Five paradigms of casual clothing: Which do you wear?

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Although casual clothing is far more susceptible to fashions than tailored clothing, it is possible to organize it into certain groups, or paradigms.

These groups, such as preppy clothing or workwear, often have their roots in particular parts of the world or periods of history - but such is the variety of brands today that they are all effectively on offer.

I would suggest that it is worth the reader keeping these paradigms in mind when deciding what casual clothing to buy into.

Because while many of them overlap, each has its own aesthetic – in terms of cut, texture and colour – and this can make them hard to mix together.

An Italian lambskin-leather jacket may look too polished and smooth to mix with rough, broad-legged cargo pants - slim, sharp chinos might be better. And the cargo pants could better suit a battered old horsehide jacket.

Below I’ve suggested five rough paradigms of modern casual clothing.

They come with a lot of caveats. Each overlaps with the other to some extent. Each has splinter groups that could be subsumed or split off, depending on your definitions. Each has sub-groups that are often easier to define (polo, motorbikes, Mods).

They pretty much all derive from sport or war.

But I do think this division is a good starting point, as a way for men to start working out why that Canali blouson doesn’t work with those Cabourn jeans, or on the flip side, why a Shetland sweater is a natural match for corduroy trousers.

As ever, interested to hear everyone’s views.


Paradigm 1: British country

Images: Drake's, Cordings and Barbour

The style of the British landed gentry has arguably been the dominant force in western menswear since the ‘great renunciation’ of the late 18th century. And it's certainly influenced hundreds of brands and designers, particularly in the US.

This is elegant clothing, often tailored, but in cloths suited to country pursuits. Greens and browns with pops of bright colour; traditional waterproofing techniques and lots of emphasis on texture.

Primary clothing: Tweed, corduroy or moleskin trousers, waxed jackets, checked jackets and tattersall shirts, pops of colour, suede footwear, and decoration with pictures of animals.

Secondary clothing: Cardigans, fisherman’s sweaters, covert coats, wellingtons or riding boots, flat caps, quilted jackets, Shetland sweaters, and tweed suits or hunting jackets (bellows pockets, bi-swing back, poacher's pocket).

Sample brands: Drake’s, Cordings, Barbour


Paradigm 2: American prep

Images: Ralph Lauren, J Press and Tommy Hilfiger

In many ways, American preppy clothing is a re-working of English country clothing, with clothing such as bright trousers and tweed jackets in common.

But such has been the growth of American fashion over the past 50 years that brands such as Ralph Lauren and Tommy Hilfiger have made some of these items their own. And the way they are worn (often involving more sports, and in a more urban context) is also quite distinct.

Primary clothing: Oxford button-down shirts, boat shoes, club ties, varsity jackets and polo shirts, cordovan and saddle shoes, and madras made into anything.

Secondary clothing: Seersucker, shorts with embroidered symbols, cable-knit jumpers, ropes or ties used as belts, the baseball cap and polo coat, white ducks, bow ties, boating blazers and horizontal-stripe knit ties, the navy blazer and go-to-hell brightly coloured trousers

Sample brands: Ralph Lauren, Tommy Hilfiger, J Press


Paradigm 3: Italian smooth

Images: Zegna Couture, Corneliani, Ermenegildo Zegna

It’s often striking, given their number, how similar most Italian menswear brands are.

Without the label you’d be hard pressed to say whether a grey-cashmere sweater with brown-suede details was Brioni, Corneliani or Cucinelli.

They do vary, of course, but there is a definite Italian aesthetic in casual clothing. It can be characterized as simple pieces in muted colours (particularly navy and grey), in sharp, clean cuts and often soft, luxurious materials.

The simple, chic aesthetic is also to an extent Scandinavian and French; but the Italians dominate.

Primary clothing: Cashmere sweaters, loafers, white trousers, rollnecks, smooth leather jackets and brown suede. 

Secondary clothing: Half-zip sweaters, perhaps worn over the shoulders, chinos, exotic leathers, micro-fibre waterproofs, shirts undone one button more than usual. And bare ankles

Sample brands: Zegna, Brunello Cucinelli, Canali


Paradigm 4: Workwear

Images: RRL, Nigel Cabourn, Filson

Functionality without those associations with the upper classes. Working the cattle and working the railroads. Tough, practical clothing where style is a coincidence.

A heavy influence from military clothing and from everyday pursuits: leather flight jackets to neckerchiefs to duck boots.

