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Between the royal wedding and the upcoming Kentucky Derby, it's safe to say that hat season is upon us. We understand the trepidation of donning a headpiece, but when you find the right one, there's nothing more fashionable (remember Jackie Kennedy's pillbox?).

Hats off to these beautiful updates of classic styles:

Fedoras As the leather jackets of hats, fedoras are effortlessly chic (pair one with jeans and a blazer for an instantly cool outfit). Topshop's White Linen Trilby ($45) is perfect for a warm-weather stroll, while the stripes on Swell's Matix Laura Marie fedora ($32) have a fun, downtown vibe.

Birdcage Traditionally worn by brides, birdcage hats are big on vintage charm. We love this delicate satin-bow version by Misaharada ($195), and this bold cocktail hat by British milliner Jane Taylor ($430). Isabella Blow would be oh-so-very proud.

Berets What's a hat story without berets? We like ones with unexpected details, like this playful, printed chapeau by Chatham Girl ($45), and Helene Berman's wool beret with zipper flowers ($75). Both have subtle Parisian flair. 

Kentucky Derby Style We watch the Derby for one reason only--the hats. In our winner's circle: Eugenia Kim's colorful straw hats ($260) and Missoni's vibrant crochet-knit topper ($495). Tune in on May 7 to catch all the fancy headpieces at Churchill Downs.

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