Hats have gone in and out of style over and over throughout history, from cowboy hats to fedoras; we have always loved something sitting on top of our heads. Of course, like most aspects of men’s clothing, there are dozens of options for any man to choose from, no matter what his style is. Some work best when topping off a wonderfully stylish ensemble, and others are simply used for blocking the sun. In any case, there is always a reason to put on a hat for any occasion, but which one is right for you in your situation?
Here we’ve put together a guide to some of today’s more common silhouettes. You’ll find anything from sun hats to sombreros, captain’s hats to flight caps, and berets to balaclavas — there are so many variations and evolutions of styles, we couldn’t fit them all.
A hat should complement your face, not hide it. Round shapes like bowlers and beanies will emphasize a rounder face, while the longer, taller lines of a fedora may complement those features better. Wider brims will exaggerate wide faces and can make narrow faces look even thinner. Watch out for extreme styles that you may buy for fun but only wear once or twice. Spend some time in a hat shop with an expert salesperson and a mirror. But most of all, relax and have some fun with your new friend.
Also, choosing the right hat for the right situation is paramount to looking your best. Felt hats and beanies look good in the winter and the cooler months, while straw hats and baseball caps look best in the summer months. Choosing the hat that best fits your face shape, outfit, and environment are all paramount to looking great. Here are over a dozen different hat styles to choose from.
Although the base materials — straw and felt — couldn’t be more different, the way most common hat styles are shaped is basically the same. Straws are woven materials of everything from, well, actual wheat straw, to palm leaves to paper to polypropylene. Felt forms are made from fur — often rabbit, but beaver is considered the highest quality — or wool. Manufactured as more or less conical discs, the forms are then steamed into shape and stretched over blocks to be molded into their final silhouettes.
The simplest hat of all is probably the classic fez or tarboosh, a basic flat-topped cylinder, usually with a tassel attached. With its roots in the Ottoman Empire, it’s most often worn by men from Morocco (the hat takes its name from the Moroccan city). Here in the U.S., you might be able to pull off wearing one for fun, but in an age where cultural appropriation is frowned upon, it may be best to leave this style to the Shriners.
Now, take that basic cylindrical shape and add a brim, and you’ve got a boater. Since the fashion world is abuzz with the talk of a new “Roaring ‘20s” this Jazz Era favorite may be about to have a moment. The simple, elegant silhouette has always been a favorite for the Kentucky Derby crowd, but we also like it for summer weddings, or anytime with a pair of white jeans and a navy T-shirt.
Exaggerate the proportions of the boater a bit further, and you’ll have the favorite of Amish men. Favored in black felt for winter or straw for summer, it actually has a bit of a hipster vibe, and we’re all for the straw version’s wide brim for SPF protection.
Flatten the top, raise the cylinder, and decrease the brim size for the ultimate expression of formality, the classic top hat. Generally speaking, you’ll only wear it when invited to a white-tie gala, where you’ll also be required to wear a true tuxedo complete with tails. But seek out a rakish version a la Robert Downey, Jr.’s Dolittle, and you’ll be onto the perfect headgear for leading your merry troupe on an adventure, even if that escapade is an unruly night out on the town.
Bowler or derby
The bowler, or derby as it was more commonly known here in the U.S., is another variation on the theme: Just curl up the brim and round the top. Featured prominently in The Age of Innocence as well as A Clockwork Orange, while we think the silhouette is elegant, it’s still considered to be a bit much for anything short of a costume party. Wear it at your own risk.
The classic everyman hat from the 1950s, the fedora — or its close cousin, the trilby — is the style we associate with Frank Sinatra, Indiana Jones, and Johnny Depp. Note that you may also come across “snap brim” descriptions, which means that the brim may be worn down or “snapped up” as a choice. Either way, you’ve got to be confident to pull off wearing a fedora, but if you can wear it well, the style bestows an instant aura of distinction.
The straw Panama hat is the elegant summer version of the fedora. Despite the name, the authentic style originated in Ecuador, gaining the moniker when Teddy Roosevelt made the hat famous by wearing it while touring the under-construction Panama Canal. It is the perfect way to top off any beach look.
Pork pie or stingy brim
The fedora’s jazzier cousin, the pork pie is named for its round crown, with a flat top, but a single crease of varying severities running around the circumference of the top. These hats have had quite a ride since the ‘aughts, including a “starring role” on Bryan Cranston’s head in Breaking Bad, and might be considered a bit passé at this point. On the other hand, they’re easy to wear.
