Esquire ‘Five Fits’ feature: Tonal shirts and jackets

Wednesday, January 4th 2023
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Esquire magazine in the US recently profiled me for a column - their 'five fits' feature

It's run by Christopher Fenimore, who has been into menswear for about the same time as I have, although he was a little younger when he started.

It was fun talking about the early days of #menswear and what it felt like in New York - as opposed to London. The growth of Tumblr, particularly for Christopher and his street shots; the big deal that was the opening of The Armoury; the expansion of blogs and then explosion of social media. 

We conducted the shoot while I was in town for our New York pop-up, and the five outfits were a little limited by what I was able to fit in my suitcase; a couple of items repeat across them. 

However, there was one outfit I've particularly enjoyed in recent months that I'd never shown on PS, so I thought was worth featuring (below).

It's basically an extension of the tonal dressing we've discussed in the past - eg here for greys and cream, or here for brown and charcoal. 

But whereas those were quite smart, the tonal beige colours in the shirt and jacket here are  more casual. 

The shirt is a vintage US Army piece, and there are equivalents from many militaries in many vintage stores. The fit is blousy, but I'm fine with that in a casual shirt, and more importantly it has a wonderful texture - soft, worn, with the odd nick and scratch that speak of years of service. 

The jacket is my gun-club tweed from Ciard of course, and the fact it is a similar colour to the shirt pushes the combination I think towards the unusual and less traditional - certainly compared to that grey outfit in Paris

These tonal pairs are a fun area to play around with - grey shirt under grey jacket, black knit under black jacket, and of course navy under navy - without ever being over the top, given the colours are subdued and any pattern small enough to be barely more than texture. 

On the subject of vintage shirts, it's a category I was initially sceptical about - certainly compared to something like outerwear. 

But a few pieces have changed my mind - this army one, the red flannel featured here, and an off-white denim I picked up at Stock Vintage

There will always be compromises in fit, but if you have the body of the shirt altered then the compromises are normally limited to the collar (less of an issue if you never wear a tie) and sleeve length (only an issue under jackets, as I always roll my sleeves when there's nothing on top).

And in return you get something that has often worn in and slightly frayed, lending it an old-world elegance that many seek in a button-down oxford, or I love in my 12-year-old denim shirt from Al Bazar

You can read the full interview with Christopher on the Esquire website here

It's quite conversational, and easy to skim through, but covers several interesting topics. We reflect on the growth of menswear since it started becoming more popular, for example, and the idea I discussed with Ethan, that that market is maturing. 

Carl and Oliver embody a lot of that in what they make for Rubato, I think. And it's reflected in the list of things I give as menswear staples in that article, such as a really well-fitting, quality navy crewneck. 

The Rubato crewneck is a little higher at the back, so it works for everyone without a shirt. It has that V-shaped silhouette that they've moderated now and works really for everyone. And it's a lambswool that's strong and not precious. 

Anyone could wear it with a pair of old jeans at home or grey flannels to the office, and look more stylish both than the average Joe and the guy in a waistcoat and double monks that 15 years ago, I, Christopher and many others aspired to. 

Appreciating that is a real sign of maturing style, for me.

The other four outfits that Christopher shot had some nice angles, and I've reproduced some of them above and below. They should all be familiar to readers, but if any aren't just shout. 

Esquire interview here

Christopher is @c.fenimore

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Enjoyed this article, Simon, thanks. I’ve enjoyed a similar approach with various combinations including my jacket made with the PS Harris tweed worn over a chocolate coloured polo shirt. With the PS tweed, it’s even more interesting because the combination looks more tonal from a distance but then up close one notices all the variations in the tweed including the brown that’s picked up by the polo.

Peter Hall

Olive green shirts are a great base layer.

Do you think the market is maturing in response to the higher demands of its customer base ?

Peter Hall

Yes thanks. Once you get over the ground rush of realising many of the norms have gone, I’ve found it quite liberating and enjoyed the responsibility-if that’s the right word -of taking ownership of my own style.
I’m sitting in work,(black polo,cream shirt and black jeans) looking at the joggers and hoody brigade . Yes I am that man with the faded vans.


Nice article., though I think it could have benefited from a break-down of the outfits. I think the point about looking about the whole outfit can be made repeatedly, because it seems like the more one gets into #menswear, the easier it is to get stuck into tiny details, and sadly the community can be an echo chamber for that mentality. It’s not just about wanting the tan double monks, it’s about what leather sole thickness you should have for it (and what tannery is that sole from, and what GRADE OF LEATHER is it made of???)

Then we end up looking like Mr Bean. If we’re lucky.

I find it helps to try and look at myself in a full-length mirror, at a bit of distance, cause that’s how most people will see the outfit. The subtle difference in tone between the grey jacket and the grey-and-cream pocket square will go unnoticed at any distance, but the silhouette of the jacket, or how those silly tan shoes makes it look like my feet are cosplaying pumpkins, will be obvious.


