Jill Courtemanche Millinery

Horse Racing

Fall Racing Inspiration

Horse RacingJill CourtemancheComment

Fall Racing Season is almost here! This year the Breeders’ Cup is happening at Santa Anita Park on November 3rd and 4th and the Bing Crosby Season opens at Del Mar Racetrack on November 10th and runs through December 3rd.

Here is a little outfit inspiration for the season paired with some of our best selling hats and fascinators. Of course, custom is always an option and I would love to work with you to create a custom piece. You can reach out to us here to chat about custom options.

A fun, classic fascinator paired with a bold red lip for maximum impact:

Fascinator: Jasmeen by Jill Courtemanche Millinery

Dress: Cala Pleated Midi by Careste

Bag: Le Coeur Patent Leather Shoulder Bag by ALAÏA

Earrings: Organic Pearl Hoops by Mejuri

Lipstick: Rouge Pur Couture, The Slim Matte Lipstick by Yves Saint Laurent Beauté


Flirty and feminine in classic neutrals:

Hat: Corine by Eggcup for Jill Courtemanche Millinery

Dress: Devi Floral Plunge Mini by Zimmermann

Shoes: Roman Stud Ankle-Strap Wedge Sandals by Valentino Garavani

Bag: Moyen Alice by Clare V.

Earrings: Rose Gold Ball Hook Earrings by Tiffany & Co.


A bold pop of magenta brings this everyday look to life:

Fascinator: Soucoupe by Jill Courtemanche Millinery

Dress: Leilah Dropped-Waist Mini Dress by Cinq à Sept

Shoes: Lizzie Suede Knot Zip Sandals by Bernardo 1946

Bag: Amberley Satchel by Mulberry

Necklace: Zodiaque medal Leonis by Van Cleef & Arpels

Kentucky Derby 2023

Horse RacingJill CourtemancheComment

Our client wearing her custom “Le Profile” hattinator featured in Garden & Gun’s, “Dazzling Hats and More at Churchill Downs”, May 8, 2023 - Photographed by Nerissa Sparkman

The couple of months leading up to the Kentucky Derby is the busiest and most fun time of the year!

For me, Derby Season starts in early January when production begins on new designs and all the ideas I have had percolating in my head start to come to life. I spend time in the fall sourcing new materials and commissioning new hat blocks so I can get to work right after the holidays.

Once the samples are finished, usually around mid-March, I open the studio for custom appointments and begin traveling around the country to do Trunk Shows.

I always encourage clients to bring in the outfit(s) they plan to wear so I can help them choose the perfect style hat, match the colors and tailor the trimmings to their outfit.

The chaos is real and it is always a mad dash to get all of the hats made and shipped in time but I wouldn’t have it any other way.

I love working one on one with clients to create their perfect, custom hat and it’s so fun to receive pictures of clients in their finished “looks” at the track on Derby day and in the weeks following.

Connecting with so many amazing women and getting to be a small part of the fun and joyous occasions in their lives is the best part of what I do!


A few of our favorite custom hat and dress pairings, from left to right: pink and red “Le Profil” hattinator with Lela Rose dress, yellow satin “Dahlia” headband with Simkhai dress, pink and white “Canotier” hat with Lela Rose dress, purple “Contraire” saucer with floral Zimmerman dress, aqua, red and white “Le Profile” hattinator with Edeline Lee outfit, fuchsia and white “Éclat de la Lune” fascinator with Express shoe, “Garden Party Sylvie” hat wit floral Zimmerman dress, natural and red “Le Profile” hattinator with Zhivago dress.


The best part of the whole process is seeing everyone all dressed up and enjoying their day at the track!

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!

Kentucky Derby 2017

Horse RacingJill CourtemancheComment

Hands down, the Kentucky Derby is the busiest time of year here at JCM but also the most exciting! I love making custom pieces and challenging myself to create hats that enhance clients fashion choices while staying true to my design esthetic.

I thought it could be fun to share some pictures and behind the scenes from the lead up to Derby Day or as I like to think of it, the kick off the American Horse Racing Season (it's a long road to Breeder's Cup in November)! 

First we started out doing a fun collaboration with Lou What Wear, a fashion blog based in Louisville. I sent Danielle some hats and she mixed them with her fashion sensibilities to create a series of posts that really enhanced the hats and generated some beautiful photos which you can see below. She also did a nice interview with me that you can read here

Next up I did another collaboration with San Antonio Fashion Blogger and Stylist Kimberly Frick. I have followed Kimberly on social media for a while and inspired by her bright and playful style, I created a special, limited edition collection. We were both excited by the pieces and decided to hold an Instagram contest where we gave away a fascinator for Derby! See Kimberly modeling her hat as well as out Instagram winner, Ashley Grace Johnson of  Texas Fashion Spot in her fascinator on Derby Day below!

The best part of the madness is always seeing clients dressed and ready to go on Derby Day! Wether it is a Derby Party or direct from the track for the Kentucky Oaks or the Kentucky Derby the pictures never disappoint and I love seeing the complete outfits! A huge thank you to everyone who sent me pictures, they really do make me smile!

This year I spent Derby Day at the Ojai Valley Inn and Spa where I had the pleasure of assisting women decorate hats for a Kentucky Derby themed party. It was a really fun event that was beautifully decorated with all best "Run for the Roses" details!   

Time to start thinking about next year...