Style Girlfriend Reader Question: It seems like baseball caps get a bad rap when it comes to men’s style. When is a baseball cap acceptable headwear?

I think the baseball cap is underrated. It’s really a surprisingly style-conscious and complementary part of a man’s wardrobe.

Why? For starters, a baseball cap is one of the best ways for a guy to instantly show something of his personality. Women have tons of options for expressing themselves – skirts, dresses, weird culottes that look like a skirt but are really shorts… Pile jewelry and accessories on top of that, and a girl has about a trillion and two ways for her outfit to say, “This is who I am.” Guys have – thankfully, or unfortunately, depending on how much you enjoy digging into your closet each morning – fewer options to convey personality through their clothes. So accessories play a bigger role.

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A well-chosen baseball hat says a lot about a guy. Because – and allow me to speak in grand sweeping generalizations here for a moment – guys are into sports. Their chosen or inherited team(s) can be as much a part of their upbringing as Sunday dinners at their great aunt Melinda’s. Maybe more so. So when a guy sports a baseball cap touting his beloved (insert team name here), it’s expressing a piece of himself the same way a woman would wear her grandmother’s wedding ring on a chain around her neck, or her mother’s fur coat when she’s old enough to appreciate it. Guys’ love of sports is (again, generally) passed down from their fathers. I can remember my brother and dad bonding over their disdain for Glenn Robinson’s lack of defense at the dinner table when I was younger. So in that way, the baseball cap as accessory can serve as a nod to family ties as well.

Beyond all that, baseball caps on guys look cute! As long as we’re not talking straight-brim, right out the Lids store shopping bag, hologram stickers still on, style of cap. Because that look is terrible. It doesn’t even deserve to be called a “look.”

I also find it totally bizarre when a guy reps a team’s cap just because he likes the colors. You should not be thinking about it that much. But a guy sporting a well-worn hat bearing his hometown pride? Yes please.

So what makes a great baseball cap? For starters, duration of ownership. Longer is better. Think about it, your favorite hat is the one you’ve had since forever. Second, character. A great baseball cap’s brim is perfectly bent. Free of visible sweat rings, but bearing scuffs and fading from years of use – those marks show that your hat has seen you through college exams and girlfriends and extra innings and rainy nights when you forgot a jacket.

Of course, there’s a time and a place for baseball caps. They are: at a bar, at a sporting event, in the park. Not the time and place: meeting your girlfriend’s parents the first time, on an interview, to church. So wear wisely.

Dapper Comment: We agree that caps should be reserved for outdoors or sports events. We encourage you to ‘step up your style’ for other functions.

Content provided courtesy of Style Girlfriend

Image by Adam Medders Photography