Yeah, Ithink most regular readers recognise many of those pieces by now. Would be good for the esquire readers, in case any of them are interested, I think.


Hi Simon, great fits. Just a couple of points I wanted to make:

  1. The Ciardi gun-club tweed jacket is gorgeous. And I think the combination of cut and fabric makes it very versatile as a separate jacket. It’s a pity that the fabric is not available anymore. I was considering buying the tweed developed by JFK and the Anthology, and making it in a very similar cut with ciardi. Do you think it is as versatile, more, less? Also, about the cut, I’ve noticed Ciardi house style as a quite high notch, but yours seems to be high but slightly lower than their deafault. Is it? Or it is the default? In this jacket I think it looks good, and it’s the thing I like less in Ciardi, which is my favourite style out of the all the neapolitans covered on PS.
  2. The DB cordoroy is the best casual DB I’ve ever seen, absolutely love it.
  3. I love the brown tonal look with rubato V-neck. It’s so well put together. And it’s very interesting how one accessory makes a huge diference in smartness. The look with the baseball cap gives a much more casual vibe, and the one with glasses a much smarter one.
  4. Related to number 3. This is a very specific point but I think a lot of fellow readers, and maybe yourself, will relate: Is there anything better in life than contemplanting the drapping ripples of a great quality fabric (as seen in the V-neck and often on trousers)? Maybe… But very few…

Simon, I’ve noticed you nearly always show your Rubato earth v-neck with a white shirt. Is that because the images are often the ‘brown on brown’ look or have you found it difficult with other colours?


Which shoes are you wearing in the top picture? (The calf leather loafers)


Great article. Where’s the wallet from? Thanks


Simon, it hurts me to be honest but I personally do not like the way the beige shirt works with the gun club jacket. The shirt on its own with the trousers, would look great but the color of the shirt with the jacket makes it look like the type of character who would wear a yellow dress shirt. Apologies for my honest thoughts. I have a lovely cream colored oxford shirt that I personally have a hard time pairing with. Those types of colors with tailoring can look a bit off….


I find yellow very hard to wear in general.

In a Checked jacket I have, there are brown yellow/mustard tones aside from Red and Dark Brown. The Jacket in itself is lovely, but I always feel like a 70s caricature just because it is so mustardy.

Same with a yellow cashmere jumper, it is more of a lemon sorbet colour but still, would be much nicer in any other colour.


I tend to agree here. I like tonal combinations but I think they work best when most of the pieces are in subdued shades. Here I find the shirt to be too strong a colour. If it were a bit paler or a muted darker colour like a faded olive green it would work better to my eye. But as always I enjoy seeing how Simon puts together outfits like this because even the ones that are not quite to my taste give me ideas for how I might put together a slightly different outfit.

Peter Hall

As a regular wear of yellow(and pink and lavender) I think it’s vital you get a shade which matches your skin tone. I really like the yellow/faded to cream shade but I would happily wear a stronger yellow with black .


Completely agree with you on that Peter. I have a slightly yellowish / jaundiced skin tone and find that yellow generally does not flatter me at all, so I avoid it.


I love yellow, but for years avoided wearing it as it thought didn’t flatter. But with age I cared less, and wore as I love the colour – a yellow Shetland from Trunk and yellow wool polo from Connolly.

With both, strangely I find I enjoy wearing them so much it actually works. The shade does obviously matter though, and a pop of white underneath helps (vest or shirt)


Details on your belts pls. They look nice.

Andrew Eckhardt

Quite a nice conversation in Esquire! Your mention of essential brown suede boots in the piece caught my attention, as I’m having a bit of a boot crisis at the moment. Would you, Simon, or you, readers be kind enough to share some thoughts? For a decade I had a fairly casual black and brown boot with a brick red wedge sole that I wore during the cooler months in Minnesota when I didn’t need to break out the Sorels. Regrettably, they were recently destroyed during recrafting, and I’d like to replace them.
It looks like brown suede boots would be appropriate to wear with grey flannel trousers or indigo denim? Simon, I rooted through the site and found you sporting an Edward Green Cranleigh, I think. Thoughts on that make and model? Any alternatives I ought to consider? I prefer wedge soles, as I work in engineering and appreciate the comfort for my arthritic toes. But perhaps I should consider a Dainite or alternative Vibram sole? Many thanks for your thoughtful articles and input.

Peter Hall


I have a pair of dark brown suede boots by Tods which I am very happy with and go with just about everything .Similar price point to Crocketts.

I had to have them resoled(2/12 years), but,I was wearing them 3 days out of 5.


