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Style GirlfriendStyle Girlfriend is the go-to destination for guys seeking not just fashion advice, but lifestyle tips, tricks, and shortcuts - all from a friendly, female editorial team’s perspective. Each week, Team SG will round up the clothes, grooming products and more men need to live their most stylish lives.

I generally think National [Blank] Days are stupid, but I’ll make an exception for National Hat Day, now celebrated in the year of our lord 2020 on January 15. Bankrolled by Big Beanie, no doubt,!) presents a useful opportunity to highlight all the great headwear you could be wearing. Because, real talk, the whole hat universe has gotten the shaft with guys for too long.

And I get it. In the early aughts, you saw Justin Timberlake in his post-NSYNC/Justified era onstage wearing something brimmed with a feather on the side looking oh-so-smooth, thought to yourself, “I can pull that off!” Tried it. Realized, “No, I absolutely can’t!” and went back to your baseball hats.


But it’s the roaring ‘20s! We’re older and wiser now.

So below, check out four #SGapproved hat styles to get you out of your baseball cap rut:

Brixton Wesley Fedora, $47
Bailey Nelles Fedora, $115
Graphic: Ana Luisa Suarez

When you look back on your boy band-inspired efforts at trendy headwear, you probably think about the fedora (and curse the tagged Facebook pictures to this day!). In fact, what you more likely were wearing was a trilby hat.

Now, knowing the difference between a trilby and a fedora is sort of like knowing the difference between a blucher and an oxford dress shoe…it means you’re way more invested in menswear than most of us (including me).


But since we’re here: The fedora is worn forward on your head and has a wider brim that’s often flat and straight around. Trilby hats, on the other hand, have more narrow brims and are perched farther back on the head.

Personally, I really like a guy in a fedora, so long as it’s made from sturdy materials and fits well. The vibe is very “Hemsworth brother landing in LAX on a nonstop from Sydney.”

It’s also quite functional, with the large brim providing useful cover on sunny days. Wear yours with a trucker jacket and corduroy pants in the winter, and later in summer with a white pocket tee and casually cuffed chinos.


Think of a dad hat like a baseball cap that went to Parsons. Devoid of team allegiance, this headwear is all about FASHUN. I mean, it’s also about keeping you from squinting when outside, but mostly we’re talking trend.


Don’t be afraid to get a little bit cheeky, like with the ‘babe’ hat below. Or, opt for a style in a non-sports color, like the millennial pink hat. Also good? Repping a brand that you haven’t worn since middle school (think: Tommy Hilfiger, Nautica, and more).

Wear yours like you would any baseball cap, duh, and wait to modestly deflect the “Ooh I love your hat” compliments that are sure to roll in.

RVCA Bucket Hat, $40
Stetson Bucket Hat, $36
Graphic: Ana Luisa Suarez

When the godparent of all four of LL Cool J’s children, the bucket hat, came back into style, I’ll admit that our team was wary. At best. The aesthetic is so specific that it’s easy to look like you’re wearing a Halloween costume, or appropriating a culture that’s not yours (or both).


That said, the bucket hat is really comfortable! And easy to want to pull on with casual outfits! If you’re curious to bring it back into your wardrobe repertoire, I’d advise skipping the ‘90s, Kangol-esque styles. Go with a neutral color, or even a camo pattern, for a more “urban safari” effect.


Saved this for last since it’s most likely the easiest sell, and y’know, all this typing makes me tired. Despite it being 60 degrees in NYC this week, it’s still winter! And will be winter for several more months! If you haven’t upgraded your cold-weather beanie since high school, there’s no better time. You can find plenty of winter accessories already on sale, and you’ll still get some mileage out of it before the last snow melts.

Megan Collins started Style Girlfriend to help guys look and feel their best. Today, she and her team share tips, tricks, and shortcuts to a closet that inspires confidence.

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