Domain Registration

Mask? Check. Fancy hat? Check. The must-have fashion advice for Kentucky Derby 2020

  • August 06, 2020

Let’s talk about your fashion for a Kentucky Derby held in September rather than the traditional month of May — and let us not forget we’re in the midst of a public health pandemic.

The runnings of the Kentucky Oaks for fillies and the Kentucky Derby were postponed from May 1-2 to Sept. 4-5 because of the coronavirus outbreak. After consulting with Kentucky Gov. Andy Beshear and local health officials, Churchill Downs announced the races will take place with reduced spectator capacity in general admission, outdoor reserved seating, premium dining and suites.

And while we’re anxiously awaiting for updates on if that will still happen, we thought we’d put together some top fashion tips whether you show up for the races in person or plan to throw a small outdoor socially distanced party at home. Let’s face it, Kentucky Derby weekend in Louisville isn’t just about the horses — it’s an annual fashion event with few rivals.    

The good news — and we all could use a little right now — is that fashion experts say if you already purchased an outfit for May, you don’t need to alter it for September … well, not too much.  

Are face masks the newest way to make a fashion statement?:Here are some unique takes

Sure, you’ll want to add a fabulous face mask to complement your wardrobe — a mask is a must wherever you’re celebrating. And plenty of milliners are making face coverings to match their headpieces for both men and women,including Louisville milliner Kenzie Kapp and Jenny Pfanenstiel and Christine A. Moore, both Featured Millers for the 2020 Kentucky Derby.

Kenzie Kapp models one of her fascinators with a matching face mask for Kentucky Derby 146.  You can reach Kenzie Kapp at her studio at  (502) 771-1286 or email her

Other than a mask, the weather is your biggest consideration.     

“If you are a local, you know that September in Louisville is hot and humid, it’s not like a fall day in New England,” said Jo Ross, a fashion consultant who has been dressing women and men for the Kentucky Derby for decades. “That means you’ll want to dress in garments that breathe so you’ll be comfortable. So think about natural fabrics like cotton, gauze, linen and silk.” 

And guys, if you are wondering if your Seersucker suit will pass the test with fashion police at the end of summer?

“Absolutely yes,” said Ross. “Seersucker suits are a tradition at the Kentucky Derby and were originally designed to be comfortable in heat and humidity.”

In May, there is a Southern Charm that inspires the look at Churchill Downs on Derby weekend and the same will be true when the races are run later this year.  

That means you don’t want to be caught without an elegant hat or fascinator made of lightweight material like straw. Pair your headpiece with a beautiful floral summer dress — an updated and longer hemline will freshen your look at the 146th Kentucky Derby. 

100+ retailers selling face masks online:Athleta, Nordstrom, Anthropologie, and more

Pantsuits with slacks or Bermudas are a playful option in 2020. So are jumpsuits and rompers, Ross said.

“Just be sure you are choosing one in a natural fabric or a blend,” said Ross. “If you are wearing a jumpsuit made out of 100% Polyester, you’ll roast if it’s a very hot day.” 

Models Kristina Russ, Josh Frank, Kasi Shelton and Derrick Clarkson relaxed during a Kentucky Derby fashion shoot with stylist Jo Ross at Churchill Downs. March 11, 2020All merchandise from Von Maur, Oxmoor Center, Louisville, Ky., during a Kentucky Derby fashion shoot with stylist Jo Ross at Churchill Downs. Models from Cosmo Model and Talent Agency.

We’re crazy for color at the Kentucky Derby. As a result, you won’t find many shrinking violets at the track.

Colors hanging in your closet for the race that wasn’t run in May — shades of pink, indigo, orange, bright yellow and gold will still work well in September. 

But if you want to update your color palette, Ross suggests the colors designers have chosen for the fall including caramel, fuchsia, citrine, burgundy, rust and winter whites.  

Last year’s trend of black and white has been replaced this year by navy with a splash of color. And while we’re on the topic of pairing colors, many couples will be coordinating their wardrobes this year.

We’re not talking about matching costumes but rather an elegant and subtle combination of colors and textures. Consider tying your outfits together through accessories like a pocket square and neckwear that blends with the colors in her dress and headpiece. Or complementary or matching face masks.

As for accessories, “shoes and the size of your purse are two things you don’t want to overlook,” said Ross. “Your purse can not be over 12 inches in any direction, it’s a rule of the track but it does give you enough room to throw in a pair of flats or flip flops.” 

Kentucky Derby Day is a long day on your feet, and in the heat and humidity of a sunny September day, you’ll feel it all the way down to your toes if you are wearing stilettos. 

Flip-flops or flats are a must for the walk from the track to your car and trust us, you’ll regret it if you forget this fashion tip.

Finally, and perhaps nearly as important as a face mask this year, be prepared with three wardrobe options because we never know exactly what the weather will dish up on Kentucky Derby Day, no matter what month.  

Thankfully we don’t need to be concerned about snow — which has fallen at some Kentucky Derbys held in May. Heat or rain should be your primary focus in September when a very (very!) early forecast is calling for rain and temperatures in the upper 80s.

“Option one is your dress, pantsuit, jumpsuit or romper,” said Ross. “Option two is adding a shrug or wrap if the forecast calls for morning or evening temperatures to drop — and if you have tickets in an air-conditioned section of the track.”

Dressing for rainy weather should be your third option. Lately, it seems like it always rains on Kentucky Derby Day and sometimes it rains buckets. Be prepared with a clear rain jacket or poncho in your closet. These are great choices because your Kentucky Derby outfit is still visible through the plastic. And remember, no umbrellas are allowed inside Churchill Downs. 

Derrick Clarkson models a cobalt and pastel floral Tallia sport coat, subtle navy plaid vest, raspberry shirt, hand-crafted harwood bow tie, lapel posey, pocket square and straw fedora during a Kentucky Derby fashion shoot with stylist Jo Ross at Churchill Downs. March 11, 2020

One more note on the rainy weather wardrobe. Women may want to have cute coordinating rainboots on hand. Men can now find waterproof versions of their more formal footwear.

Your goal on Kentucky Oaks and Kentucky Derby Day, whether they are held in May or September, is to look like a million bucks, no matter if you’re sitting in the infield or the illustrious Millionaire’s Row. But of course, you can spend much less if you use these tips as inspiration.

It’s true that some women start planning next year’s — hopefully COVID-19 free — Kentucky Derby weekend outfit days after this one is run, but don’t worry if you are just getting started. 

Wear something colorful, comfortable and pretty and you’ll look like a winner.

And don’t forget your mask.

Reach Kirby Adams at or Twitter @kirbylouisville.

Article source:

Related News


Find best hotel offers