This is a broad category, but its materials and cuts are largely distinct. Lots more cotton (particularly denim and canvas) and leather; bigger, higher or shorter cuts to aid the practicalities of use.

Primary clothing: Jeans and denim jackets, khakis and leather jackets, checked shirts, waxed boots and T-shirts

Secondary clothing: Overalls and cargo pants, neckerchiefs and watch caps, elements of old sportswear like baseball caps and sweatshirts

Sample brands: Nigel Cabourn, Filson, Levi’s



Paradigm 5: Sportswear 

This is clearly the fifth paradigm. It has probably had the biggest influence of all five over the past 50 years, from the dominance of the trainer/sneaker to modern athleisure. 

However, it is not an area we cover much, so I’ll leave it without definition or explication.


There are many things these groups leave out and many they subsume.

All overlap: 1 and 2 share club ties and tweed; 2 and 3 share loafers and sweaters-over-the shoulders; 4 and 1 share quilted jackets and flat caps.  

Brands overlap too. Although Drake’s is perhaps mostly defined by English country, it also indigo scarves and Italian polo shirts.  

But separating them is useful. It’s the reason I usually wear my Chapal flight jacket with my Armoury chinos, but my Valstar suede jacket with Incotex chinos. Each pair is cut with the same look in mind.

So when a reader asks whether he should buy Chapal or Valstar, my response is not normally about quality or price – it’s about style.

They can all be mixed and mixed well; but as with any area of menswear, it’s best to master the classic, established combinations, before moving on.

Which do you wear most - and which do you mix?

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Great write up. Thank you. I find that for fall/winter I lean more towards the “British country” look. And for spring/summer I tend to mix in more Italian style clothing, with loafers and linen.


Do you honestly think that British country clothing brands cannot cater for spring and summer? Cordings linen tweed jackets are excellent. Oliver Brown’s linen jeans and shorts are superb. For spring time, both stores sell twill jeans and drill cotton trousers in a huge range of colours. All made in the UK at a reasonable price.


Couldn’t agree more Rikard and I was just thinking exactly the same thing while reading through this article. My own style, especially these days, is very ‘British country’ in the Autumn/Winter, but it’s near-impossible to maintain that through the warmer months.

Without trying to sound snobbish or superior – general standards of style drop to subterranean levels during the summer months here in the UK! That Italian aesthetic is a great (and practical) style to adopt in warmer weather.

Richard W

Intriguing as always. But … isn’t choice of casual clothing more about affiliation to a current “tribe” (i.e., your mates, your family) rather than being concerned about historical “correctness”? Of course the result may be the same but more likely it is not.

Richard W

Maybe overthinking this a little, but it’s still interesting that in previous posts you define formality in terms of patterns/texture/colour etc., i.e. “a-historically”, whereas with casual clothing there are, in addition, these various historical templates to choose from. Which in a way implies that casual clothing is more difficult to get right than formal clothing.


I’ve always thought of myself as more prep, though much of what I wear on a daily basis as a student—shetland and donegal sweaters, a barbour beaufort, occasionally corduroy pants— you’ve filed under English Country. I wonder if this is simply a fact that I come from the other side of the Atlantic than you. Though shirt wise, I almost exclusively wear polos and OCBDs . Speaks well to the point you made about the mixing between paradigms.

Simon C (not Crompton)

Great article Simon. If only the British weather would behave enabling you to wear Italian casual in the morning and not get your Tods loafers wet through in the afternoon!


Really nice post.

I’m not necessarily disagreeing, but one thing I’ve always liked about the Drake’s aesthetic is that it’s not interested in creating the illusion that your family owns half of Derbyshire (cf. the other two photos in that section). In fact, things like Drake’s knitwear and jeans have workwear roots too.

I wonder if there’s not another interesting distinction between urban workwear (denim, work boots, factory clothing, etc.) and rural workwear (fisherman’s sweaters and the like).


Interesting article. As in a previous comment, I favour English country/Ivy/Workwear in winter and Italian in summer; right clothes for right weather conditions.


A really useful piece and I can now trace the origin of some unwise and under utilised purchases. I’d also offer the trend toward outdoor clothing as an influence. It’s not workwear or sports but many brands have an offering that has a distinct walking or mountaineering influence.


Its certainly an interesting idea but it does make me wonder if its really down to the family/paradigm/history or more at the core is the topics of formality and colour and the paradigms are naturally a grouping of these?

Personally I struggle more with casual wear much more than formal. I like english country but it feels wrong when I spend 99% of my time in London, NYC etc. Formal end of preppy and italian doesnt match my circle and the informal end doesnt like me or I don’t like it.

