How To Wear A Flat Cap (Without Looking Like A Fool)

Style

Given its simplicity and practicality, it’s small wonder that the flat cap has almost global appeal. But then, while Peaky Blinders may have energised interest in it and its six or eight-panelled cousin the ‘baker boy’ style, the flat cap has been around since the 14th century.

Indeed, an Act of Parliament in the UK in 1571 made it mandatory to wear a woollen cloth cap on Sundays and public holidays – more as a boost to sheep farming than weekend style. But today, it’s all about aesthetics and what it can add to your look.

There are plenty of pitfalls of course, but these can be easily avoided if you know what you’re doing. The whole ‘faux-gentleman’ thing that embraced the flat cap (as well as the beard and exaggerated moustache) has come and gone, but it is possible to wear one and look both contemporary and cool.

What Is The Flat Cap?

There is, in fact, a genius inherent to this affordable and durable design: less formal than more structured hats – and so less off-putting for men who can’t, as it were, get their heads around hats – its design is still a deceptively clever one.

Cut deeper at the back, it has more purchase than it looks like it does – useful especially when lifting eyes to the sky while shooting, for example; the brim is short but still enough to shade eyes; and the whole thing is foldable, easily stowed inside a pocket.

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These are all notions nicked by spin-offs the likes of the driving cap, cycling cap and even the baseball cap. Perhaps the most appealing thing about the flat cap right now though is that it’s not a baseball cap. Ever understated, you’d never get a flat cap wearing some brash logo.

How To Wear A Flat Cap

Like its American equivalent, the baseball cap, the flat cap has an everyman quality to it, always as fitting atop a pigeon-fancying Yorkshireman as an estate-touring toff, whether working the land or owning it. It found a place in skinhead culture, but also hip hop and has been favoured by everyone from Del Boy to Samuel L. Jackson.

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Likewise, while it’s not a hat for all seasons – linen versions may work for summer, but the flat cap is essentially a cold-weather style – it is a hat for all occasions. Unlike the baseball cap, the flat cap is as at home with tailoring as with jeans and T-shirt, flattering most faces into the bargain.

Opting for one in a neutral colour such as navy or dark grey will offer up the most versatility. Introduce one as part of a monochrome look consisting of black tailored trousers, a grey T-shirt and a navy bomber jacket, and it’ll serve you well in a casual office environment as well as the weekend.

Wear It With

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Best Flat Cap Brands

Lock & Co

Unarguably one of the UK’s most esteemed men’s hatters – its namesake’s story in hat-making can be traced back to the 1750s, and the company is said to have invented the bowler hat – this is the place to go should you ever need a hot weather flat cap. They have styles in cashmere and Escorial wool, but also in linen.

Lock & co Hatters Bass flat cap - click to buy Lock & co Hatters Gresham flat cap - click to buy

Garrison Tailors

Yes, there really is an official ‘Peaky Blinders’ flat cap, not least because the TV show’s creator, Steven Knight, set up a company to make them and other clothing befitting a Brummie hoodlum at the turn of the last century. The English-made tweed style names? Arthur, Thomas and Shelby, of course.

Garrison Tailors SHELBY TWEED NEWS BOY CAP - click to buy Garrison Tailors THOMAS TWEED BAKER BOY CAP - click to buy

Bailey Hats

One of the all-time great American hat-makers, it was Bailey – once better known as Bailey of Hollywood – that made hats for all the big stars of the golden era of cinema, Gary Cooper and Cary Grant among them. Grant’s best hat moment? In None But the Lonely Heart, wearing a flat cap throughout. Bailey’s also makes them in showerproof cotton.

Bailey Hats Keter Flat Cap - click to buy Bailey Hats Galvin Newsboy Cap - click to buy

Kangol

Better known for its bucket hats – LL Cool J might spring to mind – Kangol is the definite headwear of hip-hop, despite being a British brand. In fact, it adopted its marsupial logo only in 1983 to deal with American’s persistently and puzzlingly asking for ‘Kangaroo’. Its cloche-like 504 flat cap is a classic.

Kangol 504 Wool Flat Cap - click to buy Kangol Tropic 504 Ventair Flat Cap - click to buy

Gamble & Gunn

Based on Portsea Island near Portsmouth, where a naval cap might be more in order, hat-makers Gamble & Gunn have built a deserved reputation for the bolder choice of materials from which it makes its caps, ochre Donegal tweed, suede and lux merino wool among them.

Gamble & Gunn Goodwood Cord Flat Cap - click to buy Gamble & Gunn Dolton flat cap - click to buy

Christys’

Established in Scotland in 1748 by one Miller Christy – his company would later win one of the first contracts to supply hats to the newly formed Metropolitan Police, while Queen Victoria’s consort Albert favoured their top hats – Christys’ offers flat caps in trad tweed but also hardwearing melton and moleskin.

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Borsalino

It was a Borsalino that Warren Beatty wore in Bonnie and Clyde, Humphrey Bogart in Casablanca and Harrison Ford as Indiana Jones – a tall crowned felt fedora that in time would take the name of its maker. But who’s to say the Italian hatter can’t turn its hand to caps? Its version, in fact, has an innovative multi-panelled back section for a closer fit.

Borsalino Pastoso Waterproof Flat Cap - click to buy Borsalino Gatsby Wool Flat Cap - click to buy
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