What to Wear at The Kentucky Oaks: The Ultimate Fashion Guide

You’ve got your tickets for Kentucky Oaks, and now the big question: what do you wear? Oaks Day is more than just a race, it’s a celebration of style, confidence, and Southern charm.

Everyone from first-timers to seasoned track regulars wants to look their best, and with a few simple tips, you can make sure your outfit turns heads and feels special.

Let’s make it easy. Here’s everything you need to know about Kentucky Oaks fashion, from your dress to your custom hats, and all the little details that make your look unforgettable.

Quick Answer: What Should You Wear to Kentucky Oaks?

If you want a fast answer, here it is: think bold, think pink. Your outfit should be polished, elegant, and a little daring. Pink is the unofficial color of the day, honoring breast cancer awareness. And remember, hats for women are just as important as your dress.

What Makes Kentucky Oaks Fashion Special?

Kentucky Oaks isn’t just about the horses. It’s a fashion event wrapped in tradition. Held the Friday before the Kentucky Derby, Oaks Day is where Southern style meets high fashion. People come to see and to be seen, so your outfit should make a statement.

There’s no official dress code, but there are a few unwritten rules. If you want to fit in and look your best, follow these simple fashion tips.

Kentucky Oaks Fashion Rules You Should Know

You don’t need a rulebook, but a few guidelines will help you shine:

• Wear Something Pink: Pink is the color of the day. It can be your whole outfit or just a touch like a scarf, shoes, or your kentucky derby hat for women. Pink shows you’re part of the Oaks spirit.

• Choose a Dress That Stands Out: Go for flowy midis, or stylish jumpsuits. Your dress should make you feel confident and comfortable.

• Pick a Hat or Fascinator That’s Bold: This is not the time for a small hat. Go for bold derby hats that catch the eye and add drama to your look.

• Avoid Casualwear: Leave your brunch outfits at home. Oaks Day is about being polished and elegant.

• Skip Fast Fashion: Invest in quality pieces. You want to look timeless, not trendy..

If you’re wondering whether to pick your hat or dress first, it’s a good idea to start with your dress and then match your headpiece for a perfect look. 

Some people like to plan their outfit from the top down starting with a show-stopping hat and building their look around it. Both approaches work, so choose what feels right for you.

Hats vs. Fascinators: What’s the Difference?

Let’s talk about headwear. Your hat or fascinator is the star of your outfit. Here’s how to choose:

• Wide-Brim Hats: Classic, elegant, and always in style. Perfect for a vintage-inspired look.
• Fascinators: Modern, artistic, and a little edgy. Great for a fashion-forward vibe.
• Custom Hats: If you want something unique, go for a handcrafted piece. Custom hats let you express your personality and stand out from the crowd.

How to Pair Your Hat with Your Dress:

• Balance is Key: If your dress is simple, go bold with your hat. If your outfit is already a statement, keep your headpiece refined.
• Coordinate, Don’t Match: Choose complementary colors or textures instead of an exact match.

Pro Tip: Make sure your hat is secure. The wind at Churchill Downs can be strong, and you don’t want to lose your favorite piece.

Shoes That Look Good and Feel Good

You’ll be on your feet all day, so comfort matters. Here are some shoe ideas:

• Wedges: Stylish and practical, they won’t sink into the grass.
• Block Heels: Offer stability and elegance.
• Sculptural Sandals: Add a modern touch to your look.
• Chic Flats: A pointed-toe mule or embellished flat can be just as elegant as heels.

Accessories That Pull Your Look Together

• Minimal but Impactful Jewelry: Statement earrings or a bold ring can elevate your outfit.
• Structured Handbag: A box clutch or mini crossbody keeps things polished.
• Oversized Sunglasses: Vintage-inspired cat-eye or sleek designer frames add a touch of glamour.
• Beauty Musts: A soft, rosy lip, glowing skin, and sharp brows complete your look.

Pro Tip: Bring oil blotting sheets and setting spray to keep your makeup fresh all day.

What to Pack in Your Bag

Here’s a quick checklist for your trackside essentials:

• Tickets and ID: Don’t forget these!
• Sunscreen: Protect your skin from the Kentucky sun.
• Lipstick for Touch-Ups: A vibrant pink or rosy nude that lasts all day.
• Backup Flats: Trust us, your feet will thank you.

Pro Tip: Start shopping at least a month early. The best pieces sell out fast.

How to Shop for the Perfect Kentucky Oaks Outfit

• Start Early: Give yourself time to find the right dress, hat, and accessories.
• Try Everything On: Do a sit-test, wind-test, and comfort check before race day.
• Shop for Quality: Look for pieces that are well-made and timeless.
• Look for Inspiration: Check out the latest top 10 hat trends and other style guides for fresh ideas.

Frequently Asked Questions

Q. What should I wear to the Kentucky Oaks?

A. Wear something pink, a standout dress or jumpsuit, and a bold hat or fascinator. Keep your look polished and elegant.

Q. Do I have to wear pink?

A. Pink is a tradition for Oaks Day, but you don’t have to wear it head-to-toe. Even a small touch of pink is perfect.

Q. Can I wear pants or a jumpsuit to Kentucky Oaks ?

A. Absolutely! Tailored jumpsuits and matching sets are stylish and comfortable.

Q. What kind of hat should I wear?

A. Go for a wide-brim hat, a fascinator, or a custom piece. The bigger and bolder, the better.

Q. How do I keep my hat on in the wind?

A. Use hat pins or a secure headband. Test your hat in a breeze before you leave.

Confidence is the Best Look You Can Wear

Kentucky Oaks fashion is all about feeling confident and having fun. Whether you go for bright pink, bold shapes, or a classic look with a fun twist, the most important thing is to wear it with confidence. This is your chance to shine, make a statement, and enjoy a day of style and celebration.

If you’re looking for a show-stopping hat, The Hat Girls offers exclusive, handcrafted headwear designed to turn heads at Churchill Downs. Check out our collection of custom hats and kentucky derby hats for women to find the perfect piece for your Oaks Day look.

If you want more ideas, see how others plan their perfect Kentucky Derby outfit or explore the latest trends in headwear. The Hat Girls is your go-to source for stylish, high-quality hats that make every event special.

Your Next Step

Ready to make a statement at Kentucky Oaks? Visit The Hat Girls to find your perfect hat and complete your Oaks Day look. 

With a wide selection of hats for women and expert advice, you’ll be ready to step out in style and confidence.