What to Wear to Your Derby Party

Stylist Caitlin Fore answers our Kentucky Derby party fashion questions.

Photos by Megan Peters of Crazy Bananas Creative Studio

Few occasions allow you to have as much fun with fashion as the Kentucky Derby, and enthusiasm for the race has spread from Louisville’s Churchill Downs all the way to Kansas City. Thanks to its popularity, you’ll find a host of local events where you can watch the May 7th race, including The Mission Project’s Run for the Roses Kentucky Derby Gala at Lake Quivira Country Club. The event is a critical fundraiser for the organization, which helps adults with disabilities get the support they need to live independently.

In honor of the occasion, Caitlin Fore, Sophisticaited and Town Center fashion blogger and lead stylist of C4 Styling, shares her tips for what to wear to Run for the Roses and other Derby events, shown here on models Shelley Howe, Heather Sanders and Mission Project participant Jon Berry in clothing from Brooks Brothers at Town Center Plaza.

Q: What are the key pieces for men and women when it comes to Derby Day dressing?

A. When it comes to picking out the perfect outfit for The Mission Project’s Run for the Roses Derby gala, it’s all about sass. For men, their attire should be all about the pants! One of my favorite looks for the guys is to wear a printed pair of pants like the pair John is wearing in the fun photos. They are a rustic red and navy blue pattern, and they look great with a classic white shirt and navy blazer. We then finished the look with a crisp fedora, a bright striped tie and a bright blue pocket square and brown belt and shoes. There are a few other pairs of pants I love for men: seersucker and basically any color of the rainbow. The trick is to just keep the rest of the look classic and have fun with the accessories.

When it comes to what the ladies wear to a Derby party, it’s all about the hats and ensuring they coordinate well with the dress. In order to do this perfectly, start with the dress. [To find] the perfect dress for this event, I always go for a silhouette that flatters and feels great. A fun print and/or a bright color is always a great choice. Then I recommend finding a hat or fascinator that compliments or pulls out a color in the dress.

Heather paired her bright pink fascinator and printed pumps with her gingham dress. Shelley wore a gorgeous dress and jacket look and paired it with a perfectly matched fascinator. I loved both of these looks!

Q. What should women keep in mind when shopping for hats or fascinators?

A. Yes! Hats for the ladies are what the Derby parties are all about. I say the bigger the better. But, if big isn’t really your thing, or you have short hair, a fascinator is definitely the way to go. A fascinator can either attach to your hair with a comb or a headband. They are beautiful and a very ornate and fun way to update a dress you already own.

Q. How can other accessories factor into the look?

A. For the gentleman, the best way to have fun with their look is through the ties and pocket squares. It’s a great way to rock a pop of color without going over the top. And the ladies can have a blast with their hats of course, but don’t forget about the shoes and jewelry, too.

Q. Do you have any tips for people who might normally shy away from bold styles, which seem like part of the traditional look?

A. For the gentleman, this is upscale event so come with your best slacks, a white button down shirt and a printed tie. And of course pair it with a dressier belt and shined up leather shoes. If you’re down to wear a jacket, go for it! A classic navy jacket is a great piece to throw on to really finish out the look.

If you are more of a conservative lady and are a little unsure of what to wear, start with your favorite dress. If you have a black dress that is your favorite (because who doesn’t have a LBD), then pick a hat in either a neutral color or a subtle tone. I would then finish the look with classic pearls and nude pumps or sandals.