Dress The Part For Any Kentucky Derby Party

Written By TJ McBride on May 3, 2023
Kentucky Derby Fascinator

The 149th running of the Kentucky Derby is set for May 6th, and that means that most of us, except the lucky few heading to Churchill Downs, will be taking in the race in the next best way: a Derby Day party.

If you’re looking to throw a Kentucky Derby party, or you simply plan on attending someone else’s soiree, there is a laundry list of guidance about how to dress the part. Picking out the correct outfit and hat or fascinator may be just the thing that brings good luck to you and the horse you’re betting.

So, what is the process for picking out an outfit in the Kentucky Derby style? Should one choose their hat or outfit first? How much color is too much? And how formal should you dress?

With so many details to iron out before the Kentucky Derby arrives, PlayTexas is here to help out Derby Day party hosts or just those of us in attendance plan their Derby party look.

 Fashion tips for all Kentucky Derby parties

The sartorial aspect of the Kentucky Derby is one of the cornerstones of the event, whether attending the Kentucky Derby in person or going to a Derby Day party.

The basic approach to a Kentucky Derby party can be broken down into three separate styles depending on how formal the party aims to be. 

The Derby brunch party

The first approach is a brunch-style event with attendees in full Kentucky Derby formal wear. That means pantsuits, cocktail dresses, business formal attire, lots of vibrantly-colored accessories like necklaces, flowers, handkerchiefs, ties and the most important piece of the outfit–the Derby hat or fascinator. 

The brunch-style party, which could be either indoor or outdoor, should most closely mimic the style at Churchill Downs for the actual Kentucky Derby.

Expect masculine outfits to feature warm but light-colored suits, plaid or paisley patterns across the outfit, pinstriped suit jackets, bold stripes and usually a fedora or bowler hat which is worn with comfortable and classy loafers.

Men's Kentucky Derby formal attire

Feminine styles usually revolve around brightly-colored cocktail or sun dresses; clean A-lines, sharp pleats and a Derby hat or fascinator that accents a color in the dress.

Kentucky Derby women's attire
(Photo by Diane Bondareff/Invision for Longines/AP Images)

The Derby garden party

The second option for a Kentucky Derby party would be a semi-formal garden party in a setting with lots of open green space with places to sit in the shade or wander the grounds. A garden party usually entails business casual attire with less flair but still an emphasis on a natty Kentucky Derby hat or a statement fascinator. A garden party places less emphasis on stand-out head-to-toe fashion and more on refined taste and subtle flair.

Classic taste, warm and conservative colors with restrained pop in a sock, shoe or neckwear, along with tasteful and elegantly-understated jewelry mark the sartorial approach of a Derby Garden Party.

The backyard Derby party

The last style of a Kentucky Derby party is a departure from Derby panache. A backyard party where comfort and relaxation while watching the Run For the Roses is the goal. Casual outfits are not only accepted but encouraged at this type of event.

While a backyard Derby Day party may lead some to choose shorts, sneakers and summer barbecue attire for lounging on a chaise and watching the race, one should not drop all formality. A collared shirt is in order and a clean light-colored sneaker or leather sandle and limited accessories. Colorful patterns and prints are again the expectation and stylish sunglasses can elevate an outfit.

That being said, despite the casual attire, no Kentucky Derby party is complete without a Derby hat or fascinator. A common theme in all Derby Day parties, hats and fascinators are always a great choice. 

Choosing a Derby hat or fascinator

Derby hats are quintessential Derby day attire. The Derby hat or fascinator has become as synonymous with the Kentucky Derby as the mint julep. 

Regardless of what style Kentucky Derby party you host or attend, Derby headwear will be a staple of virtually every party goer. A fascinator – which are typically small womens hats that only cover part of the head and are worn at a jaunty angle — has two associations for most people: high-society British weddings and the Kentucky Derby.

When choosing a fascinator, some might wonder which should be chosen first: fascinator or outfit. Sartorial wisdom says to let the outfit dictate the hat. If your Derby outfit is brightly-colored and patterned, choose a desired color in the outfit and find headwear that accents your chosen color. Be careful not to overstate your look here. A bold outfit paired with an equally-bold fascinator can be a distraction.

Kentucky Derby women's hats

If your Derby attire is monochrome and more subtle, feel free to choose more vibrant headwear and use the color wheel to compliment your look.

For a more masculine look, matching a fedora or bowler hat with a tweed or patterned suit jacket is a great combination. Complementing one’s belt with one’s hat band lets the outfit tell a subtle story. Making sure the shoe matches the belt is also a must.

Kentucky Derby men's hats 

No detail is too small

Derby hats and fascinators are the first impression for anyone looking to shine brightly at a Kentucky Derby party, but as this guide indicates, Derby Day parties give many opportunities for self expression. Don’t take any detail for granted. 

If in doubt, just ask yourself: what story will my Derby outfit tell?

TJ McBride Avatar
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TJ McBride

T.J. McBride is a writer and reporter based in Denver, Colorado who covers the Denver Nuggets as a beat writer and the current gaming landscape in Texas. His byline can be found across many websites such as ESPN, FiveThirtyEight, Bleacher Report, and others.

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