A Quick Guide to Kentucky Derby Outfit Ideas

In 2019, we had the pleasure of attending the Kentucky Derby with vineyard vines. Remember 2019? Lots of travel, large groups as far as the eye could see? Needless to say, I’m so hopeful for the remainder of this year and our hot vax summer ahead. But, I digress… Today, Bob and I are sharing a few Kentucky Derby outfit ideas from the brand. After all, vineyard vines has long been a personal favorite! We seriously wear it all of the time! In fact, 9 times out of 10, you’ll find Bob wearing one of their Shep shirts. Generally, we love embracing the brand’s philosophy: Every day should feel this good, or #EDSFTG.

Anyway, after our experience at Churchill Downs, I walked away completed inspired by the fashion from the day. First, how fascinating are fascinators? I’ve long loved them (as seen on my blog post from the Veuve Clicquot Polo Classic). Also, why don’t we get to wear fascinators more often? Or like… ever. Sure, haute hats and marvelous millinery creations are like an every season occasion for Brits. However, Americans seem to shy away from the haute headpieces!

Kentucky Derby Outfit Ideas

Friends, I absolutely LOVE these Kentucky Derby outfit ideas from vineyard vines. Moreover, vineyard vines is the official style of the Kentucky Derby. Therefore, every year, they release a capsule collection of pieces for both men and women. Some styles are more formal, others are casual.

Women’s Outfit Idea #1: Gingham Dress

First, I chose this gorgeous blue and white floral gingham side-tie dress to pair with this gorgeous white fascinator. Isn’t this fascinator so fabulous? In fact, it’s a handmade piece by Jennifer Pfannenstiel of Forme Millinery, the Featured Milliner of the 147th Kentucky Derby. The fascinator is made in the U.S., and made from strong sinamay, headband and feathers. Also, the price is really fantastic. Trust me, haute headwear like this can get VERY pricey.

Men’s Outfit Idea #1: Gingham Blazer, Mint Julep Tie

Women’s Outfit Idea #2: Navy Floral Dress

Men’s Outfit #2: Navy Blazer with Tan Pants

Women’s Outfit Idea #3: Yellow Ruffle Dress

In Closing

Overall, I hope today’s post sparked some fun fashion concepts for the Big Race. Looking for additional outfit and accessory inspiration and ideas? If so, be sure to checkout this blog post about Kentucky Derby accessories. Also, tell me – have you been to the Kentucky Derby? If so, what did you wear? Also, for more race day fashion inspiration, be sure to checkout my post with LK Bennett about the Royal Ascot.