19 Stylish Men's Items to Wear to the Kentucky Derby
Whether you're watching the most exciting two minutes in sports at Churchill Downs or at home, here's how to look great doing it.
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What you wear to a sporting event typically tends to be an afterthought... unless you're heading to the Kentucky Derby. The annual horse racing competition is the one day of the year when the outfits are equally as important as the sport. And with the first Saturday of May fast approaching, it couldn't be a better time to start brainstorming your look. From bright and bold sport coats to classic hats and statement accessories, here are a few stylish items for looking your best at Churchill Downs this year.
Vineyard Vines Kentucky Derby Seersucker Blazer
Vineyard Vines Kentucky Derby Seersucker Blazer
If you're shopping Derby outfits, then there's no better place to turn to for that than Vineyard Vines, the Official Style Of The Kentucky Derby. Its 2024 collection, which is filled with tons of stylish duds, like this pinstriped blazer.
Scala Laichow Braid Boater Hat
Scala Laichow Braid Boater Hat
A boater is a classic men's style for the Derby—and be honest, you've always wanted an excuse to wear one.
Vineyard Vines Stretch Breaker Pants
Vineyard Vines Stretch Breaker Pants
When it comes to appropriate derby attire, the brighter the better! These eye-catching salmon trousers from Vineyard Vines is guaranteed to make anyone stand out in a crowd.
Tie Bar Light Blue Duke Floral Bow Tie
Tie Bar Light Blue Duke Floral Bow Tie
Derby day is no time for understated accessories: take a chance on a dramatic print in a small format for major impact without a major commitment.
J.Crew Ludlow Slim-Fit Unstructured Suit Jacket in Irish Cotton-Linen
J.Crew Ludlow Slim-Fit Unstructured Suit Jacket in Irish Cotton-Linen
A breathable linen blazer will leave you feeling as cool as you look.
Jacob Alexander Men's Seersucker Striped Pattern Regular Length Neck Tie
Jacob Alexander Men's Seersucker Striped Pattern Regular Length Neck Tie
Seersucker is the perfect fabric to wear to a breezy outdoor event. Bonus style points for wearing a tie made from seersucker—an unexpected, but classy choice.
Haspel Sapphire Bleau Seersucker Stretch Sport Coat
Haspel Sapphire Bleau Seersucker Stretch Sport Coat
Better yet... why not wear a seersucker suit? Established in New Orleans in 1909, Haspel is responsible for the original seersucker suit—a derby classic.
A straw Panama hat has a classic derby feel (and will help keep the sun out of your eyes during the race).
Tommy Hilfiger Men's Buffalo Tartan Pre-Tied Bow Tie
The Derby is all about bright, bold colors and bow ties—and this one checks all the boxes.
Ties Hold Your Horses Burgundy Tie
Ties Hold Your Horses Burgundy Tie
There is no more appropriate venue for an equestrian tie than the derby.
Vineyard Vines On-The-Go brrrº Gingham Shirt
Vineyard Vines On-The-Go brrrº Gingham Shirt
Pastel gingham is the perfect accompaniment to an iconic mint julep.
Shinesty The Kentucky Secretariat
Bright colors look great when it comes to sport coats. While a brilliantly patterned blazer like this might be a bit much for your average night out, pair it with white linen trousers (or matching pants!), and you will turn heads in the right way at the Downs.
For a true Millionaires Row look, you can't go wrong with a horsebit loafer.
Cufflinks Racing Horses Cufflinks
Wear your love of the races on your sleeve.
David Yurman Petrvs Horse Pinky Ring
David Yurman Petrvs Horse Pinky Ring
A signet ring is an elegant everyday piece, but this horse-emblazoned one is particularly perfect for the Derby.
Cufflinks, Inc. Horseshoe Cuff Links
Cufflinks, Inc. Horseshoe Cuff Links
Make it your lucky day with these lucky horseshoe cufflinks.
If you're going to wear a timepiece, make sure it's one from Longines, the official timekeeper of the Derby.
Todd Snyder x Sanders White Suede Buck
Todd Snyder x Sanders White Suede Buck
A sharp pair of cream oxfords will complement your statement look perfectly.
You'll want to have a prime view of those horses for the most exciting two minutes in sports.
Lauren Hubbard is a freelance writer and Town & Country contributor who covers beauty, shopping, entertainment, travel, home decor, wine, and cocktails.
Sam Dangremond is a Contributing Digital Editor at Town & Country, where he covers men's style, cocktails, travel, and the social scene.
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