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Top hat
How to spot it: tall, flat-crowned and broad-brimmed, usually in black or gray silk or felt, and impossible to mistake for anything else.
When to wear it: almost never by default. It was everyday wear for gentlemen through the 19th century, but today it belongs with morning dress at weddings and the Royal Enclosure at Ascot, or with white tie. Buy one only for a dress code that names it.
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Homburg hat
How to spot it: a stiff felt crown with a single dent running front to back, no side pinches, and a brim that curls up all the way around with a ribbon-bound edge. The picture shows Winston Churchill wearing one in Downing Street in 1943.
When to wear it: the dressiest felt hat a man is likely to own, a step above the fedora and a step below the top hat. It sits best with a dark overcoat or a suit at a winter wedding, a memorial or a formal evening, and looks out of place with anything casual.
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Bowler hat
How to spot it: a hard, rounded dome of a crown with no dents at all and a short brim curled up at the sides. In America it is usually called a derby.
When to wear it: it was designed in London in 1849 as a tough riding hat that would not be knocked off by low branches, and it still has that sturdy, sit-straight look. Today it suits formal city dress, costume and anyone who wants a hat with real character; it reads as deliberate, so wear it with confidence.
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Fedora
How to spot it: a soft felt crown creased lengthwise down the middle and pinched at the front on both sides, with a brim usually around two to three inches wide that can be snapped down at the front.
When to wear it: the all-rounder of formal hats, at home with a suit, an overcoat or a smart jacket and jeans. A wider brim balances a broader face and shoulders. The name comes from Victorien Sardou's play Fédora, first staged in 1882.
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Trilby
How to spot it: a fedora's sharper cousin. The brim is short, often two inches or less, angled down at the front and turned up sharply at the back, and the crown is deeply indented with a pinch at the front.
When to wear it: it is meant to sit toward the back of the head and suits narrower faces and slimmer builds better than a wide fedora. It works with smart-casual clothes as well as tailoring. The name comes from George du Maurier's 1894 novel Trilby.
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Pork pie hat
How to spot it: a flat-topped crown with a circular or oval crease running around the top, like the dish of a pie, and a short brim usually turned up all around.
When to wear it: the jazz musician's hat, and the most playful of the felt styles. It is low enough to suit shorter faces and does not overwhelm a small frame. Felt versions suit cool evenings out; straw ones make a good summer alternative to the fedora at an outdoor music festival.
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Panama hat
How to spot it: a Panama is a material, not a shape. It is hand-woven in Ecuador from toquilla palm straw, most often shaped like a fedora, and the finest weaves feel almost like linen.
When to wear it: the classic hot-weather hat with a linen suit, at a garden party, a summer wedding or anywhere humid. The name stuck because the hats were sold in Panama, to travelers crossing the isthmus and later to the workers building the canal. In 2012 UNESCO added Ecuador's toquilla straw weaving to its intangible cultural heritage list.
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Boater
How to spot it: a stiff, braided straw hat with a perfectly flat top, a flat, level brim and a grosgrain ribbon band. Where a Panama is soft, a boater is rigid.
When to wear it: summer only, with a blazer. It is still part of the dress code at the Henley Royal Regatta and other rowing events, and barbershop quartets made it their signature. Off the water it is a bold choice for a summer wedding or a day at the races.
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Cowboy hat
How to spot it: a high crown, usually creased, and a wide brim curved up at the sides, in felt for cooler months or straw for summer.
When to wear it: built as working gear for ranch hands, and it still earns its keep against sun and rain outdoors. John B. Stetson's Boss of the Plains, with a 4-inch rounded crown, became the template after 1865. Away from the ranch it fits rodeos, country concerts and Western-themed events; with city tailoring it reads as a costume.
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Cloche hat
How to spot it: a fitted, bell-shaped crown pulled low over the forehead, with little or no brim. It made its name in the 1920s, worn with bobbed hair.
