Race Day Attire: Kentucky Derby

What to wear for the Kentucky derby

Kentucky Derby & Other Race Day Fashion

Everyone has heard of the Kentucky Derby. It’s the annual horse race where high, fun fashion is paramount. But did you know that there are two additional races that fill out the Triple Crown? The Preakness Stakes and the Belmont Stakes are the two races that follow the Kentucky Derby, and the team that wins all three earns that coveted Triple Crown. You may have heard a bit about the wild traditions that make up Kentucky Derby fashion. Maybe you’ve even attended! But the Preakness Stakes and the Belmont Stakes each have their own dress code. Here, we’ll break it down for you, so you look great at each race.

What to wear for the Kentucky Derby

First, The Kentucky Derby

The Kentucky Derby Theme

The centerpiece of Kentucky Derby fashion is, you guessed it, the hats. Women wear huge Summer hats in bright or pastel colors. The hats feature details such as feathers, buttons, tulle, lace, and more. But at the Kentucky Derby, the men can stand out too.

The Kentucky Derby Look

Make it bold but not too busy

You’ll see all sorts of wild and bold patterns on the gents at the Derby. There are the basics like bold stripes and plaid, but there are also more unique patterns – flamingos, margaritas, American flags, florals, and more. The key to a great Derby look that doesn’t look too busy is to have one element in a bold pattern. For instance, make a bold statement with the shirt, the jacket, or the pants, and keep the other two more neutral. They can still stand out a bit, though. Try a bright or pastel color or a more subtle pattern, but make sure it doesn’t take center stage. 

Add statement accessories

You can also have one of your accessories be in a bold pattern as well: a tie, bowtie, or pocket square. To finish off the look, put on a Panama hat and slip your feet into some horsebit loafers – but forego the socks. 

The goal at the Kentucky Derby is to stand out and make a statement. Derby fashion is definitely the wildest you’ll see in the three races, and it’s tons of fun to get dressed for.

Second, The Preakness Stakes

Fashionable custom suit made to order

The Theme

The Preakness Stakes aren’t nearly as wild and free as the Kentucky Derby, but that doesn’t mean the fashion isn’t fun. Preakness Stakes fashion is a nod to historical fashion – more specifically, the 19th century. You’ll see bowler hats and waistcoats with pocket watches on T-bar chains. Tone wise, you’ll see darker colors with more traditional patterns like houndstooth and tight plaid. Most men wear spectator shoes – low-heeled brogue oxfords, made in two contrasting colors. 

The Preakness Look

Stick to shades of brown, tan, navy, and other darker colors. Your goal is to look as similar to a Victorian gent as possible.

Third, The Belmont Stakes

The Theme

For the final race of the Triple Crown, get decked out in your best Summer gear. Light, breezy, pastel colors are the norm at the Belmont Stakes. Many of the suits are seersucker suits – suits made of a thin, puckered, cotton fabric. They usually have a thin stripe pattern, but can be solid or other mild patterns as well. Whereas the Kentucky Derby is all about going wild with your fashion, the Belmont Stakes is more relaxed and laid-back. 

The Belmont Look

Imagine you’re dressing for a nice party on the water. You can wear thin cotton suits in light, creative colors (usually pastel). The Triple Crown’s bold Derby looks and sophisticated Preakness looks are topped off with mild, cool fashion at the Belmont Stakes.

Pastel suit for belmont stakes
There’s a general theme for Race Day fashion, but each individual race of the Triple Crown has its own style and personality. You want to look race day ready for each of these events, and with this guide, you’ll fit right in. Most importantly, good luck out there. Here’s to hoping the pony you bet on takes home the prize!

Love these tips? Want more?

Book now for a free discovery call with our style experts. We’ll work with you to create a look that is uniquely yours.


Ezra Lambert

Ezra Lambert is a barber and freelance writer. In addition to his work in men’s grooming and lifestyle, he has also written numerous fiction pieces: two screenplays and a YA novel. He lives in San Diego, CA, with his dog, Toni. 

You can order your normal shoe size. Our products run true to size.

Would you like a more precise recommendation? Use the Feetsizr app to measure your feet for the perfect fit.