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A Gentleman’s Guide

The Way To Wear Your Hat

Whether you favour a beanie, a baseball cap or a broad-rimmed fedora, try these on for size

  • Guerreisms

The hat is arguably the most potent accessory in a well-dressed man’s arsenal – it can make a persuasive or a regrettable impression. So it’s important to get it right; though the hat covers a man’s head it reveals his character. It should be worn with confidence. Wear it reluctantly or ambivalently and there’s the danger that the hat will wear you. But don’t be timid. The dressing landscape has evolved and there’s nothing to fear about striking out in the world in a hat that suits you.

The challenge, really, is to make the hat yours. Like velvet jackets and leather bags, a good hat looks better with age. Wear it in, wear it often and wear it until people associate you with it. Remember: wear something once and it’s novel, the second time it’s familiar, the third time it’s your signature. Also consider your proportions. It won’t surprise you that big hats look better on big heads. As a devoted hat wearer I prefer large, straight brims – they frame the face in a flattering way, drawing focus to the eyes.  

Don’t be afraid of idiosyncrasy – a good hat looks personal. My ragged Panama is missing its band, which makes the crown appear taller, and suits my rather large head. (Fellow men with large heads: admit your situation then find a hat to suit!) I wore the same beaten up baseball hat every time I went fly fishing for 10 years. It was there through triumphs and ones that got away. When I lost it in Yellowstone National Park I was forlorn, and convinced that it was responsible for me going fish-less the next two days. Yes, hats are powerful.

So let’s consider some classic hats and what they say about their wearers.

The Fedora

  • Guerreisms

A natty hat, the fedora evokes classic style with a slight sense of raffishness. Traditionally, the brim turns gently down in the front and slightly up at the back. It’s survived some disagreeable associations with boy bands in T-shirts (we’re looking at you *NSYNC), and has remained a mark of distinction throughout the 20th century. Yes, the fedora endures – take it from no less an authority than pioneering journalist and author Mr Gay Talese. “I have been wearing fedoras since boyhood,” he says. “My father was a very stylish custom tailor, and he told me once: ‘No man is fully dressed without a hat’.” Mr Talese learnt this lesson well, and owns about 40 hats. He wears his fedoras with a suit and tie, and you would do well to follow his lead. The grey rabbit-felt Larose fedora paired with a Kingsman double-breasted chalk-striped suit, will distinguish you in any setting. The black Borsalino fedora has a touch of a Rat Pack vibe – and would look downright audacious with the MP di Massimo Piombo tuxedo jacket. Go forth with fortitude. As Mr Talese says, “Hats enhance one’s appearance. They add to (never detract from) one’s individual sense of style.”

try some of these

  • Larose Zip-Detailed Rabbit-Felt Fedora Hat

  • Borsalino Rabbit-Felt Fedora Hat

  • Kingsman Charcoal Double-Breasted Chalk-Striped Suit

  • MP Massimo Piombo Contrast-Trim Bouclé Tweed Tuxedo Jacket

The Panama

  • Guerreisms

This is a warm-weather classic, as timeless as a Negroni. It began life as a staple of tropical destinations but these days it is perfectly acceptable in cities during warmer seasons. The street style photographer Mr K.E. Guerre of cult blog Guerreisms, looks particularly striking in a Panama. He claims he hasn’t left his house without a hat since 2006. “A hat is a tool which when used correctly is a statement piece,” he says. What does a Panama say about its wearer? That he celebrates the season and welcomes a fresh accessory into his wardrobe. Lock & Co Hatters, the standard-bearer of English hat-making, offers a white Panama that pairs perfectly with a light grey Wooster + Lardini suit and a Drake’s knit tie. Paul Smith’s rugged take on a Panama has thicker weave. It’s less delicate and belongs on the beach with Vilebrequin swimming trunks.

try some of these

  • Lock & Co Hatters Classic Woven-Straw Panama Hat

  • Paul Smith Woven Straw Hat

  • Wooster + Lardini Grey Prince of Wales Check Wool Blazer

  • Vilebrequin Moorea Mid-Length Printed Swim Shorts

The Baseball Cap

  • Tommy Ton/ Trunk Archive

Most men have worn a baseball cap at some time in their lives. Their ubiquity has led some men to raise their cap game. Mr Eugene Tong, style director of Details magazine in New York, manages to make the look his own. “I have a shaved head and I wear a hat every day,” he says. “I used to wear Chicago Bulls hats since I was a big Michael Jordan fan. I’d wear them until they disintegrated.” These days he takes better care of his caps, but still likes the challenge of figuring out how to wear them everywhere. “I managed to wear a black Acne Studios hat to a black tie event,” he says. “That was a challenge and it worked.” A green AMI cap works well with everything, including a Levi’s Vintage Clothing sweatshirt. Unstructured blazers and baseball hats play well together: try an Ebbets Field Flannels cap and a cotton Alex Mill blazer.

