It’s time to talk about the south’s version of the Super Bowl — the Kentucky Derby. With universal acclaim, it’s a time to celebrate and come fully clad in equestrian-style glamor.
This year, the Kentucky Derby 2023 will take place on Saturday, May 6 at Churchill Downs in Louisville, KY. The left-handed track that spans nearly one and a half miles is soon to house thousands of cheery-eyed fans placing their bets and flashing their hats.
With a wide-open field of 20 horses set to leave the first starting gate at 6:57 p.m. EST, you’ll want to ensure you plan your outfits beforehand — because, at New York Post Shopping, that’s what we’re here for!
Ahead, you’ll find the 15 best Kentucky Derby outfits and hats to sport at this year’s event for both men and women. Think: preppy, Souther-inspired style, from polos and dress pants to statement jewelry and elegant skirts.
While at the stands, shop the best belt bags and crossbody bags to complete your look as well. Off to the races!
Click to jump to a specific category:
- Best Kentucky Derby Outfits & Dresses for Women
- Best Kentucky Derby Outfits for Men
- Best Kentucky Derby Hats
Best Kentucky Derby Outfits & Dresses for Women
1. ANRABESS Kimono Maxi Dress, $45
For an easy-breezy flowy option to cater to all of your Kentucky Derby festivities, shop the ANRABESS Kimono Maxi Dress. With a tie waist and subtle slit, it’s undoubtedly Instagram worthy. Plus, it’s a great Amazon dress for less than $50.
2. BELONGSCI Bell Sleeve Shift Dress, $37, original price: $50
For an option that’s solid-colored and worth your hard-earned coin, the BELONGSCI Bell Sleeve Shift Dress is one we fervently recommend. Specifically, it has more than 46,000 rave reviews, comes in a bunch of colors and boasts a comfortable fit.
3. Lilly Pulitzer Kerrigan Elbow Sleeve Eyelet Dress, $248
When in doubt, wear Lilly Pulitzer to the Kentucky Derby. Though a splurge, the brand’s Kerrigan Elbow Sleeve Eyelet Dress is adorable, perfect for an upcoming formal event and nods to the girly girl aesthetic we all know and love. Also, the bow-tie detail is beyond adorable.
4. Vineyard Vines Derby Flutter Sleeve Smocked Floral Midi Dress, $248
Dubbed the “Derby Flutter Sleeve Smocked Floral Midi Dress,” you can’t pass up Vineyard Vines. In a beautiful floral print, it’s a lovely option to accessorize and wear on the beautiful Kentucky Derby day. Plus, its flutter sleeves make all the difference.
5. Dream Pairs Low-Chunk Block Heel Sandals, $48, original price: $55
As one of the best nude heels we rounded up, the Dream Pairs Low-Chunk Block Heel Sandals are a fairly priced option that you’ll wear on repeat. They boast more than 10,000 positive reviews for their comfortable fit and versatile charm.
Best Kentucky Derby Outfits for Men
1. COOFANDY Linen Cuban Top, $30
You can’t go wrong with a lightweight collared shirt for the Kentucky Derby. Shop the COOFANDY Linen Cuban Top for $30 that pairs well with your finest bottoms for any time of the year. What’s more, it’s great to add to your rotation for summertime dressing.
2. Amazon Essentials Classic-Fit Chino Pant, $20, original price: $25
Amazon Essentials is one of our favorite brands, namely for its affordable price point and feel-good quality. Its Classic-Fit Chino Pant is no different and is now $20 for you to add to you cart. Plus, they have a handsome, flattering look.
For more options, check out our guide to the best men’s chinos.
3. Goofandy Lightweight Sports Coat, $69, original price: $75
For a put-together, preppy look, a quality sports coat will help. The Goofandy Lightweight Sports Coat has more than 8,000 reviews for its high-quality fabric and multitude of shade options, making it an Amazon best-seller. Not to mention, it has a nice slot for a pocket square.
4. Sperry Authentic Original 2-Eye Boat Shoe, $70
Of course, you have to have a pair of Sperry boat shoes in your collection. Nothing nods to the preppy and classic style more and, without a shadow of a doubt, you’ll be rockin’ and rollin’ in these comfortable, handsome shoes all summertime long.
5. Alynn Horse Crew Dress Socks, $17
Yes, we had to mention the Alynn Horse Crew Dress Socks in this guide to dressing for the Kentucky Derby! Whether they’re visible or hidden, this less-than-$20 pair makes things a bit more festive.
For more options, check out our guide to the best men’s socks.
Best Kentucky Derby Hats
1. SAFERIN Organza Derby Hat, $22
We love the SAFERIN Organza Derby Hat that’s less than $25 because it’s a match-all option that isn’t too bold, especially for your first Kentucky Derby. Whether you wear it with a maxi dress or a bodysuit, rest assured you’ll be looking full-glam all day long.
2. FORBUSITE Fascinator Kentucky Derby Hat, $26
Finally — a Kentucky Derby hat that Elle Woods would approve of. In traditional Southern-inspired option, add this bold number to your Amazon cart for a less-than-$30 option that’ll accentuate any hairstyle.
3. Zivyes Kentucky Derby Hat, $29
Audrey Hepburn-inspired and subtly modern, the Zivyes Kentucky Derby Hat is one of our favorites on this list. We love its elegant charm, especially with a pair of hoop earrings.
4. SAFERIN Feather Flower Veil Hat, $18
Talk about making a statement! Shop the SAFERIN Feather Flower Veil Hat for less than $20. If you love all things with a feminine flair, this beige-toned option is one you shouldn’t pass up.
5. Jazmiu Lady Church Kentucky Derby Hat, $29
Navy is a timeless color, and ultra-elegant for the Kentucky Derby. That’s why we love the Jazmiu Lady Church Kentucky Derby Hat that even has a blinged-out appliqué for extra oomph.
Check out the New York Post Shopping section for more content.