Wear it Well: Men's Hats
Hone in on the right hat for you
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
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.
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.
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.
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