Most the time end up with jeans (501), oxford button down or t’shirt and light weight cotton or merino jumper with anything from roughout chelsea boots, smart trainers or suede shoes which probably is in one of those overlapping areas (or just poorly coordinated)


Aren`t chinos quintessentially ivy league?


Not particularly helpful frankly.

Why would you want to lean towards a workwear “look” unless you were going to…… wearing it.

If you are Italian, or Spanish, or French (to a lesser extent) you will embrace the English “country” look in cooler weather. And from those countries the “preppy” look will come more from Hackett than RL.

And why wear Sporty stuff………..unless you are off for a spot of sport.

All in all, pretty meaningless.

Don Ferrando

Simon, there is always one “anonymous” who is very critical to everything you write in this blog.
Is this always the same person ( looking at his IP)?
If so, it would be helpful if this person would choose a nickname.

Kev Fidler

This is a very interesting and useful thought process to go through; I can identify with each one according to what I’m doing. The key to it I think is dress appropriately; just today I am out photographing in the snow so have outdoor sport type clothing. Tonight is a casual social event so will change into something appropriate. The danger with these groupings is to identify too closely and it becomes a sort of uniform – tweed jacket, therefore a checked shirt and tie with pheasants on. I get the point about difficulties mixing styles but what about the excellent outfits on this site, Simon? Thinking of tweed or wool jacket, button down shirt and chino combinations as a mixture of three? It’s useful to be aware of paradigms but surely your article from some time ago about dressing around one item (How to get dressed in the Morning or something like that) is actually more useful?


I see a great part of my wardrobe in those categories, indeed i usually dress in more informal way (3-to-7 in your scale).

I usually wear:
– in fall winter tweed sport coat with cord or flannel trousers, cashmere knitwear, jeans and denim shirts
– in spring summer seersucker shirts, polos, shorts…so a little preppier and a lot of linen garments (suits, sport coats, trousers …)

Maybe never in the fifth category.


I think this topic is one of the most interesting you cover.

During the week my wardrobe consists of bespoke suits, overcoats and fine shoes yet at the weekend I am very casual; I love trainers and relaxed brands with minimal aesthetics like Acne, APC and Common Projects.

Equally important to remember your surroundings – I love the Drake’s look, but in reality, these weekend looks are difficult to master without sticking out – when was the last time you saw someone wearing a club tie and tweed jacket on a Sunday in the pub (inside the M25 that is) who didn’t look affected?

The key for me is mastering and striking the balance between formal and casual and drawing inspiration from both to put together an outfit. Too far in either direction and you run the risk of feeling uncomfortable, which is the opposite of what clothes are meant for.


Ultimately these type of segmentations fail because they take no account of age, location or leisure pursuits.
I spend a lot of time in the English countryside but anybody arriving for a shoot dressed like the party in the Cording’s visual would provoke a belly laugh that would be heard from John O’groats to Landsend.
The last time I saw somebody dressed in this fashion they proved incapable of hitting a barn door at ten paces.
In terms of my own style, although I probably buy a good 50% of my casual wardrobe from A&S Haberdashery it is heavily supplemented by heritage pieces that I have owned for a very long time and probably the closest visual interpretation would be the Drake’s aesthetic.


Interested to hear your thoughts on the below comments on this. Not sure if lots agree with looking silly!


I would strongly disagree. I wear my tweed shooting suit, schoffel and cap most days in the field (as do most I know), whether it be walked up or double gunning.


Spot on! A tweed suit is expected if you are invited to a shoot on a top estate. If you go to a livestock market in Yorkshire, most of the farmers are wearing tweed suits and wellies. For many country people, tweed suits are smart, practical and warm workwear rather than a county “aesthetic” or “paradigm”.


I’ll second that, and not just for shoots, deer stalking, game fairs and country shows but as practical and warm day wear. Most estates around me (in Scotland) have their own estate tweed and you’d be insulting your host if you showed up to a shoot in lesser attire than the gamekeepers, ghillies and beaters. A tweed suit or at least hacking jacket is almost de rigueur for Sunday lunch, land agents, insurance brokers, and farmers at the “mart”.

JJ Katz

I think that, with all the caveats Mr Crompton pointed out, this is a useful concept.
One might add the whole retro/vintage side of things but that’s more an approach than a strictly casual style.
What I find, personally, is that (perhaps due to transatlantic life experience) a slightly Briti preppy look comes quite naturally and effortlessly.


