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Most Fashionable Hats to Wear to the Kentucky Derby This Year

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The Kentucky Derby might be one of the greatest horse races in the world, but it’s also the height of hat fashion. Whether you’re planning on attending in person, or gathering for a Derby-themed party with friends and family, your headgear is the most important part of your outfit. Here a few of this year’s most fashionable Kentucky Derby hats.

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The Southern Belle

The most traditional look for the Kentucky Derby is a broad-brimmed hat reminiscent of ladies’ extravagant bonnets. Modern hats, however, are a good deal more comfortable to wear! Even with their wide brims, they’re lightweight and come in a huge range of colors and styles. Choose a monochrome hat with minimal decoration for a chic and classic look, or opt for one of this year’s biggest trends: bright color combinations and bold shapes. With so much brim to balance, these hats often come with a little extra help to keep them in place, including adjustable interior sizing or elastic bands that hide beneath your hair. You may need to adjust your hairstyle to best suit the angle at which you plan to wear your hat.

Fascinating Fascinators

Fascinators have been steadily gaining in popularity at the Kentucky Derby. Attached to a headband, or worn with a comb, they’re easy to add to your favorite hairstyle. They’re smaller than traditional Derby hats, but they pack a lot of personality into a little bit of space. Decorated with sinamay ribbons, feathers, and beautiful faux blossoms, there are styles from subtle and understated to extravagant. This year’s most popular looks include oversized flowers made from twists of translucent fabric or feathers, or elegant, swooping geometric shapes that seem to defy gravity as they perch at extreme angles. With less area to work with, fascinators tend to be more monochromatic than traditional hats. Make yours a focal point by choosing a color that accents, rather than coordinates with, your outfit.

A Modern Twist on a Classic Look

Hats are a staple of everyday vintage style, so it makes sense that we see lots of Derby hats that put a fashionable special-occasion spin on these classic looks. One of the most popular is the pillbox. Straight-sided and often embellished with a birdcage veil, this hat combines the dainty size of a contemporary fascinator with vintage elegance, and can be worn even after Derby day. Vintage men’s styles also make an appearance in some of this year’s favorite designs, which feature a fedora-like crown and band paired with a feminine, oversized brim.

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