Effortlessly Casual: How to Wear a Baseball Hat with Regular Clothes

Let’s talk about how to wear a baseball hat with regular clothes. The pandemic has, no surprise, had a lot of us resorting to athleisure on a regular basis, but I’m of the mind that you can break the baseball hat out of the activewear box. Of course, I love a fall hat, but sometimes you’re going for a more effortless look.

How to Wear a Baseball Hat with Regular Clothes

That’s why I love a baseball hat with regular clothes. It has this cool, casual, just-threw-it-on look that’s perfect for weekends, traveling, brunch, the list goes on.

If I’m going to wear a baseball hat with activewear, I’m not thinking too much about what’s on the hat. It might be a white hat with a logo, it could have a print, it doesn’t matter. That’s all about function.

But, if I’m wearing a baseball hat with regular clothes, I do put a bit more thought into it. I want a hat that’s a solid, preferably garment dyed or waxed cotton for a lived in look. I’ll pair it with jeans and a simple button down or sweater. I’ll throw on loafers or boots. I’ll accessorize with simple jewelry like gold hoops or pearl studs.

The key here? Keeping it casual but not dressed down too much. A t-shirt or sneakers would be too literal. You want to pair it with elevated basics that feel effortless rather than careless.

how to wear a baseball hat - baseball hat with regular clothes


Other Outfit Details

Curious about the other items in this outfit? The baseball hat is a UVA hat from the UVA bookstore — it’s this Skinny V Hat in Navy (I also love the Stone color!). I picked up the waxed vest when I was at the L.L. Bean outlet in Portland. It’s my absolute favorite now, I swear I’ve worn it almost every day.

The jeans are H&M and I wrote a full review here. The sweater is old J.Crew but this turtleneck or this cashmere mock neck are similar options this season. The booties are also old but this pair looks similar in color and height (height is always what trips me up when it comes to buying booties, you need short enough to wear with jeans but high enough to make sense!). Lastly, the wooden watch is the Cassia from Jord Watches.


how to wear a baseball hat - baseball hat with regular clothes


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