Another factor to throw into the mix – the American prep look has apparently changed over the years due to the influence of black and rap culture.

Peter K

Workwear for me in the winter with elements of English country. A toned down American prep (polo shirts but solid coloured shorts) in the summer.

Juan Antonio Rodríguez Ortega

Definetly I’m an advocate of british country style and beyond that, english style itself. The reason is simple, the majority of the key pieces in a man’s wardrobe have their origins in England and moreover, I’ve been always attracted by their rural aesthetic and military heritage . Items such as a duffle coat, a trench coat or a waxed jacket are timeless because of their design and functionality. I believe that you can easily develop your own style framed within these iconic garments. It is a pleasure to read you Simon, all the best.


So no French chic paradigm ? 😉 ^^


Great topic. In FW I’m generally in English country style for work and workwear for casual wear. In SS I tend toward Italian smooth for work and American prep for casual wear. Sportswear is only worn to the gym and maybe coffee on Saturday morning.


Great article Simon. I suppose lots of people have two distinct ways of dressing (suits in the week, workweary stuff at the weekend) but a really stylish guy is able to draw from multiple traditions, sometimes at the same time, and make it all feel coherent and subtle in ways that blur the the formal/casual lines. (Like an Ethan Newton.)
Drakes latest lookbook offers an interesting case study in that sense too. Preppy and ivy, (and literally photographed in South Carolina,) without feeling like a total deviation from their usual vibe: the imagined ‘Drakes Man’ exhibiting exactly that kind of subtle and (to my eye,) successful, ‘tradition hopping.’


A good article Simon. Personally I mix styles up. In Autumn/Winter I wear footwear by Trickers logger boots, Red Wings Merchant boots, Churchs Goodward Chelsea boots. Pants are LVC 1947 501s. Oxford button down shirts by Gitman Vintage. Jumpers by Brora in French navy. Buzz Rickson sweatshirts in grey or navy. Buzz Rickson Navy CPO shirt. Coats/jackets by The Real McCoys M65 jacket, Woolrich pea coat or classic parka, Gloverall navy duffle coat.

In summer I wear footwear by Doek basket shoes, Quoddy boat shoes and loafers, Church’s desert boots. Gitman Vintage shirts in linen, madras, and light cotton. All long sleeved. Brora cashmere crew neck jumpers and Buzz Rickson sweatshirts. Pants are LVC 1947 501s and The Real McCoy chinos. Jackets by Baracuta navy G9, The Real McCoys denim jacket and M65 jacket. All socks in navy blue by Falke.


Simon I’d love to hear more about some of the other paradigms that are often glossed over. Streetwear, Scandinavian (which I personally see as quite distinct from Italian style), African, Native, and Asian influences are notably absent here.

To wit, madras patterns used in ‘preppy’ wear have deep roots in Indian clothing, and the drape of Italian clothing has even cited South Asian influences as recently as Eidos collections. Subcultures often have more impact on the way we dress than their originators, see Japanese interpretations of Ivy style and workwear as recent examples.

In writing this I would note that there are many paradigms/influences that we borrow from, some receiving more credit than others (for a host of reasons I wish would also receive more ink), but the beauty of today’s menswear resurgence is that people have blended these looks to create a varied and egalitarian approach to fashion depending on their mood and the day of the week.

This post is a good start, please explore this idea further.


An interesting set of paradigms. From an almost anthropological perspective I do wonder if these typologies are more subjective than they might be in the formal arena. Eg discussing with my 16 year old nephew I could explain differences between english structured and naples unstructured and he’d no doubt agree. But he woul probably consider most of these categories “vintage” and divvy his usual stuff into something like 1. comfort/lounge/athleisure, 2. stylised urban/hip-hop, 3. rocker, 4. Smart casual, 5. Vintage


A very interesting (and somewhat brave!) attempt to classify the myriad genres of casual clothing. I do see what you mean about sticking with established combinations, but I think I’m with other readers who point out that some of the most interesting casual looks are where multiple genres are successfully merged. I think going “all in” with one style can look risk a bit contrived or even constumey. To my mind, what makes Drakes so interesting is the way they merge traditional British pieces like tweed jackets with more “Italian smooth” items like pale chinos for a much more modern look. By contrast, a more “consistent” look with cords, tattershal shirt, flat cap and wax jacket, might be more correct but also might look a bit old fashioned and fussy on a younger man. Some of my favorite casual combinations on PS also seem to crossover in this way; like your vintage field jacket and watch cap over flannels; or tweed overcoat over a cotton hoodie and trainers; even the infamous jacket and jeans!