Thanks for the recommendation, Peter. Being rather unfamiliar with the brand, I looked over the offerings in Tod’s web shop. Much of their sole selection appears to be trending towards the fanciful! Perhaps this is a recent trend?

Peter Hall

I’ve had mine a few years.This is the version of mine

I agree about some of the current styling.

Peter Hall

Sorry! Wrong linkcomment image&


Many thanks, Peter. Looks like a very smart chukka. Now I’m wondering if maybe that’s a style I ought to pursue. I’ve an unlined version from AE that I love wearing in the summer, maybe a version for cooler weather would be nice.


Appreciated, Simon. I’m thinking about replacing my destroyed AEs with a smarter pair and a more casual pair, and it would be lovely to get an EG to wear with flannels. I snooped a little more and see you might also own a pair of EG Galways? May I trouble you for your thoughts on the Cranleigh’s apron versus the Galway’s cap toe (or any other appreciable differences)? Also, any insight into C&J’s use of a half leather lining with a waterproof membrane interlining in some of their boot collection? Seems like something that might break down long before the rest of the boot, but I don’t know much about it.

Peter Hall

Andrew ,I have worn my C and J Chelsea boots (no 11) in three dutch winters and have dry feet. They are leather grain and have a vibram sole.
Once I had a slight dampness of sock, but I was cycling in a true winter storm. The only thing I have found is that there can be a slight gap at the top which is the downside of no laces. In really poor weather I wear work boots with the C and Js in the rucksack .


Great article Simon. Just a general thought on knitwear that i have on my mind (and i will try to express it). From some of your previous articles, i felt that knitwear was the least important category to think about (as depicted on articles on massimo and uniqlo). As trying different quality and fits myself, i realized that it makes a huge difference at the end.. e.g after wearing a Rubato, the massimo knitwear looks bad. I also like the way you wear your knitwear, a bit roomier fit. When does the fit start becoming sloppy in your opinion? i still try to analyze too much maybe 🙂 by focusing on tailoring, shirts and trousers, i never paid attention to knitwear (with some bad spontaneous purchases).


Prince Florizel of Bohemia

Very interesting ideas! I’m particularly taken aback by the outfit featuring DB jacket. I didn’t imagine that corduroy jacket in that color would work so well with a black belt. Just a little note on the Five Fits interview. As a music professional, I cannot stop myself form pointing out that tempo rubato has been used in classical music long before jazz was born, particularly in 19th century romantic music. Traditionally, most music markings were in Italian, hence the Italian phrase. 

Prince Florizel of Bohemia

Thank you. Interesting! Perhaps it’s my screen, but in this post, the cord jacket looks oatmeal/beige with dark brown buttons, whereas pictures in the older post you are referring to, cold grey with black buttons. 


Wow, so that’s the Ciardi DB? Really looks like two different jackets. Beautiful. Do you happen to know the fabric bunch?

William Kazak

Why do you roll your sleeves when not wearing a jacket? I have seen pictures of Gene Kelly wearing long sleeved shirts rolled up over his elbows. I don’t understand wearing a long sleeved shirt rolled up. The only answer I can come up with would be to purchase only long sleeved shirts to save money and closet space. Please explain.


At school (in the UK) we had ‘summer uniform’, if temperatures got too hot for our really heavy jackets, which essentially meant trousers and shirts. In those instances we were required to roll our shirt sleeves up. I always just assumed that it rule of dressing, however never really delved into why. I believe the same rule applies in the army.


There’s a whole bunch of stuff about clothing as a whole that I find really depressing. There are so many brands that are really hype-driven, which is sad. I actually see a bit more of that in New York, where their presence is more obvious, whether it’s Supreme or Kith, or all these kinds of brands. I find it depressing because there are so many people who really want these products but they don’t really like the product itself very much. They don’t like the clothing. They like the idea of it and they like the idea of possessing it. I don’t think those two things are really particularly healthy. I remember someone saying in a comment to me on the website that I thought people were be bit too materialistic, but I think that’s actually wrong. There’s too much consumerism. There should be more materialism because materialism is caring about things and materials

Never a truer word spoken. I made the mistake of going to Selfridges last week, everything (and everyone) just looked cheap. Depressing is right.


Mr Crompton
Like Wednesday I do not see a new Friday article posting today.
I think you may want to know.


Always enjoy the gun club check ( will we ever see the fabric on offer as a collaboration? ) and the dove grey db corduroy (never reviewed ). The 3rd and last pics are reminders of why I avoid plackets. The military shirt without placket is clean and crisp. Plackets always seem unkept especially with thicker oxford cloth. This is universal to all body types so I try to avoid when possible.


Sorry I must have had a “senior moment” as today is Thursday not Friday.

Seán McGrady

Splendid read my dear chap!


Simon, how wearable do you find the black alden loafers in the first image? Would the color 8 have been a more versatile color?


