Kentucky Derby-Inspired Fashions

By: clothing, Fashion, Cocktail, The Look, Berks County, May 2023

The Kentucky Derby is May 6. Even if you’re not planning a road trip, you can host a race-themed party. Dressing up — and wearing hats — has been a pivotal part of this landmark event since the first race in 1875. Check out these options and showcase your own Derby-inspired ensemble.

1. Sublime Sinamay.

Channel iconic Derby style with this wide-brimmed hat. Made of breezy sinamay, a cluster of feathery trim adds to the fun. The natural hue can be paired with a variety of colorful solid or patterned dresses for a stunning look.

August Hat Company Sinamay Ladies Hat, ticketed $168, sale $84, Boscov’s

2. Spring Sensation.

Celebrate the warm weather and show off your shoulders. This sleeveless dress features a ruffled hem, elegant fabric buttons and a belt to highlight your waist. The floral pattern includes a range of blue hues with spring-green and silver accents.

MSK Sleeveless Dress, ticketed $70, sale $39.99, Boscov’s

3. Vintage Allure.

Choose a vintage hat for one-of-a-kind appeal. This broad-brimmed pick is a delightful lemon yellow with a cascading tie in the back. Pair it with a complementary hue like blue or purple, or go all yellow for monochromatic style.

Vintage women's 1950-60s wide brim hat, $28, etsy.com/shop/ vintagerose1234

4. Bold and Bright.

Vibrant colors are a popular derby choice. Designed in collaboration with O, The Oprah Magazine, this dress combines purple and green atop a bold silhouetted pattern. Bask sleeveless in the sunshine, or layer up with a cardi on cooler days.

Talbots Oprah Collection Floral Dress, Size 6, $24.99, From The Heart Consignment Shop

5. Elegant Lace.

Classic neutrals create a graceful vibe, and are ideal for pairing with a variety of striking hats or fascinators. Cream-colored lace gives this dress a subtle, airy texture and the black accents will emphasize your waist, bust and shoulders. LOFT Lace Dress, 10P, $16.99, From The Heart Consignment Shop

LOFT Lace Dress, 10P, $16.99, From The Heart Consignment Shop

6. Sophisticated Style.

Stay cool and sun protected with a timeless fedora. Toyo straw is made from shellacked rice paper for a lightweight refined look. Wear this hat with a sports jacket or a seersucker suit for the ultimate in cool elegance.

Men’s Scala Toyo Straw Fedora, ticketed $50, sale $24.99, Boscov’s

7. Casually Stated.

Take a break from formal attire and demonstrate your Derby fandom. Off track, wear this soft, cozy tee with your favorite distressed denim and bright sneakers. Made by a woman-owned company, “Talk Derby to Me” is screen printed by hand.

Moonlight Makers “Talk Derby to Me” tee, $15, The Boutique at J. Nolan

8. Fascinating History.

Go vintage with this 1950s fascinator. This piece stays in place with a celluloid hair clip. The black velvet bow is paired with a cascade of flowers. Black netting extends midway down your face to create an air of mystery.

Vintage 1950s Women’s Headpiece, $18, etsy.com/shop/vintagerose1234

9. Classy Cocktail.

If you prefer mid-size headwear, consider a cocktail hat. This vintage version features one bountiful bloom accompanied by a cluster of smaller flowers on the other side. Made in the 1950s, this hat is topped with netting for extra drama.

Vintage 1950s Women's Cocktail Hat, $28, etsy.com/shop/vintagerose1234

10. Confident Classic.

Top off your outfit with flair. Handmade in Italy, this straw boater is accented by a vibrant red and blue band. Make it your go-to accessory for formal warm-weather outfits. Wear with a bow-tie and blazer for a debonair ensemble.

Zakira Straw Boater, $50, The Boutique at J. Nolan

11. Dapper Choice.

Stand out from the crowd. Bow ties are popular derby accessories, and a great way to put a fun, preppy spin on your outfit. With its vivid red color and whimsical horse-themed print, this one’s perfect for race day.

Alynn Photo Finish Bow Tie, $28, The Boutique at J. Nolan

12. Winning Accessories.

Celebrate the day with race-themed earrings. These eye-catching, handmade designs will ensure your hat doesn’t get all the attention. Choose from checkered flags or spirited horses. Combine with a bright solid-colored dress and add a fanciful touch to your ensemble.

Handmade Derby Earrings, $25, The Boutique at J. Nolan

13. Feathered Glamour.

Make a big style statement with a hat alternative. This fascinator stays in place like a headband and includes feathers and netting for bold style. Besides Derby-themed events, this royally inspired headwear is a perfect choice to wear at a wedding.

August Hat Company Fascinator, ticketed $68, sale $34, Boscov’s

14. Royal Favorite.

Choose polka dots for a chic, playful look. This navy and white dress keeps things cool with cap sleeves and side ruffles. Polka dots are one of Kate Middleton’s favorite patterns, and are ideal for looking stylish at racing and sporting events.

Tommy Hilfiger Navy/Polka Dot Dress, NWT, Size 6, $24.99, From The Heart Consignment Shop

15. Fabulous Flowers.

Take center stage with a breathtaking floral pattern. A dazzling mix of reds, pinks and yellow roses gives this dress a summery feel. Wear it with strappy sandals, a colorful bag and a flower-adorned hat for a fresh, chic look.

Fashion Nova Floral Strapless Dress, Size 2X, $12.99, From The Heart Consignment Shop