hat style guide

The Beginner’s Guide to Hats

Recommendations for your first-time purchase, plus insight on the season’s trendiest styles.

Hats are tough. They are one of those things that most of us love to look at but struggle to incorporate into our own daily ensembles because we’ve convinced ourselves they make us look silly. Then there’s also the hump of getting used to what you look like in one once you do begin wearing them. Regardless of how they make you feel, a hat is actually practical—no small feat in the fashion industry—whether the reason is to shield your face from the sun or to keep your head warm on a chilly winter’s day.

We thought we could use a little (or a lot of) help on the subject, so we consulted two experts in the field: Janessa Leoné of her eponymous and esteemed hat line, and Courtney Bagtazo, founder and designer of uber-cool brand Bagtazo. Lucky for us, they are dishing on everything from the season’s hottest trends (for the coldest weather) to their expert recommendations for your first-time hat purchase. In no time, they’ll have you ready to branch out from that single beanie that is currently the only hat in your cold-weather rotation.

Your First-Time Hat Purchase

“I always tell first-time hat customers (especially those that say, ‘I’m not a hat person!’) that the number one thing you need to pull off a hat is confidence. My recommendations for easing into hat wearing is to stick with a shorter brim and softer materials for starters—less structure in shape makes the hat easier to wear, which in turn makes you more relaxed and comfortable. I’d also suggest going for easy, neutral colors like black or a burnt brown—if it’s a color that can go with most things in your wardrobe, you’ll be more likely to wear it regularly, which will up your comfort and confidence level for hat wearing overall.” —Janessa Leoné
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“A first-time hat wearer should go as safe as possible. You want the hat to look like it was already part of your wardrobe, so unless you wear bright colors all the time, maybe wait on that fun-colored hat. Going for a shorter brim and smaller crown is usually a safe bet because hats can really draw attention, so a more low-profile hat will be best to ease yourself into the look. But I will add that a wide-brim hat tends to look good on everyone, it’s just a matter of whether the wearer is comfortable with it.” —Courtney Bagtazo
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According to the Trends

“With the pandemic still playing a major role in our day-to-day and keeping us at home (except for necessary outings, of course), trends this winter have prioritized functionality and ease of wear—from cozy but presentable sweat suits to wool hats that keep you warm while dining outdoors. There has been a natural gravitation towards soft, malleable styles like beanies or packable wool hats that are easy to fold into your purse when you walk into a store. And we’ve seen weather-resistant styles trending as well—waterproof suede bucket hats and headscarves are especially practical right now because more people are choosing to walk over taking public transportation—despite the weather outside.” —Janessa Leoné
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“The biggest trends for winter this year so far have been structured berets and pillboxes. I’ve been seeing smaller hats that sit close to the head to keep you warm all over the city.” —Courtney Bagtazo
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Expert-Recommended Styles to Experiment With

“I always veer towards practicality when I get dressed, so the styles I’m excited about right now are for many of the same reasons I mentioned above. I’ve been holed up in Paris riding out the pandemic since late summer, and it’s been cold here for a while now. I’ve been living in Hazel—a wool hood/scarf combo. It’s so easy to throw on and truly keeps my head warm when I venture outside, while the scarf adds a protective layer over my face mask.” —Janessa Leoné
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“Personally, I am excited for styles with big crowns. In winter, having space above the head in your hat helps to keep you warm, and in summer the same space cools you off. I have been in the mood to pull some looks with my masks, so the bigger or higher the crown, the better!” —Courtney Bagtazo
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