For every stylish guy pulling off a fedora well there’s a gang of them that look awkward, uncomfortable or downright bad. Given how flawlessly characters like Roger Sterling and Don Draper wear them through every season of Mad Men, you’d think it would be easy, but not necessarily so.
I’m not a hat wearer myself (the double XL size of my head doesn’t exactly help), so I brought in my friend Justin Power from Pioneer Goods to provide the looks for this shoot. All the hats featured were lent to us by the friendly folks over at Goorin Bros in Harvard Square.
To help out my you guys trying to figure it out, here’s a short list of do’s – and don’ts – to point you in the direction.
- Skip the feather: Hats aren’t the usual so they’ll draw a lot of attention. Keep the look as simple and sleek as possible by skipping the feather altogether. Don’t worry, you’ll still get noticed.
- Keep the brim small: The wider the brim, the trickier it will be to make it work. Go for a thin brim on a hat like a pork pie rather than a wide, floppy one.
- Let it be the focal point of your outfit: If you’re opting to wear one, keep the rest of your outfits simple. Opt for muted earthy colors rather than that floral shirt you’ve been waiting to break out all winter.
- Don’t skimp on quality: American made, wool hats look beautiful. Their thin cotton counterparts look terrible. You do the math.
- Dress them down: If you’re going to wear a suit, skip the hat. You’re not going to look like Don Draper, you’re going to look like you bought a pimp costume for Halloween. T-shirts, denim button downs and chunky sweaters will do just fine here.
- Push the brim up: The front of a fedora has can flip up, making for a more casual vibe. It’ll show the world that you’re not taking it too seriously (which you aren’t, right?).
There’s no doubt that this is a tough one to pull off. It’s not for everyone and certainly not for the weak-of-heart. One final thing to note though, if you do go for it...just own it.
Thank you to Justin for stepping in front of the camera for this shoot. Thanks to Goorin Bros. Harvard Square for lending us the gear. Shot on location at the Harvard Arboretum in Jamaica Plain, MA.