How to Rock a Hat

Mar 28, 2012

Looking to update your look but not sure where to start? From the top, of course. Baseball players have their caps. Boarders (snow and skate) have their beanies. But for everyday style, how do you rock a hat like JT, Brad Pitt or Johnny Depp without looking like a poser?

First, check your wannabe style. Make your topper fit your personality. Then consult this list and see what suits you best.


For the lover or the fighter, the bert is traditionally worn by artists and army men. In cool weather, a wool beret in place of a ski cap looks slick with a leather or wool jacket in a similar color. In warm weather, cultivate an artistic look with a black tee-shirt and jeans, and accessorize with an acoustic guitar under a tree to really kick up the look. Of course, you'll need to know how to play guitar first or you'll be entering serious poser country.


The cowboy hat brings irony and personality to a dressed-up look, especially if you live in cowboy country. But be careful with this look: unless you're goin' out on the range, don't pair it with jeans and a plaid shirt. 


Currently the choice of American Idol contestants and musicians in general. Also Johnny Depp, Justin Bieber and other celebs about town. Made of wool, tweed, felt or fur felt, this signature topper is creased in the crown and pinched in the front and usually has a ribbon and the occasional feather for extra "jazz". Formerly the look of 1920s gangsters and 1940s musicals, but updated with a smaller brim and also called a "Trilby". Looks great when paired with a preppy fall layered outfit, especially a tweed jacket.

Greek fisherman

If you're into the yachting scene or are interested in going out on a fashion limb, check this style out. In summer they come in white cotton. Cooler weather styles come in dark leather or wool. One of the many hats of choice seen on Ryan, Sharpay's twin brother, in the High School Musical movies. This pairs well with a nautical look - reds, whites and navy blues, layered clothes and thick vertical stripes.

Ivy cap

Also called a Kangol or a Flat Cap, this brimless hat with a rounded top has its roots in 1920's newsboys, the Great Gatsby, and old Ivy League golfers. Sources tell that Kangol is an acronym: K from "knitted", ANG from "angora", and OL from "wool". Currently pairs well with hip-hop style: brands like Phat Farm, Sean John and Rocawear.

Hat Etiquette

Always mind your manners. Hats off in class and when singing the National Anthem. Bonus: a guy who removes his hat when dining in a restaurant gets extra points in any polite girl's book.

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What is Your Favorite Type of Hat?

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  • Beanie.
  • Sombrero.
  • Visor.

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