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Welcome to the Run for the Roses: A Style Guide for the Kentucky Derby

The most exhilarating two minutes in sports is upon us once again, as the 2024 Kentucky Derby gears up to grace the historic Churchill Downs with its timeless spectacle. The first leg of the Triple Crown is a riveting blend of elegance, athleticism, and, of course, unparalleled fashion flair. As hooves thunder down the track, so too does the pulse of anticipation for the finest equine athletes to grace the turf. But let’s not overlook the real stars of the show - the attendees, bedecked in their finest Derby duds - some splashed with a bit of Mint Julep that missed its mark!

man wearing cotton v-neck in preppy style at horse track

The Looks We'll See at The Kentucky Derby

Kentucky Derby fashion is all about one thing: hats. The rest of the look is dictated by the unique headwear that has become (almost) as exciting as the race itself. From the classic Southern elegance to bold avant-garde statements, this year's Derby promises the usual runway of diverse and captivating looks. Expect to see pastel suits paired with vibrant bow ties. Keep an eye out for nods to Southern charm with flowing sundresses adorned with bold floral prints and impeccably tailored blazers paired with crisp white trousers. Whether you're trackside or celebrating from afar, the Kentucky Derby is a showcase of style and sophistication that never fails to captivate the imagination.

man wearing pink dress shirt outside horse track of kentucky derby

Bets to Horse Around With

As always, this year promises to be a showcase of equine excellence. Keep an eye on names like Catching Freedom, Sierra Leone and Fierceness (the current favorite), as they thunder down the home stretch in pursuit of the coveted garland of roses and their share of the record $5M purse!

man wearing all white knit suit for first class kentucky derby look

What You Should Be Wearing

Ah, the perennial question of Derby fashion! For those reveling in the luxury of a VIP suite, nothing less old-money elegant will suffice. Think pastel-hued suits, dapper bow ties, and, of course, the quintessential braided straw hat! We’ve curated a special Trackside Collection for you to impress with.

And for the ladies, it’s all about channeling Southern charm with flowing sundresses adorned with bold floral prints and, of course, a show-stopping hat to top it all off - the bigger the better!

But fear not, even if you find yourself watching the race at your local watering hole, there’s no reason not to dress to impress. Opt for classic Derby attire with a modern twist - perhaps a seersucker suit paired with a vibrant pocket square, or a statement dress in Derby-inspired hues. Remember, it’s all about embodying the spirit of Southern sophistication while adding your own personal flair.

man wearing classic check polo with black slacks for hot weather kentucky derby

About The Collar Newsletter:

Designed to offer a comprehensive and insightful look into the world of elevated man, The Collar provides you with expert advice and thoughtful insights on all the topics you care about. It features a wide range of topics covering everything from lifestyle and fashion to travel and culture. The Collar is a meticulously curated weekly anthology that caters to the refined taste of the modern gentlemen.


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