Kentucky Derby Style

I am fascinated by derby style. In a world of athleisure, graphic t-shirts and Vans, transporting yourself to a world dominated by fit and flare dresses, perfectly knotted bow ties and headpieces as stunning as they are elaborate is a little slice of sartorial heaven.



I am headed to Atlanta this weekend to celebrate all things girly + derby, kicking off with a friend photo shoot and culminating in boozy brunch, naturally. I have been scouring sites, magazines and event style in order to craft my perfect derby look and am sharing my inspiration with you!

First of all, I attended the Leading Ladies Luncheon last weekend in support of the Daisie Foundation. This derby-inspired fundraiser is helping 250 women receive a well-deserved makeover. Many of these women are cancer survivors, military wives, or have suffered a recent hardship in their lives. I am so proud to have provides styling services for the luncheon fashion show, and will be styling many of these women during their makeover! If you want to get involved, please leave a comment and I will get in touch.

To promote the event, we assembled at the Garfield Conservatory to snap photos in our derby best. You will notice that we all do derby differently- some of us love florals, others lean towards monochorome. Hats and fascinators were provided by Masina Company, the epitome of derby chic headwear.


All photos are by the incredibly talented Rachel Bires Photography!

The Leading Ladies Luncheon was styled by some of my favorite Chicago stylists, including Katie Schuppler and I:


My dress came from Target- you don't need to spend a fortune on derby attire! My headpiece in this photo came from Fox's Designer Off Price, my secret weapon for fabulous pieces.

Here are a few photos from last year's luncheon, with great shots of statement hats and fascinators!

Photography compliments of Rachel Bires.

Still shopping for last minute fascinators and hats? There are TONS available on Amazon Prime that can arrive on your doorstep prior to party time:

https://amzn.to/2joH1iV
Masina & Co. Pink & Orange Derby Fascinator- $38

https://amzn.to/2FzqBNl
Masina & Co Blue & Green Fascinator- $38

https://amzn.to/2HOLF43
Fuchsia Fascinator with Mesh- around $14; various colors available

Pink Petal Fascinator- $24.99

Purple Pillbox Hat- around $11
If you are still looking for an event this weekend, here are some of my favorite Derby Parties around town:

Derby Day Party at the Allium (Four Seasons Chicago)


Dapper dames and gents are asked to don their best Derby attire, especially eye-catching hats, for our Saturday soirée. While watching Derby coverage live, imbibe on mint juleps and bubbles, as well as gourmet bites from our culinary team. May the best horse win!

Saturday, May 5th
2pm-6pm

Day at the Derby benefiting St. Jude's Children's Research Hospital at Old Grounds Social



Join 250+ of Chicago’s floral-clad finest to watch the Kentucky Derby in style. Tickets will include drinks, notably classic mint juleps, appetizers, contest for the most fabulous Derby hats and outfits, Derby-themed game, prizes and a raffle. 

Saturday, May 5 
3-7 p.m.

Derby Day at Arlington Race Track


If you can’t be in the Bluegrass State for the 141st running of the Kentucky Derby, Arlington is throwing the biggest Kentucky Derby party in Chicagoland!   With special all-inclusive packages, fashion contests, and giveaways, it will be a Derby party like no other. Check website for times

Cheers to Mint Juleps, big hats and fabulous fashion! 

Disclosure: This post may contain affiliate links, which means that I may make a small commission if you purchase through my site. It doesn't, however, affect you price. Total win-win. #winning

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