I like to wear hats. I always have. What started in high school as an effective way to not deal with styling my hair, became a habit that turned into a "personal style." I think there comes a point, probably in your early twenties where you have to decide, "Do I keep on wearing hats like a 'college kid,' or do i grow up and start acting like the man i am." I went with 'college kid.' (In my defense, I did then go back to college.)

But in actuality i think that ability to wear a hat is directly proportional to the ability to wear a hat without irony. And not everyone can do it. If you wear an ironic beret, i think you're a douche-bag (just my personal opinion). You have to feel in your gut that you look good in that cap, fedora, poker-brimmed hat, obscene message trucker hat, red sox helmet, etc. That's the trick. Lucky for me, I look great in them all.