Guide to Wearing Men’s Hats With Suits

Only a true master of his sartorial domain is ready to pull off the elusive suit and hat combo. Indeed, while peripheral arenas like shoes and watches offer a variety of acceptable options, it’s usually a mere hat or two that can fashionably top off a given outfit. The key, of course, is knowing which men’s hat goes with which men’s suit or get-up, something easier said than done. Are we being a little hyperbolic? Perhaps. On the other hand, we’d rather you proceed with caution than rock the wrong hat and suit combo and look the fool. That’s why we’ve compiled a Guide to Wearing Men’s Hats with Suits just for all the smooth criminals out there. Read on and style accordingly.

two men wear hat and walk

This article is part of our Suited and Booted Series


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stylish panama hat

Panama

Typically light in both weight and colour, a stylish Panama hat is your best warm weather friend and a beacon of fun-loving vibes. Originally hailing from Ecuador, Panama hats are most often made using the plaited leaves of a toquilla palm plant (which is technically not a palm but close enough to it). As a result, the hat is sturdy in construction and highly breathable. Being a summer and spring time accessory, the Panama hat blends nicely with seasonal wear like a crisp linen suit.

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pork pie hat

Pork pie Hat

Worn by the likes of Buster Keaton and Walter White (aka Heisenberg), the Pork pie hat derived its name by loosely resembling British pork pie. As a close cousin to the fedora, these small and round men’s hats host flat crowns, creases along the inside top edge, and brims that curl slightly upward. When it comes to pork pie hat and suit combos, the hat usually finds its place within the smart casual dress code. Picture a navy blue blazer, a button down shirt, khaki pants, a pocket square and a felt pork pie hat and you’re heading in the right direction.

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trilby hat

Trilby

Sporting a low angle brim and pure retro vibe, the trilby occupies its own tiny corner in the men’s hat arena. You might recognise it as the hat Inspector Clouseau wore in the Pink Panther films, as well as multiple appearances atop the crown of Mr. Bruno Mars. And although you might think trying to pull of the trilby is venturing into dangerous territory, the trilby has become one of the more socially acceptable pieces of headwear. When you find a trilby with the right shape, fit and proportions, it looks pretty damn fine with a suit.

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derby hat

Derby

Like the trilby, the derby (or bowler) hat is definitely an acquired taste. Commonly made of hard felt, the hat features a short brim and rounded crown. Historically, these men’s hats have been associated with blue collar and bourgeois alike. Nowadays, the derby is often viewed as a somewhat humorous accessory emanating with antiquated charm. Should you wear one, pair it with a classic three-piece suit and maybe a cane and you’ll certainly draw some eyeballs. Just be sure to tip it kindly when any high society Victorian women pass by.

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fedora hat

Fedora

Once a mainstay of the business world, the fedora hat has broadened in appeal over the course of its long tenure. To spot these occasionally popular men’s hats, look for the indented crown with a lengthwise crease pinched near the front on both sides, along with a soft brim of about 2.5 inches or more. Should you buy one, make sure it’s high in quality, and keep the brim up. Back in the day, fedora hats and suits used to come in one package, creating a uniform vibe. Nowadays, you can probably get away with buying the fedora separately, but you’ll still want to make sure it compliments your suit to perfection. And if you’re pairing the hat with a smart casual outfit, a kung fu grip on personal style is pretty much mandatory. If your reflection in the mirror is reminiscent of an early 2000s Justin Timberlake, then it’s best to remove the hat.

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flat cap

Flat Cap

Similar to a newsboy hat, the flat cap hosts a rounded top and a small, hard brim up front. These men’s hats are typically made of tweed, though other fabric variations (like leather or denim) do exist. In spite of the flat cap’s history among working class types, it’s recently emerged as dressy weekend wear for younger men. Pair it with a tweed jacket, handsome sweater or maybe a nice blazer with khakis, and go have a nice picnic in the countryside. Or you can just do brunch–whatever works for you.

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newsboy hat

Newsboy Hat

Wildly popular at the turn of the 20th century, the newsboy hat is embraced by both male and female tastemakers. The hat is defined by a curved brim, eight panels and a top button. Thanks to the use of materials like wool, the hat makes for functional and fashionable cold-weather wear. There’s no need to go too fancy with this one–pair it with a smart casual or straight casual outfit and you’re ready to rock. If it’s good enough for David Beckham, it’s certainly good enough for you. Just don’t overdo it on size.

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men wearing hat with suit

mens blue flat cap

men wear white hat

all different collection stylish hats

men wear black derby hat

men wear off white cap

men wear blue cap

men sitting white collar cap

men wear panama black cap

two men wear derby cap

men brown cap wear

men wear newsboy cap

peoples wear various types cap

men wear black tribly cap

This article is part of our Suited and Booted Series

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A Guide to Men’s Dress Codes
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