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I’m 35 and a guy I’ve been hanging out with since college wears a baseball hat every time he steps out of his house. He even wears it to work even though he works inside an office. It’s a really casual place so he’s not getting in any trouble, but I tell him women just don’t take guys seriously who wear hats all the time. He says he likes his hats and women tell him he looks “cute” in them. Who’s right?
As with all things, whether or not baseball hats look good depends on where you wear them, who you’re with, what the occasion is, and so forth. If you live a casual life–your work environment permits casual wear, and your hobbies require casual wear, and the company you keep dresses casually–then a baseball hat is appropriate. And also monotonous, safe, and liable to induce narcolepsy.
The biggest issue I see with baseball hats is that they limit what you wear on the rest of your body. You’re not going to wear a baseball hat with a sharp blazer or a button-down shirt; you won’t wear a baseball hat with fine shoes or pressed pants. If you’re wearing a baseball hat every single day, you are probably living in jeans, sweats, and tennis shoes, which is…BORING. Maybe your friend doesn’t care about style…in fact I’d wager a good amount of money that he doesn’t care about style, which is fine. We don’t judge here. Well, I do, of course, but that’s why I’m paid the big bucks.
As to whether women will take him “seriously”…I think women’s feelings on baseball hats vary in ways that their feelings on, say, clean underwear and cockroaches in the bathroom, don’t. A woman who herself dresses very casually and prefers an evening at Buffalo Wild Wings to a night of stiletto heels and martini-tasting will likely find a man in a baseball hat to be a good match for her. Now if your friend is wearing his hat to wine bars during happy hour and then wondering why none of the professionally-dressed women are interested in him, he needs to either adjust his expectations or take that thing off his head.
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Editor’s Note: Baseball hats also recently came up in our “growing up your style” feature. To read that, click on over here. And what’s your take? Do you wear baseball hats? When? And for the record, this is one baseball hat I think any guy who’s ever seen “The Natural” would love to wear: