If you are one of the lucky ones who managed to obtain a ticket to the biggest horse racing event this year, congratulations! It is a rare opportunity to get to see the Kentucky Derby, and with weeks away from the big day, there are only two things that should be on your mind.
How to make a winning bet, and how to look fabulous on Derby Day.
Since we have TwinSpires to help us make a winning bet, all we need to worry about is our outfit at Churchill Downs. You can find more information about the leading contenders for the event here: twinspires.com/kentuckyderby/odds/
We all know that the Kentucky Derby is less about the race itself and more about the history, prestige, networking, and fashion. So, turning up with your regular casual outfit is out of the question.
But for people who don’t know much about fashion and don’t regularly follow fashion shows, this can make the race more frustrating. With that said, you don’t have to be a fashion guru to nail your Kentucky Derby outfit.
You just have to follow some rules in order to avoid people pointing a finger at you for being over- or underdressed.
Here is what you need to know.
The Hat
It’s weird to start with your hat, but since hats are a big deal for races like the Kentucky Derby, you have to pay close attention. I know that most of you are not familiar with hat styles, at least not the hats that are usually worn at such races. On top of that, men are afraid to wear hats for some reason, maybe it is a step away from their comfort zone.
Choosing the right hat can make or break your outfit. It is also your ticket to standing out, so the bigger the better (just remember not obscure someone’s view of the race).
Ladies should go for a statement piece, such as a fascinator with netting or a full-on sunhat if you want some Old South vibes.
Guys, on the other hand, are not off the hook. They usually go for a fedora or Panama hats, which can make their outfit look even more fashionable. Plus, your hat is the perfect opportunity for you to add a bit of contrast to your outfit.
Dresses and Suits
For women, the Derby’s a dress-up dream. Flowy sundresses in bright florals or bold solids—like coral, turquoise, or lemon yellow—fit the springtime vibe. Midi lengths keep it elegant, but a flirty mini works if you’re in the infield. Tailored jumpsuits are a chic twist—just add heels. Fabrics like linen or cotton beat the May heat, and a light shawl’s clutch for evening chills.
Men, it’s suit time—no jeans allowed in the grandstands. Lightweight seersucker in pastel blues or pinks screams Derby, or go bold with a checkered blazer and crisp white pants.
A three-piece suit with a vest ups the ante—think mint green or lavender for that Southern pop. Skip the black tux; this isn’t a funeral—it’s a party. Tailoring’s key; a fitted cut beats baggy every time.
Shoes
Footwear’s a balancing style versus standing all day. Ladies, block heels or wedges sink less into the grass than stilettos; aim for 2-3 inches in a fun shade like gold or cobalt. Flats—like embellished sandals—work if you’re dancing in the infield.
Guys, loafers in tan or navy keep it sharp without socks (it’s hot!), or polished oxfords if you’re feeling formal. Break them in first—blisters aren’t fashionable.
Bring a backup pair—flip-flops or slip-ons—in your bag. You’ll thank yourself when the ninth race rolls around.
Accessories
Accessories seal the deal. For women, oversized sunglasses—cat-eye or aviators—add glamour and shield your eyes from the sun. A clutch in a bold print (think flamingos or polka dots) holds your julep cash and phone.
Jewelry’s your call—dangly earrings or a chunky necklace, but don’t overdo it; the hat’s the star.
Also, it is important to mention that Churchill Downs has a strict bag policy that you should follow.
Men, a pocket square in a clashing color (say, orange with a blue suit) and a slim tie or bow tie—floral or paisley—tie it together. A lapel pin—horse-shaped, naturally—nods to the day.
Sunglasses work for guys, too—wayfarers or clubmasters—and a watch with a leather strap keeps it dapper without screaming “look at my Rolex.”
Colors and Patterns
The Derby’s no place for muted tones. Embrace spring—lilac, peach, sky blue—or punch it up with emerald or ruby.
Patterns rule: florals for her, plaids or stripes for him. Mix ‘em if you dare—a striped blazer with a floral tie, or a polka-dot dress with a solid hat.
The trick? Keep one piece loud and the rest supportive—too much noise, and you’re a circus, not a fashion plate. White’s a Derby staple, too—crisp and clean, it’s a canvas for bold accents.
Weather-Proofing Your Look
May in Kentucky can flip from sunny to soggy fast. Check the forecast—90 degrees means breathable fabrics; rain calls for a chic umbrella (match it to your outfit) and waterproof shoes.
A light trench or poncho in a fun print saves a suit or dress without killing the vibe. Stash a mini fan or blotting papers—sweat’s not stylish—and a shawl for when the sun dips. Prep beats panic; you want to look cool, not frazzled.
As you can see, it is not that difficult to look fashionable on your next Kentucky Derby visit. So, make sure you have plenty of time to pick the right outfit, just because how you look can affect your overall Kentucky Derby experience.