“However, it is not an area we cover much, so I’ll leave it without definition or explication.”

What about the modern take on sportswear from brands such as stoffa. If I’m not mistaken they even refer on their website to their trousers as “sports trouser”. To me their aesthetic references 1920’s sportswear (I’m thinking along tennis lines) and does so with a modern twist.


Such a great post. I am mostly wearing English country and preppy stuff and is wonderful how some pieces of these can be combined very successfully with tailoring.


These are certainly some of the most common aesthetics but let’s best not be parochial. Even if we limit ourselves to the developed West, consider Saint Laurent’s metrosexual rocker (moto jackets and skinny jeans), silk shirts and espadrilles in Miami, urban ninja stuff from Japan, tailored dashikis and thobes, and whatever it is that Thom Browne did to us.


Not sure whether this is a general experience, but I find it interesting how I’ve ventured pretty hard into many of these categories as my interest in menswear has evolved.
Starting out somewhere in the preppy universe, naturally venturing into the British country look which in turn turned me into ‘stile inglese’ which lead to more lux casual Italian style.

Living in Sweden the British elements are naturally the most practical considering the climate, however our closeness to the water and light in the summer also allows for preppy and Italian influences.

While it can certainly be costumye too, I believe the Italian look is the most forgiving one to venture into without looking like a caricature.


Very useful, context-wise, Simon, thank you. During the workday, I myself wear a mixture between American Prep and English influence, usually with traditional SB overcoats, mixing it up with a Peacoat sometimes; in the evenings and weekends, workwear-influenced clothes. I also enjoy wearing a hoodie and runners with my more formal overcoats on weekends, or a conversely a beanie with overcoat and suit on the way to work. I can see where I might need to invest is in more tailored items for summer.


It’s an interesting, thought provoking little article. I liked it a lot. The categorisation i found interesting and useful. I suppose work wear for those not wearing it for work, but for fashion is rather post – modern. British country clothes are more acceptable worn outside Britain in cities, as there aren’t the same class associations and judgements. Italian chic is chic where. I will echo the question of another here, what about France? French country style is similar to British country style, though slightly different. Perhaps, that’s a question for volume 2. Great article.


Very helpful actually. I can get dressed in about 15 minutes if going to court. I don’t get stuck on whether to wear a grey or blue suit. If confronting the need to be casual, I just stand staring into the closet for extended periods.

Peter B

Great article Simon.
I would just replace “american prep” with Ivy Look or Ivy Style. And mention that its origins are an anglo-italian sensibility thus the perceived twist on English country but softer. And “preppy” is a subset of that with basically brighter colours.
Although maybe delving in like this isn’t so important for the overview.


Nice detail


Thank you, Simon, for your article it is very interesting.
I wear mostly British country and American prep with some items from workwear.

Take care



Great article and, it would seem, thought provoking for many. Rather than ‘paradigm’ I think five ‘influences’ might have greater accuracy. As a paradigm is a model keeping solely to its influence invites critique on the basis of uniform safety or, at worse, costumery. I think the list is missing two of the most important influencers though; the military influence, especially in urban wear (boots, camo, M65, bomber etc.) and music (jazz, zoot suit, teddy, rock, rock-a-billy, metal and currently the most influential hip hop). Due to army surplus military wear has a constant presence and influence. Everything from sweat-shirts, chinos and field jackets through to ammo-boots, parkas and trench coats find their roots in the military. Over the last century it has certainly been the largest contributor of new designs for everyday wear. Possibly the greatest reportage of international trends is ‘the sartorialist’ site and at its heart is the blending, mixing and re-interpretation of influences from all of these groups. This aspect of blended influence has been displayed on PS (hoodie, watch cap ec.) and forms the individual, idiosynchratic and sometimes eccentric basis of the ‘street wear’ or casual look internationally.


Very interesting points! I still can’t decide if I would consider “music” a whole separate category of influence (in the way that military and sports are.) It’s certainly true that music subcultures have defined and popularized distinct clothing styles, but I can’t think of many items of clothing made specifically for that type of music. Leather jackets are an iconic rockstar look, but have their own workwear origins outside of the musicians that adopted it. Similarly many pieces that define hip-hop clothing look are themselves rooted in sportswear.