The cowboy hat is yet another style that can take some major cojones to pull off, but if you can, there is not another headwear choice short of a hard hat that says, “all man.” From classic styles that are rodeo-ready to rolled, distressed ones more suited for a country rock stage, the basic silhouette is really a fedora on steroids. While most forgo the peak in the front, the wider brim is designed for more effective protection from the elements.
Many of the other hats we wear are assembled in much the same way as a shirt or a pair of jeans. Fabrics are cut from patterns and then sewn together, and stiffening pieces like canvases, interfacing, or even cardboard or plastic in the case of a baseball hat’s bill.
The knit (or crocheted) beanie probably gives the baseball cap some serious competition for the most worn hat style. Its ubiquitous form allows for a myriad of design possibilities and, although originally more of a cool weather topper, can transcend seasons and climates. The simplicity of the style may make you think that the guy waiting for the valet to bring his lamb around is wearing the same hat as … well, the valet, but while one is cashmere, purchased from an upscale boutique, the other is a cheap viscose blend bought on the street. (Note that the Beanie may also be made from a soft cut-and-sewn material like polar fleece, flannel, or even down-filled poly.) Pom-poms on top are optional.
While all things 1990s are having their turn in fashion’s retro wheel, the bucket hat is one that we’re welcoming gladly. It’s a simple shape and construction means it’s easy to roll and stuff into a back pocket or glove box to keep it handy for protection from the sun or light rain. Spanning classes and seasons, the style crops up in pricey designer collections and mass market stores, while fur versions keep our noggins warm in winter and cotton canvas or even performance fabrics.
From the turn of the 19th-century street urchins to early 1970s pop icons, the newsboy cap offers the comfort of a baseball cap but with a lot more style. Netflix’s Peaky Blinders series has given the hat a boost in popularity, but its roomy crown also comes in handy for stashing away out-of-control, longer locks. While the more traditional version is made from wool, more extravagant versions can also be had in cashmere or leather. Corduroy is also a favorite, but cotton twill or linen and cotton blends are lightweight alternatives that may find their way to the golf course.
With a similar European background, the flat or driving cap has quite a history for such a simple silhouette. In 1571, the British Parliament decreed that, on Sundays and holidays, all “non-noble” males over six years of age wear woolen caps. Long after the act was repealed, the cap kept its status as the unofficial uniform of the working class. Here in the U.S., it’s become a weekend go-to with a sporty 1970s vibe. Again, popularity for the style is further driven by period pieces like, again, Peaky Blinders or even Downton Abbey and by celebrities like Idris Alba rocking the look.
Is there an American male who doesn’t own at least one baseball cap? Even if you’re not a fan of the national pastime, this ubiquitous silhouette has wormed its way into just about every other sport — even if only as part of the off-the-field uniform — from golf to tennis to football (well, it’s not likely that football helmets will ever be part of our everyday wardrobe). A sweetheart of the corporate premiums industry and a gold mine for licensing of all sorts, the cap has unisex appeal and, depending on fabrics or finish, can be dressed up or down. The bill itself may be flat or curved, depending on your personal style. While there are so, so many options available, we do endorse going for the ultimate expression of the style, in an actual sized version, your home team logo optional.
See above but make it (small “d”) democratic. There is something appealing about one size fits all, especially when it’s adjustable, so it actually might fit the whole team (or department, school, etc.). Another 1990s throwback, the snapback, was elevated to a style icon when it was adopted by hip-hop entertainers. The dad hat version is more likely to be made from washed-down cotton or cotton-like fabric, and the curved brim is pretty much a must. This normcore favorite should also have the nerdy Velcro adjustable strap in the back or a simple slide. Finally, the trucker is like the silicone implanted doppelgänger of the baseball cap, featuring a foam-supported crown section that will retain its shape through just about anything a monster truck rally can throw at it, with a mesh rear section to keep things cool and dry.
While the classic trapper may conjure some comic moments — Elmer Fudd’s “Be very, very quiet,” or ” … I guess that was your accomplice in the woodchipper” from the movie Fargo — for those who venture into the cold, there is really no substitute. European fur trappers, who hunted the frozen territories of North America for beaver, originally wore the hats, using their handy ear flaps to ward off freezing temperatures and chilling winds. On warmer days, voila, the flaps can be tied up over the head and out of the way. Sherpa editions were later adopted by WWI pilots for missions that took them high into the subzero atmosphere. These days softer, more luxurious fur linings, not to mention faux, vegan-friendly alternatives, make the hat a favorite of urban hipsters, outdoor enthusiasts, and supermodels alike.
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