Anonymous asked: I would really like to start wearing hats with some of my outfits. I own a few, but whenever I put them on, I feel like it’s too much & end up not wearing them. I’m partial to fedoras. I’ve never tried to pull off the skater/trucker hat, but I’ve always wanted to. Any ideas for fedoras, skater/trucker, or hats in general? & what kinds of dos/don’ts with outfits?
My friend A.D. says: haaaaaa, my eternal question.
Here’s the deal: if you wear it right, nothing is too much. But I understand your issue; hats are tricky, especially fedoras. Even though I’m not partial to fedoras (my head is a weird shape), I think fedoras can be worn just about anywhere. They look especially good when paired with dapper items, like collared shirts, oxfords, ties, etc. (Extra points if you wear a fedora on a date!) I’ve seen people rock them in jean shorts and T-shirts, too. The key to wearing a fedora (or any hat, really) is confidence. You’re wearing this cool/vintage-y hat, and it’s right there on top of your head with no place to hide.
Swag/confidence is required for skater/trucker hats, too, but it’s a different type of confidence. Fedora says, “Yeah, I know I’m wearing this, and I look damn good!” Skater/trucker says, “Bro, I’m cool and silly, and I know it.” Skater/truckers are rocked best when paired with some skinny jeans/tank top OR shorts/shirt (or tank).