The other day I had lunch with a female friend when she said something that was somehow banal and bizarre at the same time.

“I’m very open-minded,” she began. “I once slept with a guy who wore a HAT, for christssake.”

I had no idea that wearing a hat was a type of eccentricity to a woman. My ideas of hats typically either go in the direction of Mad Men era fedoras or damn-it’s-frickin’-cold-outside beanies. I don’t wake up in the morning and think about adding a hat as a finishing touch to my outfit. But why not? Men have fewer options when it comes to getting dressed, so we should use every weapon in our arsenal.

Of course, hats are an easy piece to mess up. The fedora has been co-opted by Red Pill Meninists, so that’s an automatic NO. Rather, I’d prefer a hat that doesn’t evoke feelings of disgust for the ladies. Something like…

(Click on the titles to see our Polyvore collection of hat and leather shoe combos.)

The Pendleton Indy Hat with The Newman Chukka Boot in Marrone

You hear “indie” and immediate think of that girl you dated who listened to WAY too much Belle & Sebastian, but luckily I still associate the word with the original: Indiana Jones. That’s the exact look you’ll pull off when you top with The Pendleton Indy Hat. With its wide brim and Scotchgard® wool material it’s not only fashionable, it’s functional too. The best pair of leather shoes to match with the Indy Hat must have the same combination of style and substance. We can’t think of a better pairing than The Newman Chukka Boot in Marrone. These two accessories will make your outfit sporty, casual, and ready for any adventure—even if that adventure is as trivial as running down the street to get bagels.

The A. Kurtz 'Riley Ivy' Driving Cap with The McQueen Driving Shoe in Cognac

Pairing a driving cap with a driving shoe is a no-brainer. They are both comfortable, casual, and evoke a vintage aesthetic that makes your entire look cohesive. The A. Kurtz ‘Riley Ivy’ Driving Cap is the perfect shape; it’s just curved enough with a short brim that will look stylish, not cheesy. The McQueen Driving Shoe in Cognac has the same stylistic feel, with the added bonus of being one of the most comfortable and easy-going shoes in our collection. Our advice is to keep the rest of your outfit simple. Think cuffed chinos and a plaid button down. Also, don’t forget the matching belt to go with the shoes.

The New Era 39Thirty NY Yankees Speckle Fitted Cap with The Legend High-Top Sneaker in Blue