Zoot suits though, I really can’t think of any other explanation…


I’d say I fall in the prep category, though I’d rather name it trad. Prep to me is in it’s core a weekend version of trad/ivy that’s been turned it to a faux lifstyle image of clever marketing people to sell loud and ugly clothes.
I live in tan chinos and oxford button downs in either white, blue oder blue white striped. During Fall/Winter I’ll throw in some tan cords and grey flannel trousers. When it’s cold I layer with shetland or aran sweaters. When the ocasion calls for it a navy blazer.
For shoes it’s boat shoes, tassel or penny loafers.
Outerwear is mostly a Barbour Beaufort or a navy Duffle coat.
Though probably not very high igent fashion I find that with these items one can be well dressed on both sides of the atlantic without beeing overdressed nor underdressed in most everyday locations, and still be very comfortable.


Simon, I just wanted to say that even though casual or semi casual subjects like this one is not the core of PS, I find I enjoy those segments and posts the most. For me personally it’s mainly due to them being closer to my own day to day life.
Judging by the comments this rings true to many, being well dressed in a casual matter is a lot harder than looking good in a suit and tie.
Keep ‘em coming.


Outstanding article. However, no mention has been made of the hipster look where the hipster objective is to spend a lot of money in clothing but in such a way as to give the opposite impression i.e. make it look as though their clothing is inexpensive.


Thought provoking article.

I would personally would rearrange the classification to
a.) collapse sloane/eurotrash/prep into generic a “landed gentry”,
b.) add a militaria, including all design element from formal wear of military origin, and
c.) keep sportwears and workwear.

I would further assign a points system, 1 mark for each of the above elements
– 1 points You are in a costume
– 2 points Standard
– 3 points Interesting
– 4 points You are trying too hard.


This is a brilliant article, Simon, most enlightening! Thank you for writing it.


I also dress more “Trad” than “Preppy,” which I think is a more fitting label (or approach, I should say) for someone who’s a little older and/or isn’t attempting a bright or youthful look. Same as Anonymous above – chinos and button downs and loafers are the foundation of the look, but I might wear one of those heavy English jackets, or something workwear, or something light and Italian on top. Maybe I’m quibbling over a term but I think a self-identified “Prep” has a much narrower (and more bright or loud) range than a “Trad.”


Nice article.
Don’t necessarily agree with sportswear been the biggest paradigm, would certainly say it is the fastest growing.
(Particularly with the relaxation of what is now acceptable to wear in the workplace.)
Would be great to see a more in-depth examination of each section.

James Marwood

I really like the concept Simon, and I tend to use something similar in my own casual dress. I have my workwear items, my British items and my Ivy stuff. There is a fair degree of overlap, but generally it works.

I was interested to see you mention Hilfigger. A lot of the chaps I work with really like it, but I’m generally in agreement with William Gibson on the brand, that is an essentially soulless reworking of RL, being itself a reworking of Americana mixed with Ivy, as a rehash on traditional British menswear.

“There must be some Tommy Hilfiger event horizon, beyond which it is impossible to be more derivative, more removed from the source, more devoid of soul.”


Excellent entry, Simon, as usual.

A few observations:

– I believe a large part of Drake’s success is their talent in mixing traditional British country patterns with more a relaxed / natural cut you’d normally associate with Italy. It’s not an accident that their jackets are made by Belvest and their trousers (I think) by Rota.

– British country style, which has my preference, is indeed difficult to wear in warmer weather, case in point in Hong Kong where I live. An interesting, and often overlooked alternative, is the Continental take on British country, as seen in Spain where it had to be adjusted to the local weather. I am very partial to Teba style jackets, which can be made in tweed / wool for cooler months, or linen / light mohair for summer.

– In the same vein, some workwear items can cross over and easily be dressed up, as long as the style / cut is appropriate. I am thinking about Vetra blazers in this category


Great article and a great perspective. Could I dare to suggest a sixth style? That would be a Miami style. I’m from Southern Florida and there tends to be a unique set of fashion rules for color, selection, and fit. For instance, we have dress sandals and shorts separate from casual sandals and shorts – a subtle nuance, but none the less, a difference. And, no one, but a tourist, would be caught dead in a flowered Hawaiian shirt.

andrew hughes

Hi Simon,

What is your take on white trousers or jeans?


andrew hughes

Thanks Simon. Much appreciated. I’ve been looking at a Orslow and Bonacoura


Good grief. I just want a perfect fitting pair of navy chinos that doesn’t bunch at the waist 32″, and the butt is huge and fits mine that has done loads of deadlifting.

Given it was “just khakis” I thought I could or it, and while the latter wasn’t a massive failure the cuff is just too narrow.

