Work an Old-School Hat Into Your Modern Wardrobe

  • , by Alex Torres
  • 3 min reading time

How creative do you get with your style? If you're adept with accessories and know your way around a cloche (or any other type of fashionable hat), you can easily figure out how to defy convention and work an old-school topper into your everyday wardrobe. Those who love fashion but don't necessarily know how to make a vintage-inspired hat fit in with modern-day attire can take a cue from these helpful tips.

What Is Vintage?

First, you should understand what qualifies as a vintage hat. A women's baseball hat or a men's warehouse hat don't count as vintage. In fact, those are examples of casual wear. Old-school options include dainty styles with brims and other fashionable hats, such as cloches, fedoras, Bretons, and pillboxes. Some styles, like turbans and toques, may be more appropriate for costume parties than day-to-day life, but there's no reason you can't experiment to determine the styles that will work best for you and your look.

The Fabulous Fedora


Men's fedora hats rank up there with crisp overcoats and tailored trousers as some of the most essential pieces in a perfectly polished wardrobe. It's reminiscent of style's old guard: Frank Sinatra, Gene Kelly, and Humphrey Bogart all wore fedoras like they were born with one on. That's the key to a modern day man's ability to rock the famed fedora-you have to own it. Is it raining outside? Throw on your trench coa- not that trusty windbreaker you wear to campus or grab on your way to the office, but an actual trench coat-and watch your look go from basic to bold. A scarf at your neck ties it all up nicely, and gives you a polished finishing touch. If you're working the party circuit, a men's fedora hat looks fabulous with a pair of tailored pants, a silk vest, and a white shirt. Bottom line: If you're going to wear the hat, you've got to the dress the part.

The Curious Cloche


Among fashionable hats for women, few are as eye-catching as the sophisticated cloche hat. A decidedly posh alternative to a women's winter hat with ear flaps, the cloche is designed to keep your head warm and add some class to your cold-weather style game. This cute women's winter hat wears well in the spring and fall, too, particularly if the breeze picks up. Throw it on before you head outside in your drop-waist dress, which mimics the styles favored by women in the 1920s. It was during that period when cloches truly made their name, both for their style potential and their ability to add some warmth without destroying an intricate hairstyle. The beauty of the cloche is that it wears well with your favorite modern ensembles- try it with a pair of wool pants, pumps, and an elegant blouse in the fall for a look that channels something straight from the early 20th century. And of course, a little red lipstick wouldn't hurt, either.

The Pork Pie

Vintage hat

The pork pie hat has history on its side. It's a favorite among men whose look falls somewhere between hot and hipster- a kind of meeting of the sartorial minds. George Michael sported his throughout the late 1980s, and Justin Timberlake still wears his all over the place-post 'N Sync, no less. It's not specifically a musician's favorite, and you don't have to be a singer to wear it today. This fashionable men's hat is surprisingly easy to pull off in the everyday world. Try it with a T-shirt and jeans on extra casual days. When it's cold, use it for its functionality and layer up with a scarf, sweater, and coat. There's no real science to this one, which is great for anyone who wants to pull off a vintage-inspired style without a tremendous amount of effort.

Now that you have all of these tips at your disposal, which hat will you try next?

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