try some of these

  • AMI Cotton-Blend Baseball Cap

  • Ebbets Field Flannels 1936 New York Black Yankees Wool-Broadcloth Baseball Cap

  • Levi's Vintage Clothing 1950s Cotton-Jersey Crew Neck Sweatshirt

  • Alex Mill Slim-Fit Ripstop Cotton Blazer

The beanie

  • Tommy Ton/ Trunk Archive

The beanie is a rugged, masculine hat, worn in the Navy, on the docks and by Mr Frank Serpico. However, in 2015, you’ll find beanies in more elegant fabrics than their woolly predecessors, such as the cashmere offered by LA’s The Elder Statesman, and they remain popular even among those who’ve never wrestled with anything more demanding than the keyboard of a MacBook. And for good reason – it’s a hat that is as comforting as it is practical. “I started to wear a beanie when I was around eight, and red has always been my favourite colour,” says Mr Alexandre Mattiussi, the designer behind Paris-based brand AMI. “It feels very protective.” Mr Aaron Levine, vice president of men’s design at Club Monaco gets right to the point: “They’re functional, they’re simple, they’re timeless – they’re a safety blanket for your head.” A wool Richard James beanie is a versatile option: wear it with a Berluti cardigan or an unconstructed Gant Rugger blazer. The Thom Browne striped Donegal beanie is more robust and would look great with outerwear that has a nautical tradition, such as the Tomas Maier peacoat.

try some of these

  • Richard James Two-Tone Wool Beanie

  • Thom Browne Striped Donegal Wool and Cashmere-Blend Beanie Hat

  • Gant Rugger Unstructured Cotton And Linen-Blend Blazer

  • Tomas Maier Wool-Blend Peacoat

the flat cap

  • Jacopo Raule/ Getty Images

The tweed flat cap once carried English hunting overtones, but it has migrated out of the country and looks good in nearly any setting. It has been worn by everybody from American newsboys (successfully) to the Norwegian curling team at the 2014 winter Olympics (less so). Men respond to the flat cap because it’s an elegant take on a sporting look, more elevated than a baseball cap but less formal than a fedora. London-based tailor Mr Shaka Maidoh of sartorial blog Art Comes First, a man of many hats, has been wearing flat caps since he was seven. “The first hat I ever remember owning as a kid was a flat cap my father got for me that I had to choose,” he recalls. It’s a hat that suits all ages, and has been embraced by men as diverse as Prince Charles and Mr Dennis Hopper. The flat cap comes in many fabrics: Lock & Co Hatters offers one in denim that is right at home with a John Smedley textured cotton cardigan. A Musto Shooting tweed cap contrasts well with a Lutwyche blazer and Chimala jeans.

try some of these

  • Lock & Co Hatters Denim Flat Cap

  • Musto Shooting Checked Wool-Blend Tweed Flat Cap

  • John Smedley Textured-Knit Cotton Shawl-Cotton Cardigan

  • Lutwyche Blue Check Wool and Cashmere-Blend Blazer

the trilby

  • Tullio M. Puglia/ Getty Images

The trilby (pictured here on ex-footballer Mr Hidetoshi Nakata) looks like a fedora, with a smaller brim that traditionally slopes sharply down in front and up at the back. It’s a hat that has been around since the late 19th century and so has a classic element to it. Sir Sean Connery’s James Bond wore one with his Savile Row suits, and he looked dashing with a hint of playfulness. A more contemporary example of someone who wears it well is London hatmaker Mr Anthony La Touche, who is known as Mr Hat. He inherited both his first hat – a black rabbit fur-felt trilby – and then his love of hats generally from his grandfather.  “He was never seen without a hat and now neither am I,” says Mr La Touche. A trilby leaves an impression, particularly with sharp, well-tailored jackets – this is the first port of call for those looking to add a hat to their formal or working wardrobe. A Larose grey trilby would look perfect with a white Richard James linen suit jacket.  Or brighten up your look with Paul Smith’s straw trilby paired with A.P.C.’s geometric print shirt.

try some of these

  • Larose Rabbit Felt Trilby Hat

  • Paul Smith Cotton-Trimmed Straw Trilby Hat

  • Richard James Off-White Slim-Fit Linen Suit Jacket

  • A.P.C. Slim-Fit Printed Cotton Shirt