How to Wear a Hat That Flatters You

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5 Ways to Wear a Hat With Style

Getty Images / Melodie Jeng, Timur Emek

Hats are intimidating for many people, we know that. Aside from hiding a bad hair day or shielding yourself from the sun when necessary, many of us avoid adding hats into our everyday or style-driven wardrobes. Perhaps we're afraid they're "too much" or perhaps we're worried they won't flatter our faces properly.

Here's the good news: That's 99 percent not true. The biggest battle with hats is finding one that fits your head properly, which comes down to actual sizes in some cases, but also proportions.

The main thing with hats is finding one that suits your style. In the winter months hats like beanies become a necessity (and we'll talk about those, too), but don't discount more fashion-forward looks like wide-brim hats, berets, and more.

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How to Style a Wide-Brim Hat

Getty Images / Melodie Jeng, Kirstin Sinclair, Christian, Vierig

Wide-brim hats might be our favorite hat silhouette of the moment, but its roots are timeless. From cowboys to Old Hollywood screen sirens, these hats have taken many forms and flattered many different looks. That still holds true today, with so many different brim widths and crown shapes, you can find one that matches virtually any sense of style, season, and outfit.

For fall and winter, felt hats are great for holding in warmth and throwing off weather. Black is a go-to color, of course, but don't discount olive green, cognac, grey, and even white. The truth of the matter is that you'll have to try on a few different hats to find the silhouettes and size that work for you. An extra-wide brim might not work for everyone, but here's one thing we do know — until the winds of fashion change, fedoras with small brims are to be avoided at all costs.

Shop the look: We love the selection of high-quality hats from Goorin Bros. and Nordstrom.

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How to Style a Beret

Getty Images / Melodie Jeng, Vanni Bassetti

Oh la la, the beret! This French-style hat can become costume-y very easily, so proceed with caution. Take a cue from the ladies above and make sure your beret is paired with a chic suit, a great coat or your most casual jeans. No striped tops, nothing red, nothing else about your outfit should scream "French," if you catch our drift.

Shop the look: There's a rainbow of berets available from

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How to Style a Beanie

Getty Images / Kirstin Sinclair, Timur Emek, Melodie Jeng

When it really gets frigid, beanies are often a necessary part of winter style. They don't have to be itchy, droopy or goofy though — there are plenty of stylish and simple beanies that will complement your professional wardrobe as well as your weekend attire. We love the cashmere beanies from places like Everlane and Uniqlo, as well as the playful knits with colors and pom-poms and embroidered details like beading and sparkle.

Shop the look: Find a few of our favorites from Nordstrom, Ugg, and Madewell.

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How to Style a Greek Fisherman's Cap

Getty Images / Kirstin Sinclair, Starfly

If you're ready for a hat that's anything but typical — and actually very traditional — try a Greek fisherman's cap. These hats are a cross between a newsboy and a beret, and have a structured band that will sit firmly on your head. We love this style as an addition to your weekend uniform — wear it with jeans, sweaters, and a menswear-inspired coat. This hat will attract eyes, make no mistake, so pairing it with fussier looks isn't a good move. Think of the Greek fisherman's cap like a baseball cap with an extra dose of style.

Shop the look: There's a variety of Greek fisherman's caps available from

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How to Style a Baseball Cap

Getty Images / Melodie Jeng

Ah, the classic baseball cap. Take cues from the J. Crew catalog for how to wear a baseball hat in a preppy, stylish way — otherwise, wear it with whatever you want! Pick a team, a logo, a city — and rep it. Baseball caps are great for hiding a mediocre hair day, or throw it on to make any outfit a bit more casual.

Shop the look: We have a few favorites from J. Crew and of course, nothing beats a classic NY Yankee's cap. (If you're a fan, that is.)