Stylish Kentucky Derby Outfit Ideas for Men

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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.

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.

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.

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.

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.

Ludlow Slim-Fit Unstructured Suit Jacket in Irish Cotton-Linen

A breathable linen blazer will leave you feeling as cool as you look.

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.

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.

Toyo Safari Hat

A straw Panama hat has a classic derby feel (and will help keep the sun out of your eyes during the race).

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.

Hold Your Horses Burgundy Tie

There is no more appropriate venue for an equestrian tie than the derby.

On-The-Go brrrº Gingham Shirt

Pastel gingham is the perfect accompaniment to an iconic mint julep.

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.

Jordaan Leather Loafer

For a true Millionaires Row look, you can't go wrong with a horsebit loafer.

Racing Horses Cufflinks

Wear your love of the races on your sleeve.

Petrvs Horse Pinky Ring

A signet ring is an elegant everyday piece, but this horse-emblazoned one is particularly perfect for the Derby.

Horseshoe Cuff Links

Make it your lucky day with these lucky horseshoe cufflinks.

The Longines Master Collection GMT

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

A sharp pair of cream oxfords will complement your statement look perfectly.

Round Sunglasses

You'll want to have a prime view of those horses for the most exciting two minutes in sports.

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