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The Beginners Guide To Dressing For The Derby

Photo by Jennifer Ryan Jones

There’s no horsing around when it comes to dressing for the Derby. If you're ponying up for this bucket list event, you'll want to be decked. The Annual Run for the Roses is a great excuse to unleash your more colorful side. Yes, real men do wear pink especially while sipping mint juleps at Churchill Downs. But sporting bright colors isn’t the only way to look like a stud on the infield. Here are our Triple Crown tips for dressing for the derby.

Beat the heat.

The “Fastest two minutes in sports” can feel like an eternity if you’re sweltering in the heat. You can pull a cool (as in not sweating your ass off) look together sans jacket. Button-front shirts made of natural, breathable fabric like cotton and linen will allow air to pass through and dry up the dampness. And a good deodorant will keep sweaty pits at bay. Yes, jackets and blazers are optional when dressing for the derby. But genuinely looking like a million bucks on Millionaire's Row requires channeling your inner Southern gentleman. That starts by wearing a suit or sports jacket, especially, if you have hopes of getting into exclusive spots like The Turf Club where business casual reigns supreme. You’ll be most comfortable if you stick to cotton suitings like seersucker and linen blends.

Brighten Up

Don’t be a horse of a different color. Leave your gloomy black t-shirts and biker denim at home and turn up the wattage of your wardrobe. Dressing for the Kentucky Derby is about sporting pastel pinks and vibrant blues. Have fun with it! Sure, mixing and matching color and patterns can be intimidating, but there’s nothing to be afraid of. The key to trotting around in a bold pattern is to ground it with a solid color. And if you’re with a date, coordinate.

Finish Strong

To be a Derby style standout, you'll need thoroughbred accessories. If you’re a hat guy, and not everybody is, top off your look with a fedora or bowler done in a neutral color. A grosgrain band around the crown is a smart detail. But an entire hat covered in Pepto pink will detract from your otherwise impeccable taste, bless your heart. Yes, you should upgrade your Derby put-together with a colorful bow tie, braided belt, and patterned pocket square. Add a fresh pair of suede bucks, classic monk straps or preppy boat shoes will have you looking sharp for the photo finish.


This article was written and appeared on Grooming Lounge and our Founder, Mike Gilman, were quoted a lot, so we borrowed the article. Giving them credit -- hope it's OK.

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