Where do I go if I what to top out below £350 after alterations? If price was no limit?


Any advice on how to style some moleskin and corduroy trousers to get the British Country look? Would the corduroy trousers carry over into the American Prep?

Would you do side adjusters (buttons) or belt loops? Turn-ups? Pleats? Will leg width matter if I want to wear with rain boots while hiking around the property?

I am in the process of commissioning corn and dk olive corduroy (355g) and dk brown moleskin (410g) from Brisbane Moss. I would like to be able to have the dark trousers work with tweed jackets in town as well, like fall dinner parties/BBQs, brewery visits, or fall festivals.

Mr. Alex

Gentlemen, do you think that now Korean fashion also affects the fifth paradigm? I? Yes! I think so. And this happened recently, right before our eyes.


Hello simon
I want your advice how i can combine a heavy checked over shirt with other clothes


Thank you very much for your advice


White bucks, not ducks.


Mr Crompton, I am about purchasing an OTR sports jacket and I found one that is nice to me, but it features patch pockets while also featuring welted breast pocket. When looking for an English style coat, is that ok or is it a big mistake to mix these different types of pocket on the same jacket? Thank you very much.

Daniel Jordan

Dear Simon,
I read [and indeed frequently re-read] this article. I was particularly struck by your comments on the “Italian smooth”. Would it be a paradigm that you might consider devoting a stand-alone “how to build a wardrobe” article on?

I am seeking guidance specifically on the nature of an “evolving” wardrobe. Less about the cross-over zones between the paradigms you have categorised here, but more about how one’s tastes shifts over time and how one’s wardrobe reflects different phases in life. In my case for most of my twenties I was firmly planted in classic preppy / Ivy-League category: boldly coloured chinos worn with tweed jackets/blazers. However, now I’m in my mid-30s this aesthetic no longer suits my lifestyle nor my personality. My taste has shifted much closer to the more discreet smooth Italian/continental style that you discuss in above, where the subtleties of tone and texture are more important than statement colours.

One problem with this “transition” is what to retain from my preppy/Ivy wardrobe and what needs replacing across jackets/shirts/trousers/shoes/accessories etc?

Secondly (and this is where I feel some genuine anxiety due to my unfamiliarity with the style), is how do I cultivate a contemporary Italian/continental style wardrobe, but managing to avoid an overly-stylised look (as if I just stepped out of a window display from a high street fashion store such as Reiss or Massimo Dutti)? In short, I am rather stuck trying to create a style that better reflects my age/taste/profession, without going too far in the other direction of looking excessively vogue/fashionable/modern.

Any and all advice would be most gratefully received!


I actually agree that it’d be great to see capsule wardrobes in each of the major paradigms (Italian smooth, British country, American prep), because I think a huge part of wardrobe building is how items fit together – not just the overall look.

I find my Luca Faloni knits in soft cool colours always gets worn with my Anglo-Italian jeans, but they don’t go so well with raw selvedge. Conversely, my heavier Scottish knits go well with the selvedge, but the warmer colours don’t quite go with the cooler washed jeans.

In fact, I’ve found I almost have two wardrobes – retro Italian Smooth and modern British Country – that don’t quite go together. As well planned as my wardrobe was planned in theory, I’d have double the options if I’d stuck to one paradigm.


Hello Simon. I am building my casual everyday wardrobe on Paradigm 4: Workwear. As you have suggested checked shirts, would you kindly specify in what cloths and colours as I intend to get a Khakhi colour 5 pockets trouser and two selvedge denims in Indigo and Mid-Blue colours as bottoms. Right now I want to focus on these three bottoms options. I intend to wear these pieces together with my Red Wings Iron Rangers 8085 in Copper Rough and Tough leather.

Thanks, Simon.


Thank you Simon for time and your valuable insights you have acquired and gained over the years. This is also my first experience writing on a menswear website. A good experience, I must say.

Daniel Y.

In terms of the “Italian Smooth” paradigm, you mentioned cashmere sweaters, but also mentioned roll necks and half-zip sweaters. Are you saying that this aesthetic is typically associated with cashmere roll necks and cashmere half-zip sweaters or are you referring to other sweater silhouettes for the cashmere sweater as well? Stepping back, I would assume that this aesthetic is heavily driven by various sorts of knitwear, do you think that the roll neck and the half-zip are pretty much the standard knitwear pieces that would be associated with the style or do you think there are some other styles that you would also include (crewneck, full-zip, etc.). If so, which ones?