So it is! It really is the most fantastic color. I have been searching for the same shoe and, whilst I have found it in black cordovan (via Gabucci) I haven’t been able to find it in color 8. The search continues….


What are the trousers that you’re wearing with the gun club jacket, please?


Enjoyed your article, thanks as always. I was particularly interested in your comments about the maturing that’s been happening in recent years – post the menswear ‘bloom’ – it’s something I have noticed in your approach recently, when I think back to your earlier writings (from when I first started to follow the blog) and my own response to them. Inevitably some of that change has been a response to the work environment and the ups and downs of the western economy but some of it, it seems to me, is simply life-stage or the ageing process – fashion Vs confident dressing from a mature understanding of what’s expected and how well you want to fit in Vs what’s left in the bank account at the end of the month!

Chris L

Enjoyed reading the interview! As someone who attended your first NYC pop up I was curious as to how you go about inviting different brands to join you. I know you mentioned that you invite some brands that you’d like more people to be exposed to, which I think is really cool, but I am curious if you ever thought of having a poll to ask your readers who they’d like to come with you. Particularly, I would personally be interested in seeing Blackhorse Lane next year in NYC if you decide to come again.


Great article. I’m a huge admirer of your work, and the comments on consumerism are insightful. I do think the remarks on shoes are a little misguided. Traditional men’s shoes prioritize style over comfort and healthy biomechanics, coming from an aristocratic lineage of pointed shapes that were not well designed for work or walking (not to mention the animal abuse and toxic chemicals of leather production). Sure, at the high end, bespoke can be more comfortable than a department store dress shoe but the fundamental unhealthy design problems remain. Healthy shoes would be foot shaped, low heel drop, and low to the ground but we’re now stuck with an aesthetic heritage that restricts our natural toe and arch movement causing structural problems as we age. I don’t blame people for shifting to ugly comfort shoes. If only there were better looking options.


Great interview in the Esquire magazine. Congratulations.
One comment: Contrary to all other combinations you show in the Esquire, which I really like, I find the gunclub jacket combination not good. I guess it is not really the combination of clothes you wear. It is more the jacket by itself. I find square-patterned jackets look restless to the eye, are difficult to combine, look somewhat outdated / old-fashioned and (not with your jacket) are in danger of bordering somewhat on a clownesque look. They always remind me of my father coming home from his office in the early 90s, not the best period for style in general (moustaches, horrible wallpaper, poor architecture).


That Esquire interview was terrific! So personal and yet for that reason of universal usefulness in terms of the counsel and sensibility.


Excuse me if I simply missed it, but I dont see it mentioned anywhere. The off white trousers you are wearing with the gunclub jacket, where are they from?

David Schnabel

Thank you for sharing the Esquire article. As for New York men wearing great clothes with comfortable but ugly shoes, comfort drives that, as you observe. We New Yorkers walk far, wide, and often. The pavement can be quite hard on footwear, hence affordable comfort over expensive style in most cases. But as you say, a balance can and should be found.


The sidewalks in New York are far more treacherous than Paris’, I’d wager. Here each home owner is responsible for their own patch, so the pavement is incredibly uneven. My poor shoes.

Gary Mitchell

I see your Paris and raise you a Maputo pavement… Think ploughed field with broken concrete. Shoe killers

robert e gault

In a piece such as this my first response is….”What no fedora?”…but then I do have a distinct bias.


The second image–the gun club tweed and the vintage army shirt–is one of my favorite combinations you have posted over the past several years.
I’m not entirely sure why however. The looseness of the shirt perhaps? Is it a more “dangerous” look as you have more freedom of movement? Or is it that it might remind me of vintage Ralph Lauren ads from the ’90’s, where, let us be honest, everything was blousy.
In any case, it’s great!


Interestingly, Rubato is very important in romantic music and often indicated in Chopin’s sheets. To designate a segment of the piece wherr the player is allowed to use whichever tempo he wants – « stolen » from the one attached to the piece.


Good afternoon from new york… always a good article..what caught my attention was the picture of you wearing a beret..BRAVO!!!!! I wear berets in various it popular in the U.K. and various parts of Europe???? In the states…. No….


I’m somebody who wears loafers a lot because I remove my shoes often during the day and I’m too lazy to tie shoe laces.
But I think loafers don’t look very natural in combination with thick overcoats. Whenever I wear an overcoat I put in the effort to tie shoe laces. But this winter I needed an overcoat maybe only two or three times. Other than that a Jacket was warm enough.


Hi Simon, regarding the beret you’re wearing with the Donegal coat: it looks similar to Tony Sylvester’s ‘short flight’ berets, but without the, er, thingy on top? Is it in fact a different kind of beret or did you just snip the stalk off? Because I really like your version.


Aha, thanks. In that case the AWMS beret is still the one I’ll be buying.