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There’s a trendy hat for every moment: sun hats for summer, fedoras for fall, and beanies for winter. Some styles, like my best baseball caps, work all year round. Others, like bucket hats, are surging in popularity after a hiatus from the fashion scene.
"Fashion is forever changing, and certain decades and periods of fashion tend to always come back," celebrity stylist Zadrian Smith says. In the last two years, the style expert explains, bucket hats have been a "dominant force." "Every top designer has their own version of the bucket hat." Case in point: Bottega Veneta, Prada, Iro, and Ganni are just a sample of the labels backing the retro style.
Whether you’re investing in the bucket hat revival or you prefer a more timeless style, the rest of your outfit is the best guide for choosing a specific hat. "If you decide to wear an athleisure look, a baseball cap could be a great hat to wear, but also a fedora with sweats makes it cool and trendy,” Smith says. “Furthermore, matching your hat with your look to tie in a monochromatic feel brings out a fun, chic, and classic sense of style."
Ahead, shop the 25 best trendy hats to wear in every season.
A scallop-brimmed straw hat is going to block the sun while enhancing your summery look. It's practical and chic.
Perfect for vacation, this hat maintains its shape after being tucked away in your suitcase. It also has an interior adjustable band to customize its fit to your head.
A baseball cap is simply classic with jeans and a white T-shirt. If you aren't a Red Sox fan, 47 has a hat for every team.
Summer hats feel even more playful in a patchwork print like Arizona Love's. As temperatures rise, this style can add personality in an instant to easygoing outfits and matching sets.
The tiny gold-tone Saint Laurent logo is only the start of this baseball cap's top-tier details. The bleached denim is a modern neutral for endless styling.
A classic fedora feels brand-new in woven raffia. The scarf tied around the top is a vacation-approved touch.
Surprised to see a bucket hat in a polished tweed fabric? Iro makes the unexpected combination a must-have with a soft-yet-structured shape and quiet logo embroidery.
Go from your workout straight to lunch in this staple. Alo's cap is an athleisure staple that can hold its own beyond the gym.
A blend of two of my favorite things—denim and bucket hats—into one patchy design. It's DIY, but in a cool way.
Visors have made a comeback, especially with racket sports like paddle on the rise. In terry cloth lilac, Lele Sadoughi's take is a grand slam.
This waxed cotton-canvas bucket hat from the Chloé x Barbour collab is suited for all outdoor adventures. It repels water like Barbour's jackets, keeping you nice and dry.
Crochet accessories have recently made waves on fashion's forefront. If you're trying the trend, go the colorful route with Casablanca's vibrant stripes.
Inspired by the baker boy styles of the 1920s, Eugenia Kim's modern version combines leather and a gold-tone chain to reinvent the silhouette.
With the sweetest linen floral ribbon, this raffia visor begs to be packed for the vineyards of Tuscany or the local beach. Your choice.
A denim hat delivers casual edginess to any outfit. Choose from dark-wash or two-toned reworked vintage—either works.
Oversized striped raffia with a leather studded patch? Sign me up for the extra shade.
The color mavens at Ganni delivered an upbeat crocheted hat in time for summer. It's cheerful and bright, making you easy to spot on a crowded beach.
Smith says a leather baseball cap like Apparis' will never go out of style."The simplicity of an all-black baseball cap with an everyday daytime or nighttime look reads fashion forward yet beautifully simple," she explains.
Revisit the '90s in this leather-trimmed cotton-blend hat. The label's iconic anagram makes it identifiably designer in all the best ways.
I had to throw in a beanie, just in case you're traveling somewhere a little less temperate. Isabel Marant's beige merino wool one is a pretty solid (and cozy) select.
Gaby Keiderling is a freelance writer, working on fashion, lifestyle, travel, and sports features.
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