Alright, so you’re saying that in general any and all cashmere knitwear can be included in this look, but the most identifiable examples would typically be a roll neck, a half-zip, and a full-zip. In terms of half-zip vs. full-zip, could you expand a bit more on that? Do you think that one is better than the other or that one would be a better option for certain situation? If so, in what situations would you recommend each? Is there one that’s more common? Is there one that’s more versatile across the board? Also, for the cashmere knitwear, what colors would you recommend as part of the paradigm?


So, in your opinion, the full-zip would be completely ruled out, but the half-zip is alright given it is considered a staple for the “Italian cool” aesthetic, correct? You also mentioned a roll neck, but I tend to associate roll necks mostly with the winter/colder months. Further, you mentioned that the crew neck would also work (both within the “Italian cool” aesthetic, but also over a wider range of other casual aesthetics). Do you think that the crew neck sweater in a cashmere (like the one you linked) would also be considered a staple within the aesthetic of Brunello Cucinelli et al?
Also, you mentioned that you don’t personally like or wear zipped knitwear, but would you still say that it still has some form of staying power? It seems to be a recurring item in a lot of the Italian brands’ look books and I don’t tend to see as much crew necks. To me, it seems like they’re all just full of half-zips and roll necks. Do you think that the half-zip could be considered a staple or is it just a fad?


Dear Simon,
I don’t really know where to write this, however I put it here because my “style” is, I think, the closest to British country. My query however is this.
I am a teacher; I am therefore required to dress smart but not too smart; as a result, I think a dark blue or grey two-piece suit is a little too corporate for work. I tend to favour a tweed jacket, plus tie and smart trousers and normally brogues however I have two gripes with this: one, it’s too hot (esp. in summer) and two, it can get a little repetitive.
I therefore write to you to ask what you recommend for an outfit for work which manages to be both smart but not corporate, flexible and lightweight? Or have I just a $64,000 question?! I thought something Neapolitan might be suitable but I will defer, obviously, to your better judgment.


No, I have not but I shall read it straightaway. Thank you! Hb


Great article and very thought provoking. A useful thought exercise. I think it is also interesting to think how one’s own regional customs play into the categories. For example, a flannel (particularly Buffalo Plaid) and a touque are ubiquitous workwear where I am.

Not sports

Ooh missed streetwear.

David Tillinghast

Simon, such an excellent overview, as all of your articles are. I am wondering where the classic menswear of the 1930’s and 40’s cinema (classic British) fits into this model. It seems to me to separate and fundamental stylistic paradigm that continues to influence to this day (Thomas Mastronardi in New York is a fairly pure example of this). I would love to hear your knowledgeable take on this!

Cormac Lynch

This is one of my favorite articles here. These paradigms are highly useful in understanding the influence of aesthetics of many popular brands. Also, as a reader, I get clarity into how to combine various aesthetics without losing harmony.
I majorly dress in moderately slim cut workwear, mostly military influenced, with some elements taken from British country in day, and Italian smooth in night. And, I must confess, my choices are evolving, as I find comfort in newer options that align with my style.
Great day ahead.

Cormac Lynch

Btw, I’d really appreciate to know that how you define secondary and primary clothing.
It would be good to understand the terminology for me. I presumed that primary clothing meant what you would typically wear but secondary for special occasions such as hunting (British country), or extreme weather conditions (such as Covert coats in Winter). Thank you.

Lasse Hansen

A lovely read as usual Simon! I definitely dress mainly (and have done so for a long time) with an Italian/Scandinavian aesthetic both in formal dress and more causally. Though, having gardening and house projects as a hobby and having two dogs, a cat and now four birds (building a bird aviary is the next home project) I really long for more work wear inspired looks to kinda go with my more at home lifestyle. My problem is that most inspirations that I find online for workwear doesn’t really seem to be summer suitable. I live in Ecuador so wearing several layers of rough heavy material isn’t really that comfortable. Any inspiration sources for more tropical weather friendly workwear style?

Best regards,


Would darker denim shirt and dark wash denim be classified as workwear because they are smarter than their medium and light counterparts?


The main problem with casual outfits is that it becomes difficult to include elegant pieces in the wardrobe sometimes due to social propreity. For ex as you have suggested a lot of times if everybody is wearing tshirt, jeans and sneakers most of the times there is one upgrade in the form of a casual shirt or casual loafers which though smarter would necessarilly be workwear. There is nothing elegant about my overall outfit. Can a person appear stylish even without an addition of an elegant piece in the outfit?