Jill Courtemanche Millinery

derby fashion

A Look Back at Kentucky Derby 2019

Horse RacingJill CourtemancheComment

I thought it would be fun to revisit some of last year’s Kentucky Derby fashion as this weekend will bring the running of the rescheduled 2020 Kentucky Derby without spectators. The 2019 Derby was our busiest season ever! In addition to doing Trunk Shows around the country, we had the opportunity to outfit and an entire corporate event of 20 couples which made for a fun fashion challenge.

When it comes to choosing a Derby hat, a daring few choose their hats before the outfit but most women (and men) usually choose their outfits first and bring them when they come to choose a hat. To start, we have you try on lots of different hat silhouettes to narrow down what you like and what best suits the shape of your face. From there we choose the type of fabric, and the best colors and trim to match your outfit. This customization process is what really make our hats unique and often times results in a one-of-a-kind creation.

Here are a few dress and hat combos:

From left to right: Lela Rose dress with custom “Le Portrait” hat, White House Black market dress with custom “Nouvelle Lune” fascinator, Vineyard Vines dress with custom “Jolie Femme” hat, Eliza J dress with custom “L’evier de la Cuisine” hat, Dolce & Gabbana dress with custom “Soucoupe” fascinator, red and white printed dress with custom “Jolie Femme” hat, Chiara Boni dress with custom “Plateau Composé” hattinator, purple eyelet dress with custom “Dramatique” hattinator, Trina Turk dress with custom “Flirter” fascinator, Frank Lyman Design dress with custom “Le Melon” hat.


I really love bringing these fun pieces to life and adding the special touches that make each hat unique. The best part of Derby Season is when I get to see everyone in their looks at the track and I am very grateful that so many clients shared their pictures with me, which means I get to share them with you!