The race is on. It’s time to get your gear ready for the 2024 Kentucky Derby!
While the iconic race only lasts a few minutes, the anticipation is always half the fun. Whether you’re lucky enough to be at the track, or attending a celebration, figuring out your unique derby party style is a must.
We are proud to carry a variety of derby-themed outfits that can eaily be worn for any occasion. When we design our styles, we strive for versatile comfort that never looks too casual, yet will help you make a statement at the derby party, the office, or out to a nice dinner.
Below, we’re sharing our best dressy casual derby outfits, complete with on-theme classic pastel color palettes. And a quick note about accessories. The mantra? The bolder, the better. This is the time to be playful with your preppy style. For women, we recommend getting a high-fashion women’s hat or a fun accent piece, like this mint-julep-themed women’s purse. And for men, it’s all about men’s patterned bow-ties with collared shirts, or a men’s boater hat.
Now, let’s show off the styles.
What to Wear To a Dressy Casual Derby Party
Comfortable & Classy Women’s Kentucky Derby Party Styles
Cutter & Buck Virtue Eco Pique Recycled Women’s Polo
If you’re going for more of a dressy casual derby party style, a pristine pastel polo is a safe bet. This sustainable women’s top comes in stunning subtle shades, like baby blue, pale yellow, and this radiant hyacinth. It also has a protective coating to block harmful sun rays, perfect for an outdoor event at a friend's house, or even the race track. Pair this with neutral white or beige pants, or a sleek cardigan.
Polo Features:
- 95% Recycled Polyester, 5% Spandex Pique
- Contains an average of 15 recycled plastic bottles
- UPF 25+ UV Sun Protection
- Moisture-wicking
- Machine wash
Price: $40.00 - Ships free!
Shop the Virtue Eco Pique Recycled Women’s Polo
Cutter & Buck Stretch Oxford Stripe Women’s Long Sleeve Dress Shirt
For a derby party, you can never go wrong with a sophisticated striped women’s Oxford shirt. Roll up the sleeves for a casual look, or pop the collar to embrace the ultimate preppy mode. We love this one for its effortless durability, as it’s crafted with our soft cotton blend and Easy Care fabric. That means no wrinkles, no worries.
Oxford Shirt Features:
- Textured cotton blend stretch fabric
- 64% cotton, 34% polyester, 2% spandex
- Mercerized & wrinkle-free fabric finish
- C&B pennant on inside placket
- Machine wash
Price: $100.00 - Ships free!
Shop the Stretch Oxford Stripe Women’s Long Sleeve Dress Shirt
Cutter & Buck Womens Lakemont Cardigan Sweater
A simple, sleek cardigan with delicate buttons can pull a look together. This smooth women’s sweater is designed with our custom blend of cotton, nylon, and spandex, achieving the right balance of soft and stretchy. If temperatures are chilly, this is a great layering piece over a polo or shirt. And if the sun comes out, you can keep it close by neatly tying it around your waist or neck.
Cardigan Features:
- 80% Cotton 17% Nylon 3% Spandex
- Logo buttons
- Contrast stripe detail at the inside neck
- Contrast color at inside sleeve cuff
- Machine wash
Price: $110.00 - Ships free!
Shop the Women’s Lakemont Cardigan Sweater
Cutter & Buck Pacific Performance Pull On Womens Skort
This women’s skort is the epitome of sporty chic. It’s great to grab for derby day, and truthfully for any outdoor activity, like tennis or pickleball. With its pull-on stretch waistband and knit undershort, you’ll feel secure knowing you can move with ease all day long. In this simple beige shade, you can have fun switching up your Derby style with a bright accessory or top.
Skort Features:
- 86% polyester, 14% spandex Bi-Stretch Twill
- Moisture-wicking
- UPF 50+ UV Sun Protection
- Pull-on stretch waistband and knit undershort
- Machine wash
Price: $100.00 - Ships free!
Shop the Pacific Performance Pull-On Women’s Skort
Versatile & Victorious Men’s Kentucky Derby Party Styles
Cutter & Buck Virtue Eco Pique Botanical Print Recycled Mens Polo
The derby is known for its style statements and its fashionable prints. This botanical patterned men’s polo nails the feeling of luxury without being loud. It’s also made with our ultra-lightweight fabric, meaning you can layer with ease, or rock it on its own if it’s a warm day. This pairs well with bright white pants or shorts, and a fashionable bold belt.
Polo Features:
- 95% Recycled Polyester, 5% Spandex Pique
- Contains an average of 15 recycled plastic bottles
- UPF 25+ UV Sun Protection
- Moisture-wicking
- Machine wash
Price: $60.00 - Ships free!
Shop the Virtue Eco Pique Botanical Print Recycled Mens Polo
Cutter & Buck Stretch Oxford Mens Short Sleeve Dress Shirt
A short-sleeve twist on a timeless Oxford men’s shirt, this is a staple style you’ll want to wear all spring and summer. Built with our breathable textured cotton blend stretch fabric and wrinkle-resistant finish, this material will stay sharp all day. For an elevated look to watch the race, you can throw on a bold blazer, and add a detailed pocket square.
Polo Features:
- 64% cotton, 34% polyester, 2% spandex
- Wrinkle resistant finish
- Textured cotton blend stretch fabric
- C&B pennant on bottom front placket
- Machine wash
Price: $100.00 - Ships free!
Shop the Stretch Oxford Mens Short Sleeve Dress Shirt
Cutter & Buck Men’s Lakemont Sweater Vest
For cooler days at the race track, this men’s sweater vest will add the lightweight touch of warmth you need. With its flattering deep v-neck cut, you can easily throw this over a patterned Oxford shirt. Whatever top you pair this with, make sure to layer with a contrast top of mind. For instance, if you select a neutral vest shade, we recommend picking a bolder pattern or color underneath.
Vest Features:
- 80% Cotton 17% Nylon 3% Spandex
- V neck styling
- Contrast stripe detail at the inside neck
- English shoulder
- Machine Wash Cold Delicate; Lay Flat to Dry
Price: $90.00 - Ships free!
Shop the Men's Lakemont Sweater Vest
Cutter & Buck White Bainbridge Flat Front Short
To complete your derby look, you’ll need bottoms that tie your outfit masterpiece together. For more relaxed Derby parties, especially those outside, we love these crisp men’s white shorts. With maximum pocket storage and stretch, these are the definition of comfortable convenience. Exceptionally versatile with sporty elements, these can easily transition from the derby party to a celebratory round of golf.
Shorts Features:
- The 96% polyester, 4% spandex fabric
- Flat front style
- Front slash pockets and back single-welt pockets
- Clean finished hem
- Machine wash
Price: $95.00 - Ships free!
Shop the Men’s White Bainbridge Flat Front Short
More Kentucky Derby Fashion to Discover
This is just a small look at our endless options for derby party attire. For classic comfort you can count on, we love our lines of men’s polos and women’s polos, which come in dozens of shades, and patterns that will surely make a splash at your race celebrations. We hope the odds are in your favor!
