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The Prep Club · Jun 26, 2026

In “less-than-stylish” cities

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Callum Giles · The Prep Club

We know the stylish cities, the big four of fashion: London, Milan, Paris, New York, but also Florence, Tokyo, Berlin, possibly Copenhagen. You can quite easily sus out if a city is fashionable by opening Instagram, searching city name + “street style”, and seeing how many results you can find. In the case of “less stylish” towns, the carousels and short form videos will quickly revert back to one of those listed above, especially if they happen to be in the same country (outside of the States).

I am fascinated by the towns which fly under the radar as a result, the places with no reputation, that don’t have internationally covered fashion weeks or trade shows or swathes of vintage clothing stores. The cities without cameras on each corner, or people hoping to be photographed. Because it’s not like everyone in these towns walks around in the buck, and any large enough metropolitan area is going to produce a sort of naturally emerging visual language informed by climate, culture, peoples.

The Prep Club is in session, check last week’s short meeting for thoughts on uniforms and curation here. Also, make use of The Directory, the alphabetised, as-comprehensive-as-possible guide to heritage, niche, and vintage preppy menswear:

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Naples is a frenetic, electric town, densely populated, chaotic, grungy. It’s perfect fodder for those who dare to ask “what if Anthony Bourdain had posted to his Instagram story instead of making television?” In this way it has a certain fashionable quality, as a trendy destination, especially as we’re creeping into a grunge revival, but it’s not somewhere you’d go to shop. There’s two kinds of immediately visible tourists in that city, the classic American in their cargo shorts and their slight bewilderment, and then there’s the guy in the linen suit, dressed like we’re in Milan or Florence. Neither has the sense that they belong because Naples has its own language when it comes to clothing, and it’s a mile away from anything you might have seen at Pitti Uomo last week, anything you know from The Talented Mr Ripley, and it’s all the more interesting for it.

Right now, Naples is all big sneakers: Asics, New Balance, or Nike Air Max, with long shorts and big t-shirts or with 501s and a shirt vaguely draped over top. It’s a mostly practical style which speaks to a town with greater concerns than fashion, clothes need to suit blazing around on mopeds. For those concerned especially with vanity it’s brand heavy, big emblazoned designer labels and the like. It’s loud, the most typically stylish gentleman I saw was wearing a bright orange Polo button-down over wide leg khakis and Birkenstock sandals. And that’s all hardly surprising, there’s a sense that this town has, over the years, had to shout to be heard.

The elephant in the room is that Naples is poorer than Milan or Florence, and forever in the shadow of a fierce and ominous mountain. The common thread in the cities we uphold as bastions for style and taste is their wealth; we like to think that it’s no longer the arbiter of style, and though it may not be in the way it was in the late nineteenth and early twentieth centuries, fashion remains a prohibitive, costly endeavour or is considered frivolous for those with lower incomes.

“Chicness” or “coolness” demands a certain amount of exclusivity, expense is the easiest way to achieve that, otherwise it comes through physical obfuscation, being appointment only, hidden or far away, many a store in Tokyo benefits from that sort of obscurity. Often it’s both, take ultra-exclusive London store Adret as a fine example of that. I think there’s a quiet desire for “stylish” cities to be somewhat prohibitive, and by that what I really mean is expensive.

With all due respect dear reader, I doubt that you batted an eyelid when I omitted Lagos and Kinshasa from my opening list of stylish cities. Africa as a continent rarely gets adequate air time in fashion conversations. I don’t think it’s outlandish to suggest that the established criteria for what makes a stylish town tends towards the West and the Global North. There are a number of biases at play there. First, an assumption that certain places aren’t affluent or “developed” when they are, and then after that an assumption that fashion, art, expression, are luxuries rather than the lifeblood of human vitality.

The city I call home these days does not hold a reputation as expressly stylish. Leeds has always been a working town, built around fabric milling, sure, but never reaping the spoils, the bolts of cloth being sent elsewhere to be made into suits and dresses. When clothing production arrived it was industrial, not tailored, a bastion of ready-to-wear.

This is notable because the typical response I might expect upon asking why the big four are undisputed as style capitals is that “that’s where the industry is”. But the industry was, and to some extent still is, here. Abraham Moon are still here, Burberry still hold an office. I’ve held down three jobs in fashion across four years. At times it feels like, in the industry, this is a town with hands but no voice.

The small foothold that Leeds does hold in contemporary menswear is owed mostly to one store, which is set to close its doors at the end of the month. I need you to understand that HIP store has been, over the years, fucking revolutionary. The first place to import Supreme to the UK, from punk through to British streetwear pioneers, right at the forefront for years until JD Sports acquired a stake back in twenty-fourteen. When this store opened there weren’t contemporaries or competitors. Yet, in the four years I’ve lived here I’ve never really gotten the sense that one of the most important multi-brand stores in the UK called it home, even with All Blues Co., MKI Miyuki Zoku, and Glorydays, Leeds seems to forever be exporting it’s fashion. HIP closing its doors is a rather sorry sight, a step backwards for a town which I think is long overdue it’s flowers (or the very least a working mass transit system). Then again it’s perhaps a little too accessible to ever be a truly “stylish” city, that’s half of why I like it.

There are a hundred and one guides to London, Tokyo, Milan, to their shops and bars and Michelin restaurants, whilst there are a hundred more cities with fascinating fashion languages besides. I long to investigate further, to find out what exactly clothing means to the people of “less-than-stylish” cities, one day when the budget allows you can expect that.

And here’s the thing, coming back from Naples I’ve been wearing my 992s with shorts, and I don’t think I would have done so with quite so much regularity otherwise, cause that’s a cool look, man, whether it’s contemporary be damned. We needn’t be looking up to these pedestal-standing places all the time, casting a wide net brings in a greater variety of influences, which can only be a good thing. I’ll admit I can be a snob at times, but when it comes to cities worth exploring for their fashion, it’s about time we looked further afield than the old guard.

Prep Club adjourned, catch you next week.

Excess, uniformity, curation

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Jun 19

It’s a short one this week, I’d hoped to be back at full steam but a combination of still nursing burnout and having to move house directly after coming back from vacation mean that a full fat issue of THE RADAR so as to keep to schedule isn’t feasible this week, I hope you fine club members can appreciate that.

Read the original on theprepclub.substack.com

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