Classic & Bold Styles = Derby

Looking for last minute fashion inspiration for your day at the track or party? Here are some classic and bold looks to help you get started.

“I celebrate Derby each year by making a stop at my best friend’s family home for their annual Derby event. It is definitely a Derby tradition in the Pautsch household, along with attending Oaks each year with friends, drinking mint juleps, and dressing up for the occasion.” – Bailey Wynn, Manager of Lashtastic and owner of Bloomed Roots

Headpieces: Baily is wearing a fascinator (1st image) by Griffin Derby City Hatters and hat by The Hat Doctor.

“There is only one way to do Derby and this is rain or shine! I usually start Derby festivities on Wednesday of Derby week and end on the Sunday after Derby by attending a gala, going to Churchill Downs, a charity event, a brunch and/or day party. (I don’t) shop mainstream so no one looks like me.” – Ashley Payne, Executive Key Account Specialist, Janssen Biotech

Headpieces: Ashley is wearing a fascinator (1st image) by The Hat Doctor and a hat by Attitudes by Angie.

“Since my husband and I got married on Derby Day in 2009, our Derby tradition, when it falls on, or is really close to May 1, is that we go to Ruth’s Chris Steakhouse for dinner and then sneak over to the bar area to catch the race on TV. We beat the crowds, but still get to dress up.” – Allison Hoffer, Bridal Stylist, Laurel Wreath Bridal

Headpieces: Allison is wearing a fascinator (1st image) by Gloriela’s Designs and a hat by Sweet Caroline Hats.

“As a Derby-week tradition for over a decade I attend The Oaks with a group of sister-friends. Our hats have been spotted in pictures and magazines post-Derby, and we bask in this opportunity and tradition to truly Run for the Roses! Recently, we began our celebration early by attending Thurby. It’s just so amazing to us that each day at the track has its own vibe…and we comply.” – Ramona Gray, Owner of GG’s Impressions Fashion Statement and licensed insurance professional

Headpieces: Ramona is wearing a hat by Christine A. Moore Millinery and a fascinator (2nd image) by Sweet Caroline Hats.

“I attend Oaks each year and Thurby. Each year I try to change it up with a different color scheme. Once I’ve chosen a color, then I generally start looking for my outfit. I like to keep my dress simple because I want the focal point to be my fascinator. My best friend Nicole and I plan a full day of shopping for our outfits and headpieces which is really fun.” – Courtney Huff, Co-Founder, and Owner of Triple Crown Social

Headpieces: Courtney is wearing a hat by Dee’s and a fascinator (2nd image) by Designs by Tony.

By Tiffany White and Anita Oldham | Photos by Melissa Donald

Fashion styling by Tiffany White

Hair by Krista Nenni, J Estell Salon | Makeup by Stephanie Jones, Z Salon & Spa

P.S. Thinking of switching up your home decor? Look here for style and gift ideas.