Kentucky Derby Attire & Athletes Who Wore It Best

Every year, the most exciting two minutes in sports has attendees dressed to the nines. Aside from choosing the best race props and picks, deciding your Kentucky Derby attire is the next most important.

The first Saturday in May brings out the best spring wardrobe for men and women. Between big hats, flowy dresses, and an abundance of florals, here’s the fashion you can expect to see in the Churchill Downs clubhouse this season.

If you’re someone who thinks fashion is a waste of time, then carry on following the trend of spending three hours designing your six-leg parlay. But please, be sure to review our how to bet on the Kentucky Derby page carefully – a little help goes a long way.

The Road to the #KyDerby is complete!

Here are your Top 20 horses ⤵️🏇 pic.twitter.com/wtzdtKEtEj
— Kentucky Derby (@KentuckyDerby) April 15, 2023

First Things First, The Tradition Of Kentucky Derby Hats

When someone mentions the Kentucky Derby, the first thing you think of isn’t the horse, but the classic Derby hats. It is the focal point of every woman’s outfit. When the annual event started in the 18th century, founder Col. Meriwether Lewis Clark Jr. wanted to ensure a high-class crowd filled the stands. So, he brought in wealthy women to sip mint julep cocktails and build a colt following.

The wide-brim, extravagantly decorated headwear was a symbol of opulence that women in history would wear on the most special of occasions. The brim, which practically hides your eyes from the sun, is typically filled with flowers, feathers, or ribbon designs. Just like the names of Kentucky Derby horses past and present, creativity is key.

Derby hat tradition suggests, “The bigger the hat, the bigger the luck.” So, if you’re betting on the 2022 odds-on favorite Forte at +325, grab the largest hat you can find to secure your profit.

Me placing my @KentuckyDerby bets after hearing "The bigger the hat, the bigger the luck." pic.twitter.com/7tWQ3RXcV8
— Josie Costigan (@josiecostigan) April 26, 2023

Derby Day Dress Code

The Kentucky Derby style is timeless. It pays homage to vintage British and French vogue, while continuously adapting to modern prints, fits, and trends. Whether you’re in Louisville or stable on your couch at home, here’s how you can dress for the occasion:

For The Fillies

It’s time to channel your inner sweet Southern Belle. Now that you’ve spent 10 to 12 business days designing your hat, you won’t want it to be overshadowed by the rest of your outfit. A preppy, colorful dress is usually the go-to for gals. Floral prints are in-season and on-theme as they watch the colts run for the roses.

Style For The Stallions

Thankfully, guys are finally taking notes and stepping up for the outdoor event. The majority will stick to the basics of a light-colored blazer, dress pants, and tie. But it's becoming more common to see men whip out a tropical or bright and funky patterned blazer. To top it all off, a fedora or bowler's hat compliments the look.

Yay Or Neigh? Celebrity Looks, Some of the Best & some of the Worst

The Kentucky Derby is an exclusive event. So, you can bet your bottom dollar that the richest and most popular faces are found in the crowd of 150,000. Here are some of the best and worst looks in recent years:

Best: Joey Fatone

He's attended over 20 Kentucky Derby races and has quickly become a fashion fan favorite. The former NSYNC member doesn't shy away from attention-grabbing suits. If there's one bet that is a lock, it's that Fatone will be best-dressed again this year.

Worst: Tom Brady

The seven-time Super Bowl champ has been spotted on the grounds a few years and truthfully, has missed the fashion mark at all of them.

Tom Brady channeling some looks at the Kentucky Derby. pic.twitter.com/zu607ICoer
— Tim O'Brien (@TimOBrien) May 3, 2021

Best: Bianca Belair & Montez Ford

The WWE stars stunned the carpet with this look. The cohesion between Ford's suit and Belair's accessories is perfect. Belair went above and beyond with her Derby hat, decking it out in roses.

.@WWE superstars Bianca Belair and Montez Ford pic.twitter.com/O7lQhAPT0D
— Andrew Henderson (@andrwfhenderson) May 7, 2022

Worst: Will Levis

I would expect a little more from the Kentucky QB, who has admitted to putting mayo in his coffee and chomping a banana with the peel on ahead of the NFL Draft.

.@UKFootball quarterback Will Levis says they’re “gonna kick some ass” this upcoming season pic.twitter.com/7NUheIakxH
— Andrew Henderson (@andrwfhenderson) May 7, 2022

Best: The 2019 Green Bay Packers

The boys stepped off the field and headed to the Churchill Downs grounds dripping in style. Aaron Rodgers looks sharp in his beige monochromatic look.