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Wear it Well: Men's Hats

Hone in on the right hat for you

By Brittany Hammonds | Jun 29 2015

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We’re just going to come out and say it – apart from baseball caps, hats are notoriously hard for guys to get right. Aiming for Cary Grant and looking more like K.Fed? Not ideal.

Don’t forego a millinery obsession just yet, though. Much like the shoes you wear or the scent you spritz, a great hat can take your style up a notch, setting you apart from your bare-headed brethren. Think of the iconic celebs who it’s hard to even picture not wearing one: Bogart, Sinatra, Depp. All very, very stylish dudes without a whiff of d-bag-ness (yup, that’s a word) about them.

Here at SG HQ, we want to help you realize your headwear fantasies. Paired with the right outfit, you could achieve style icon status in your own right – and that’s what were all here for anyway.

Below, a few popular men’s hat styles, and how to wear them:


Made its debut: 1881

How it got its name: Named after a French play, this hat was originally intended just for women. However, with its moderate brim and soft, customizable style, it quickly became a timeless men’s classic, too.

Who wears it: Humphrey Bogart, Indiana Jones

Jeans: Uniqlo, $50Shirt: Express, $35Hat: Brixton, $52 

Watch: MVMT, $110Shoes: Clarks, $130Bracelet: Kiel James Patrick, $40

Cologne: Jo Malone, $155

How to wear it well:

  • Fedoras look great on guys with a bigger build because of its taller crown and 2-inch brim.
  • Choose a moderate or wide brimmed fedora based on your build and face shape (wider brim for longer, oval faces).
  • Remember to choose to style based on seasonality – straw belongs in summer only.
  • Instead of plopping it straight on your head, tilt the hat back a bit for an effortlessly cool look.

Panama Hat

Made its debut: Early 1900’s

How it got its name: Deceptively not from Panama, but made famous from Roosevelt’s trip to the Panama Canal. Originating in Ecuador, the Panama Hat are lightweight, composed of weaved straw, and traditionally light-colored.

Who wears it: Of course worn by Roosevelt, this hat has also been made famous by Sean Connery, and Paul Newman.

Pants: Bonobos, $98Jacket: Suit Supply, $499 Hat: J.Crew, $65

Shirt: Banana Republic, $43Shoes: Jack Erwin, $95

How to wear it well:

  • When checking for quality, make sure the straw is tightly weaved (the old rule: it had to be able to hold water without leaking a drop)
  • The classic white Panama hat with a black band is traditionally formal, so it’s best paired with a summer-weight suit
  • Capitalize on the laid-back nature of the Panama hat by pairing it with loafers and linen
  • If you have a thinner face, make sure you wear a more narrow hat (conversely, a wider hat is better suited for a bigger face)
  • Lose the tie and loosen the top botton, for the ultimate laid-back vibe, then slip on a pair of driving loafers sans socks to complete the look

Pork Pie Hat

Made its debut: 1920’s

How it got its name: Aptly named for its pork pie resemblance, this recently revived style is usually made of felt or straw. The pork pie hat is quite short with a round crown, flat top, and flipped up brim all the way around.

Who wears it: Originally popularized by Buster Keaton; however, you may remember this bad boy being worn by Walter White in Breaking Bad. Now, you’re probably seeing it more than ever as it’s in a trending upswing.

Shorts: Gant, $78 | Shirt: Globe, $66 Hat: Bailey Waits, $70

Belt: Urban Outfitters, $29Shoes: Trigger Rands, $70Sunglasses: Asos, $19

How to wear it Well:

  • Since the pork pie hat is so round and short, it looks better on round faces as it tends to aesthetically cut off oval faces too much
  • Despite Mr.White’s straight on hat style… we suggest tilting the hat or wearing it a bit further back on your head to avoid looking costume-like
  • Pair the pork pie hat with slim-cut pieces because of it’s compact build (a small hat with loose clothing 
  • A straw pork pie hat looks great with a slim short sleeve button up, while a felt hat pairs well with a fitted blazer and tailored chinos

Tell me:

What would be your iconic hat style?

Want even more stylish headwear? Check out this article on baseball caps, and more summer favorites, like 7″ shorts and the versatile wedding suit.

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