A complete guide for women and men on what to wear for Derby
Big hats and bow ties- half the fun of Derby is picking what to wear! Like Carnival across the world, this is one big dress up party. Some sections have dress codes, but for those of us not flying on private jets, it’s wide open. Here’s a few tips for everyone on what to wear for that fabulous outfit to the Kentucky Derby.
Think pink for Friday at the Derby
Friday is Oaks Day and it draws a large and stylish crowd just like Derby Day. Friday celebrates the ladies, both equine and human and as such Churchill Downs decks itself in pink. Almost everyone, of every gender, wears some pink in honor of the big filly (young female) race and the breast cancer awareness walk . Don’t be a humbug. Get your pink on.
Go for it- there is only one Kentucky Derby
While some will be in shorts and tees, almost everyone dresses up. This is not your typical dress event; this is your chance to wear any sort of formal flair you can imagine and be admired. You can be wild and eccentric or beautifully classic, but it’s hard to overdress at Churchill Downs. If you want to try something, go for it. The general rule is the cheaper your tickets are, the more outlandish you can be. The infield crowd always brings the humor.
Comfy shoes are a must have
Women, bring flats. Some drunken high school and college-age girls don’t follow this rule and end up limping on scudzy, sore, bare feet through broken glass and 150,000 people’s mess. Don’t learn the hard way that there is a lot of walking and standing and often through mud and trash. It’s a time-honored tradition to wear your flats to the Downs, change into your heels once there, and later slip your flats on again. After standing in the rain for 8 hours this last time, I would also recommend for everyone shoes that won’t be ruined by standing water.
Bright and fun wins the day
Cheery colors. Bold patterns. Florals. Seersucker. Big, full skirts. Southern. If you look like you might have copied the Vineyard Vines color palette, you’re good. This is not the time for your black tie wedding couture or the sleek and mod look. Actually, it’s Derby so you can do whatever, but most will be living large in color.
Let’s talk hats and fascinators
You must wear a hat to the Kentucky Derby, darling. Whether you pick the dress or the hat first, find your favorite and build around it. You can match outright or use the color wheel for complementary colors. Some say Churchill Downs is for the traditional big hats, and not for fascinators (fascinator: think Princess Kate hats, elaborate feathers and ribbon on headbands.) Fascinators tend to be a third of the price, however, so you may opt for that over the hat and you definitely won’t be the only one. Etsy is a gold mine for affordable options for both and many sellers custom make to your colors. Stein Mart and similar stores often will have cheaper, quality hats without the feathers and flowers. If you want to get bold, buy a base and then your own sinamay ribbon, flowers and feathers and make your own! Men get in on the hat action too: fedoras, driving caps and panama jack hats are winners.
Ties and pocket squares
Men, feel free to wear a hat for the Kentucky Derby, but first nail your tie and pocket square. Horse racing has forced me to learn more about the art of choosing pocket squares and ties. Top rule: you don’t want your pocket square to match the tie. True at all times but only becomes relevant for many at Derby. No matchy-matchy. Instead you go for complementary colors with varied patterns. (Complementary colors: colors opposite each other on the color wheel. Colors next to each other on the wheel are also acceptable.) Consider your suit’s color when choosing the tie and square for contrast. The fold of the pocket square is important and there are many options.
Don’t forget to dress for the weather
Rain or shine, the Derby has never rescheduled in its hundred plus years of history. This past year it rained for 8 hours straight. Literally. It was a record for Derby day. Churchill Downs does not allow umbrellas. Even if you snuck one in, the crowd would riot. It simply isn’t done. Bring ponchos, lots of ponchos, and buy them ahead of time. The 97 cent poncho at Walmart is just as good as the $5 one sold at the track. Ponchos for you, for your bags, for your legs, to cover your seat. Ponchos, ponchos, ponchos. I even saw some clever people that had Ziploc baggies for their phones and racing programs. (I rued not having one when my phone told me its USB was wet and it was seriously considering saying goodbye.) Also, buy a cheap plastic cover for an expensive hat.
Cold happens; it is the first weekend of May in Kentucky. Be thoughtful and prepared with some outfit additions/changes. Think about if your outfit might be ruined with weather. If you’re not prepared and important things are getting soggy, be prepared to hang out under the grandstand, or say screw it and down a drink. And bring some sunblock because if you’re lucky, the sun will be blazing down
Whatever you decide, just wear it with confidence and enjoy the spectacle of all the people watching!
May the road rise to meet you, travelers, and may you be wearing seersucker.
(Down and Derby: get more tips on getting tickets, lodging, transportation, and navigating the big day in the rest of the Down and Derby series.)
