The Guide to Our Favorite Hats

  • Copy by: Valerie Chen

Sometimes, your ‘do resembles more of a don’t, and that first glance in the mirror gives a whole new meaning to “I woke up like this.” And sometimes, your stylish head-to-toe ensemble is missing a special accessory to top it off—literally.

Whether it’s a bad hair day, a sun-drenched beach day, a frosty snow day, or simply your run-of-the-mill Sunday morning, there are plenty of reasons to brush up on your chic hat game. Before you sit the bench and protest that you can’t pull off the lidded look, let the following guide to our favorite functional and fashionable hat styles persuade you otherwise. Honestly (bear with us here, it’s a punny road ahead), we really think you’ll find them rather cap-tivating. Dare we say, maybe even fe-dorable?


The Back Story: Long before the groan-inducing reference above, the fedora enjoyed its heyday in the 1930s to ‘50s. The word “fedora,” however, actually originates from the 1882 play “Fédora,” in which the heroine wore a soft felt, center-creased hat.

Claim to Fame: The gun-cocking, snake-fearing Indiana Jones rocked a classic fedora. Michael Jackson often crooned and danced while wearing a black felt version. Today, street style in NYC often showcases a fedora jauntily perched on a fashion maven’s head. 

How to Style It: The fedora is a style chameleon—bordering on masculine, it pairs well with feminine flair (e.g., red lips, floral prints, loose waves, and/or rich, jewel tones). At the same time, the fedora blends in with no-fuss, minimal ensembles, too.

Play with the variety of details select fedoras can afford, such as wide- or short-brim bands and sweet bows. During the day or summertime, a straw fedora (also known as a panama hat) is the perfect casual accoutrement. When night falls or temperatures drop, pick a darker, stiffer, or twill alternative for a more formal feel.

Shop Fedoras:

1. Sole Society | 2. Brixton | 3. Topshop


The Back Story: Sure, the floppy hat may technically fall under the category of fedora, but we’d argue the floppy hat or extra wide-brim fedora is a star in its own right. This less-structured type of fedora found its way to the hearts—or rather, the pretty little heads—of hippies in the 1960s and ‘70s.

Claim to Fame: Brigitte Bardot and Jane Birkin were two retro bombshells often photographed wearing the fashion essential. Today, we see style icons such as Kate Moss, Rachel Zoe, and Nicole Richie giving the circular hat a confident spin.

How to Style It: Considering the floppy hat radiates demure, bohemian vibes, try pairing it with similarly relaxed silhouettes and styles. Unpinned tresses, floaty dresses, wide-leg pants, silky shorts, and flimsy blouses? Yes, please! However, we do like the straw version paired with a little more structure (e.g., tailored pants or shorts and crisp oxford blouses) as a sharp complement to its more informal material and a sloping, almost undulating composition.

Wear the floppy hat to an outdoor brunch with friends, to the local farmers’ market, to a summer music festival, to a romantic trip overseas in Thailand or Greece, etc. — anywhere you may need extra protection from the sun.

Shop Floppy Hats:

1. Nastygal | 2. Old Navy | 3. H&M


The Back Story: Once upon a time, the first-ever baseball team, the Knickerbockers, wore full-brimmed straw hats. A “pillbox” cap associated with Chicago then became popular, before amateur baseball team Brooklyn Excelsiors presented their version in 1860. This one finally caught on and progressed into a cherished national icon: the baseball cap.

Claim to Fame: Babe Ruth, Jackie Robinson, and Lou Gehrig are among many iconic players who donned the easygoing chapeau. Nowadays, when off the field, it’s a street style favorite to achieve an undemanding, on-the-go demeanor. 

How to Style It: The baseball cap has transformed past its diamond boundaries of simplicity. It’s boomed in popularity in recent years, and now the cap is a home run for everyone — floral fans, color block fans, and stud/spike fans alike.

We delight in the off-duty nature of a baseball cap: A faux all-black leather cap goes well with a camo print jacket and a stripe dress. A worn-down vintage cap makes sense with denim cut-offs, a white tee, and trusty Converse sneaks.

Shop Baseball Caps:

1. Forever21 | 2. Madewell | 3. J.Crew


The Back Story: Also known as a skullcap or knit cap, the beanie was once solely associated with American blue-collar laborers who used the brimless cap to keep hair out of work’s way. The beanie has since found a home on many noggins in Canada, the United Kingdom, and beyond.

Claim to Fame: A recognizable beanie is red and roots for Team Zissou in Wes Anderson’s Life Aquatic, fashion model Cara Delevingne is another frequent beanie-wearer. Like the baseball cap, the beanie is habitually captured in street style snaps.

How to Style It: The beanie clocks in as part-time playful and part-time edgy, yet full-time laid-back. To emphasize the former, go with bright colors, patterns, and maybe a cute oversize pom at its top. Carry out the look with an analogously quirky leopard print coat.

To go edgy, we like slouchier, monochrome beanies paired with stylish items in a similar color palette (e.g. grey beanie with a black leather jacket and distressed white jeans). Braids are a no-fuss coiffure for beanies, but we can vouch for bangs that adorably peek out under the brim, as well as a clean, all-hair-tucked-under-and-away

Shop Beanies:

1. ASOS | 2. Club Monaco | 3. Need Supply


The Back Story: Versions similar to the iconic French beret have evidently been worn across Northern Europe, starting in the Bronze Age. A simple wool version labeled as the “Basque style beret” was a common accessory among peasants in Southern France. Later, militaries across the globe began to integrate the beret into their uniforms.

Claim to Fame: Certainly a well-known symbol, the beret is often associated with elegance and style (such as style icons Audrey Hepburn and Twiggy), in addition to power and rebellion (such as Argentine revolutionary Che Guevara). And we can’t forget about Picasso!

How to Style It: The beret is like the beanie’s sophisticated cousin who sips un café au lait at her favorite spot in Paris. So, do as French sophisticates do! Keep things effortless, and embrace black and white stripes, evenly distributed fits (oversize coat with skinny jeans, or a form-fitting tee with a voluminous midi skirt), muted hues, and a mostly fresh face under that sophisticated beret of yours. Have your locks frame your face (repeat after us: “hairpins are my friends”) under a slouchier fit. Très chic, n’est-ce pas?

Shop Berets:

1. Topshop | 2. Shoebuy | 3. Nordstrom


The Back Story: The trapper hat is part of the ushanka family, which consists of traditional, winter hats equipped with ear flaps that can be utilized for extra protection. Ushanka hats have deep roots in Russia, Scandinavia, Germany, and other regions prone to frigid weather. The trapper hat, in specific, also resembles the classic aviator cap, which became popular in the early 20th century as open-cockpit pilots needed protection and warmth.

No Fur, No Problem: The ushanka hat is traditionally made of real fur, but that kind of gives us the heebie-jeebies (though it’s really up to your own preference). Yet, there are many versions of the trapper hat that don’t involve the real stuff: the faux alternative, along with shearling, fleece, cable knit, plaid, and Fair Isle.

How to Style It: The trapper hat is the warmest of them all, says the Magic Mirror. Wear with just-as-cozy attire; avoid nonsensical shorts and summer dresses with this one. Also, because the trapper hat can be a “louder” item, pair it with softer and more subdued clothing items.

Shop Trapper Hats:

1. ASOS | 2. Macy’s | 3. Tory Burch

Do you often have a chapeau on? Or do you face each day hat-free? Any hat styling tips? Feel free to share!

IMAGE CREDITS: fedora image via Troup Rogue // baseball hat image via The Spicy Stiletto // beanie image via The Daybook // beret image via Ann Street Studio // trapper hat image via Miss Pouty