotten i.e. during school years when everyone is growing fast and you go through growth spurts. Your uniform could need changing twice or even more during a year for some guys who really shoot up quick. Shirts become tight, the sleeves too short, eventually even trousers can no longer be left down etc. It’s uncomfortable, and that’s what I always think when I see these kind of fits, I feel for them, they must be so uncomfortable.

Micheal

I think it starts to be hard to find the balance between this more “relaxed”, flowing look of the fabric and an off the rack look. I know you and some readers here can tell the difference between the two in a second but I would say the average person walking on the street would not. I think we dress nice to make us happy and to build some confidence in ourselves but also to have an attractive look when we’re out and about. It’s a great feeling when someone complements you and can maybe tell you’ve put some thought and study into your attire.
But I put your pictures to the test to the ten ladies in my office and they all agreed they like you more in the blue suite 🙂 I know you’re not out trying to appeal to everyone but I think that says something. Maybe they/I have just been conditioned to like this look? Maybe it’s because we’re just not in tune or as knowledgeable about how a true bespoke suit/jacket should fit. That’s why I always look to you for answers!

Micheal

Excellent points as always. Thanks Simon!