It’s not long since baring your barnet meant flicking two fingers to the man. But the hat’s social status has declined from its post-war ubiquity, buried first by a counterculture that went mainstream, then a photogenic president, who became the first to appear bareheaded at his inauguration.

Since JFK put a bullet in the fedora, covering up has carried mixed connotations. Don Draper’s headwear is now more often seen on the kind of guys who think ‘negging’ is an appropriate way to snare a mate, and even more wearable options come with the caveat that you need to accessorise with Yeezy levels of confidence.

But now, millinery is having a moment. Blame period dramas like Peaky Blinders and Mad Men; blame the intertwining of skate and hip-hop cultures; blame global warming and its tendency to turn your weather forecast into a lottery prediction. But adding a little extra up top is no longer just a way to disguise a growing forehead.

It’s time to doff your cap to the new breed.

You Can Keep Your Hat On

Winter hats are functional beasts. But look at the bucket hat’s revival as a warning lesson against discounting form. As with everything you wear, picking right means knowing it’s appropriate. Therefore, it’s time to give up on the idea your boss will ever OK that snapback. Even if it is cashmere.

Some rules of thumb: styles that cover your ears are less formal than those that don’t; thick and woven materials are more casual than anything stiff and felted; if your granddad would wear it, it probably goes with your suit; and if your jackets are more Supreme than Savile Row, don’t think you can swing a fedora like a streetwear Frank Sinatra.

One quick note on etiquette: the hat comes off in private rooms. Which means you’re cool to stay covered on your way into the restaurant, but stow your fez once you hit the dining room. Ideally for good.

The Beanie

Men's Winter Knitted Beanies

Sometimes it’s the simple things men get most wrong. The humble beanie, a cone of wool designed to protect workers outdoors, has become Brian Harvey’s experiments with gravity, David Beckham’s drooping prophylactic, and the uniform of every lumberjack-cum-creative director infesting East London. Today, you’re shooting for pared-back colours in equally minimalist silhouettes.

Look for shades that work with the season’s key tones – camel, burgundy, grey and military greens – so it gels with what you’re wearing. If you’re in head-to-toe neutrals then going cherry on top isn’t the finishing touch you’d think.

ASOS Fisherman Beanie Hat In Green Twist - click to buyOLIVER SPENCER NAVY BASKET WEAVE WOOL BEANIE HAT - click to buyA.P.C. WOOL HAT - click to buyNORSE PROJECTS CLASSIC BEANIE - click to buy

The Baseball Cap

Men's Winter Baseball Caps

Courtesy of fancy fabrics and luxury co-signs, the baseball cap has graduated from subcultures to your everyday looks. If, that is, you pick up one in leather, felt or wool – materials that not only beat the weather but look sleek doing it. Just remember to wear yours the right way round.

Leave New Eras to Fred Durst and opt instead for less bulbous, five- and seven-panelled versions. The winds have changed on peak shape, too; turns out your dad was right and they do look better bent. Slightly. You don’t want people thinking you make a living playing poker online.

Must-cop skate brand Palace is the pick for streetwear kudos. If you’re more about cashmere than kickflips, stick to the high-end sportswear of Ami and Whistles.

WOOL STADIUM HAT - click to buyGANT RUGGER WOOL CAP - click to buyAMI Cashmere Baseball Cap - click to buywhistles baseball cap - click to buy

Dress Hats

Men's Winter Dress Hats - Fedoras, Trilbies, Pork Pie

A fedora doesn’t fight frost quite like an ushanka, but the besuited man needn’t arrive at work in January needing to thaw his head. Those summer versions of a trilby, fedora, pork pie or homburg won’t cut it when you can see your breath, so you need something thicker, in fur felt rather than wool. Which also avoids a drooping brim should you forget that umbrella we told you to get.

The winds that litter your driveway with broken tree limbs will be equally unkind to your new purchase if you pick the wrong size. So instead of buying online, head to a traditional milliner where you can sample in person, like Lock & Co Hatters and Christys’. Both of whose extensive histories mean they’ve probably got your ancestors’ head sizes on their books.

Classic Fedora Hat - click to buyOscar fedora - click to buyASOS Trilby Hat In Camel Felt - click to buyReiss Davies Wool Fedora Hat - click to buy

Flat Cap

Men's Winter Flat Caps

The working man’s hat has recently been stolen from shepherds by middle-class folk bands. Which has turned a cap honed on the weather-battered Yorkshire Dales into something that makes people suspect you’re carrying a banjo. But avoid beards, waistcoats and barn dances and the flat cap needn’t be entirely off limits.

Key is moving your look from country to city by opting for fabrics and designs lesser-spotted in country pubs. Tweed and corduroy are off-limits. Denim and technical fabrics less so.

You’re never going to wear a flat cap with an MA-1 jacket, but look to urban duds like jeans and a Harrington over waxed jackets. And don’t ever consider wearing it backwards unless you’ve starred in at least six Quentin Tarantino films.

M&S COLLECTION Pure Wool Flat Cap with Stormwear - click to buyG Star Raw Coban Flat Cap - click to buyLARDINI LINEN DENIM FLAT CAP - click to buyJohn Lewis Wool Moulded Flat Cap - click to buy