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A day at the races: How to dress for the Kentucky Derby

Let your colors and patterns fly at the Kentucky Derby

Kentucky Derby Jimmy Garoppolo and Tom Brady

Thanks in no small part to social media, The Kentucky Derby has become more than a horse race, becoming a major annual fashion event. Horse races have historically been social events that encouraged spectators to dawn their most spectacular finery going back to Victorian England. That tradition carried over to the States, and three races of the Triple Crown have been fashion events for America’s upper class for well over a century. As a social engagement, the greatest of the three big races is The Kentucky Derby, and the greatest part of the race is the Kentucky Derby outfits. Churchill Downs Racetrack in Louisville, KY, becomes the fashion capital of the South for one weekend every May.

The rise of social media and “fit” culture have led to a boom in Kentucky Derby parties across the country over the past ten years. An event that used to be a niche interest to horse racing and gambling enthusiasts, along with the few people wealthy enough to attend the event, has become a national fashion event. People who have no interest in horse racing and will probably not even watch the race (there are a series of races happening all day, culminating in the actual headline race) gather together over their shared love of dressing up and partying. It has become an occasion to be seen, both #IRL and on every social media platform.

Kentucky Derby Nontre Davids and Elliott Nichols

The thing about Kentucky Derby parties, as opposed to any other formal attired event, is that the vibe is decidedly Southern. The American South has a very distinct heritage of formalwear, which is celebrated during the Kentucky Derby. This sartorial heritage was influenced by a hot climate before air conditioning. Both fabrics and colors are light; you’ll notice many whites and pastels to fight the heat. Hats are also an essential accessory for both men and women.

They essentially worked as a decorative way to block the sun. We considered these factors and others when assembling this styling guide for The Kentucky Derby. Even if you’re not going to Churchill Downs this Saturday, May 6, you should still dress like you are. You may just be dressing up for fun or doing it for the gram. Heck, you may even genuinely care about the race! Regardless of your intentions, we’ve got everything you need to know here to assemble a monster #DerbyFit.

Kentucky Derb 9 Kentucky Derby official website

Seersucker is king

The most popular suiting fabric for the Kentucky Derby is seersucker. It often comes in a light blue on either cream or white background, but you can find seersucker in pretty much any color. Pink and light green are two great alternatives to traditional blue, and they will help you stand out even more than everyone else at the Downs.

You can go full seersucker suit, or you can just do pants or a jacket. You can even get seersucker shirts, ties, and pocket squares. Just be careful not to overdo it. Stick to the rule of two — if you’re wearing a two-piece suit, no more seersucker. If you do a seersucker tie and pocket square, use a different fabric for everything else.

Todd Snyder White Label Todd Snyder microstripe unconstructed linen sportcoat

All linen everything

If you have ever been to Kentucky in May, you will know why linen is the preferred shirt fabric at the Derby, where you can fry an egg on the concrete you’re standing on. Even if your party is in a cooler climate, linen is still a quintessential part of Derby style. White and light blue are always the safest bets for your shirt because they provide a clean background for your accessories or a detailed suit fabric. If your suit is solid, you can wear a linen shirt with stripes, plaid, gingham, or floral print.

Linen suits are also a staple of Southern fashion. After seersucker, linen is the most common suiting fabric at the races. You can go 100% linen but be aware that you will always have a rumpled look; there is just no avoiding it. If you want a crisper finish, get a linen suit with a cotton, wool, or silk blend. The other fabrics act like scaffolding to keep the linen in place.

A man flaunting a buzz cut, a brownish pair of sunglasses, and a blue button button-down shirt with rolled up sleeves and pink-red floral accents.

Pastels and florals

Derby parties are light-hearted affairs, and the color palette for your outfit should match. Stick to pastels and muted colors. You can mix in navy blue or burgundy for contrast, but avoid earth tones and no black — save for a belt or watchband. This goes for plaids, ginghams, polka dots, stripes, and solids.

Embrace ornate patterns as well. Florals, paisleys, and any detailed print will add pop to your outfit. Feel free to wear elaborately patterned jackets, pants, or even a full suit. Just try to keep things balanced. If your jacket has a strong pattern, go with solid pants and vice versa. If you wear a full suit, keep the shirt and accessories modest.

Man wearing a gingham shirt

Stripes, gingham, and madras

Kentucky Derby fashion relies heavily on classic preppy style, with a healthy dose of bright colors. The three main textures of the preppy warm-weather style are stripes, gingham, and madras plaid. So try to incorporate one of these three as your base texture. You should only use one, though, because the three clash. Shirts and ties are an excellent place to start, but you can find any garment in these textures, from socks to a blazer. Keep the colors light and pick one core color to match all your colors and textures. For example, if you wear navy blue pants, you should have a bit of blue in every other colored texture you wear.

Man wearing khaki suit

Upscale khaki

Khaki can be boring since it tends to be a part of any work dress code. There are plenty of fun ways to wear khakis out there, and you will see them on full display at the Kentucky Derby. If you are wearing a khaki suit, slacks, or blazer, you want to keep it a lighter shade and not too earthy or brown. A good khaki suit is the perfect foundation to have a lot of fun with accessories because khaki matches everything.

Quick style note: Khaki is a color, and chino is a fabric. Chinos can be khaki, but they can also be any other color. A navy blue chino suit is also an excellent choice for a Kentucky Derby party or any other warm-weather event.

Kentucky Derby 8 Kentucky Derby official website

Go in on the accessories

Derby parties are the perfect time to go in on your accessories collection. Always thought about matching your boldest paisley tie with that one floral pocket square but never felt it was the right occasion? This is the right occasion. Once you have your pants, shirt, and jacket picked out, spend some time in front of a mirror mixing and matching accessories. Find the boldest combination that still matches and own it. Derby parties can be loud, stylistically speaking, and having fun with your accessories is the easiest way to not get drowned out.

White Derby shoes

Derby shoes

You can, of course, wear pair of derby shoes to a Kentucky Derby party. The name comes from shoes worn to British horse races, after all. However, you can have more fun with your shoes if you want to. Velvet or knit slippers are great options. Tassal loafers are always a good choice. Any kind of leather slip-on shoe, even an open-backed mule style, will add interesting detail to your outfit.

If you are going to wear derby shoes, it is the ideal occasion to wear white derbies. White derby shoes are a quintessential piece of classic Southern fashion and are perhaps the most appropriate shoe you could possibly wear to celebrate the Kentucky Derby.

man wearing a Kentucky Derby hat

Don’t forget the hat

The enormous decorative hats that women wear to the Kentucky Derby are probably the most famous thing about the race other than the horses. Men wear hats to the Derby too, though. They are predominantly either panama hats or porkpie hats. Both styles are made of straw, which keeps them light and breathable while they keep the sun off your face.

Men have gotten in on the elaborately decorated hats in recent years, but if you’re spending all this effort putting together the perfect derby fit, you should stick to a more modest hat. A simple white or natural straw color with a solid or striped band is best.

The number one rule for styling your Kentucky Derby outfit is to have fun with it! This is a time to wear colors, fabrics, and accessories that you might not normally wear, so don’t be afraid to try something new. The kind of Southern heritage fashion displayed at the derby is flamboyant. From men’s pocket squares to women’s hats, it is all over the top. That eccentricity is what led to the Kentucky Derby becoming a major fashion event on social media. It is an excuse to dress up in a way you probably won’t the other 364 days a year. So above all, we recommend that you go for it, don’t hold back. Just take it easy on the mint juleps; they’re stronger than you think.

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Mark D. McKee
Mark is a full-time freelance writer and men's coach. He spent time as a style consultant and bespoke suit salesman before…
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