When to wear it: the easiest vintage-look hat to carry off, because it hugs the head and shows off the eyes and cheekbones. Felt versions suit fall and winter coats; straw ones suit a summer dress. It is a good pick for a 1920s-themed party.
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Pillbox hat
How to spot it: a small, brimless hat with straight sides and a flat top, like a round box, worn toward the back of the head or tilted to one side.
When to wear it: a neat, structured choice for weddings, christenings, church and other daytime occasions, especially matched to a coat or suit. Jacqueline Kennedy's pillbox, made by Halston for the 1961 inauguration, is the version most people picture.
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Fascinator
How to spot it: not really a hat. It is a decorative headpiece of feathers, flowers, net or sinamay fixed to a headband, comb or clip, with no crown to speak of.
When to wear it: weddings, the races and other daytime events where a full hat feels too much. Check the dress code first: in Royal Ascot's Royal Enclosure a hat with a solid base of four inches or more is required instead, while the Queen Anne Enclosure accepts a fascinator.
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Sun hat
How to spot it: any hat whose brim is wide enough to shade the face, neck and shoulders, often a floppy straw or cotton brim of four inches or more over a simple low crown.
When to wear it: the beach, the pool, gardening, a resort vacation or a long day outdoors at a summer festival. It is the practical answer when shade matters more than style, and a packable one that holds its shape after being rolled is worth the extra cost.
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Beret
How to spot it: a soft, round, flat-topped cap with no brim, usually knitted or felted wool, often with a leather sweatband inside.
When to wear it: the Basque version is worn pushed to one side or back for a relaxed, artistic look and keeps the head warm without flattening a hairstyle much. Military berets are shaped down hard over one ear. It folds into a pocket, which makes it a handy cold-weather hat for travel.
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Flat cap
How to spot it: a rounded cap cut in one smooth, flat piece that slopes forward to a small stiff brim, sitting close to the head with the peak higher at the back. It is also called an ivy cap.
When to wear it: the country and weekend hat, with tweed, a waxed jacket or a sweater. It is sleeker than a newsboy, so it suits a smarter casual outfit, and in wool it is one of the warmest brimmed caps for fall walks.
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Newsboy cap
How to spot it: the flat cap's fuller cousin. The body is usually built from eight panels meeting at a button on top, so it looks puffier and rounder, over a small brim.
When to wear it: casual and a little retro, with corduroy, a peacoat or denim. The extra volume flatters a rounder or fuller face more than a slim flat cap does, and it is a popular pick for vintage-styled events.
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Baseball cap
How to spot it: a soft, rounded crown of six panels with a button on top and a long stiff bill at the front, either curved or flat. Fitted caps have a sized band; snapbacks and strapbacks adjust at the back.
When to wear it: the default casual hat for sun, sport, errands and travel. A curved bill and low crown look quieter; a flat bill and tall structured front read as streetwear. Leave it off at a sit-down dinner or any event with a dress code.
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Bucket hat
How to spot it: a soft, crushable, unstructured hat with a short round crown and a wide brim that slopes downward all the way around, usually in cotton, canvas or denim.
When to wear it: festivals, the beach, fishing and any casual day when shade beats looks. It began in early 1900s Ireland as a wool felt hat for farmers and fishermen, and it still packs flat in a bag better than almost anything else on this list.
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Boonie hat
How to spot it: like a bucket hat but wider and floppier, often with a band of fabric loops around the crown, side vents and a chin cord, in quick-drying cotton or nylon.
When to wear it: hiking, fishing, safaris and hot-climate travel, where its military roots in tropical heat show. The chin cord keeps it on in wind and on boats. It is purely practical, so choose it for the trail rather than the town.
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Knit cap
How to spot it: a close-fitting knitted cap with no brim, often with a folded cuff and sometimes a pom-pom. Americans usually call it a beanie; elsewhere it may be a toque or a watch cap.
When to wear it: cold weather, full stop. A cuffed, fine-knit beanie in a plain color looks tidiest with a wool coat; a chunky or slouchy one suits weekends and the ski lodge. It is the one hat on this list nobody will ever think is trying too hard.
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