The hat is the unofficial crown of the Kentucky Derby.

Before the first race is run at Churchill Downs Racetrack , thousands of hats have already made their debut.

Elegant. Bold. Timeless.

But how do you choose the right one?

In this edition of our Kentucky Derby Week 101 Series, we explore one of the most celebrated traditions of Derby culture with two designers who know Derby millinery better than almost anyone.

The Tradition Behind the Derby Hat

At the Kentucky Derby, the hat is never just an accessory — it’s a statement, a tradition, and often the centerpiece of Derby style.

At @Bluegrass Concierge LLC, we are pleased to continue our å Derby Week 101 Series, where we share insights and guidance to help our clients and guests navigate one of the most iconic weeks in sports and hospitality.

In this edition, we explore one of the most celebrated traditions of Derby culture: the hat. From etiquette and styling to emerging trends, few elements define the experience at @Churchill Downs Racetrack quite like the artistry of millinery.

To guide this conversation, we had the pleasure of speaking with Kate Smith and @Rachel Bell Carroll, known as The Hat Girls — featured Kentucky Derby milliners for four consecutive years.

As Featured Milliners of the Kentucky Derby since 2023 and Official Hat Designers of the Kentucky Derby Festival from 2016 to 2024, The Hat Girls have established a reputation for craftsmanship, innovation, and timeless style. Their creations transform millinery into wearable art, offering designs that range from classic Southern elegance to bold statement pieces.

Lifelong friends from Louisville who first met at DuPont Manual High School, Kate and Rachel founded The Hat Girls in 2013 after returning from New York City and Las Vegas. Today, their brand has become a standout name in Derby fashion, helping women elevate their look for the most anticipated weekend of the year.

We hope you enjoy this conversation as much as we did and that it offers helpful insight into Derby hat etiquette, styling, and trends as you prepare for Derby Week.

Interview with The Hat Girls

Tell us more about what it means to be a featured milliner at the Kentucky Derby. What does that recognition represent in terms of craftsmanship and tradition during Derby Week?

Being that the hat is one of the first things people think about when you mention the Kentucky Derby, it couldn’t be more exciting for us to be a part of that long-standing tradition in some way. Partnering with @Churchill Downs Racetrack and the Kentucky Derby has truly been the highlight of our 14-year career; for our business, it’s like making it to the Super Bowl.

Churchill Downs only partners with companies with high standards and prominent brand visibility, so we take it as a very high honor to be included in their circle of sponsors.

How has Derby hat fashion evolved in recent years? Are you seeing meaningful shifts in scale, color, materials, or overall styling?

That’s a tough question! We have definitely shifted to making more fascinators than hats over the years. We’ve realized that women feel those type of headpieces are more functional, typically better for photos, and easy to take off for dinner after a long day at the track.

But on that same note, the longstanding tradition of a big hat still

stands strong — especially with those first-time Derby-goers. They can’t wait to get a large, flamboyant hat on their head!

What trends can we expect to see this year?

Pink is always on trend — that’s probably never going to change.

When designing, we tend to watch the clothes coming off the runway for spring/summer. Those pieces are a big indicator of what the popular colors and styles are going to be for our busy season. Those are the outfits we are going to see over and over when we start collaborating with clients, so that’s always a great insight on what to expect regarding trends.

What are some of the biggest myths or misconceptions about Derby hats? Is bigger always better? Are there unspoken “rules” that aren’t actually rules?

Here’s the thing: we know that a client being comfortable equals confidence.

While some milliners follow the rules of specific hats for face shapes, stature, etc., when it comes to picking a hat we tend to lean more into how the hat makes the client feel when she puts it on.

Does her face light up?

Is she fidgeting with it?

How is she going to feel after a few hours of wearing it?

We like to throw any rules out the window and focus on the confidence the hat brings to the woman — that is our main priority.

Dare to be different and step out of your comfort zone!

How should guests think about selecting hats based on where they are seated? We recently shared insights on reserve seating at Churchill Downs. Does styling differ between 1st Turn Reserve Seating, members-only clubs such as the Turf Club, Matt Winn’s, and private hospitality suites?

How should guests think about selecting hats based on where they are seated? We recently shared insights on reserve seating at Churchill Downs. Does styling differ between 1st Turn Reserve Seating, members-only clubs such as the Turf Club, Matt Winn’s, and private hospitality suites?

While it would certainly help if there was a general etiquette for specific spaces, I think that’s a far-fetched dream. People want to wear what they want to wear and at the end of the day you will see it all at the track.

It is helpful to know that in smaller spaces like a crowded suite or 6-seat boxes, it does help to wear a smaller piece or a more vertical piece (versus a wide-brimmed hat) if you don’t want to bump into people all day long.

Hat vs. fascinator — how should a guest decide? Is it driven by tradition, comfort, scale, or the overall ensemble?

What we’ve realized after years of working with women of all sorts is that comfort is what’s going to drive the final decision. Whether that’s physical comfort or comfort in terms of confidence, at the end of the day you’ll know when you’ve got on the perfect hat.

A lot of our clients going to the Derby for the first time are typically wanting a big hat because of the tradition behind it, but after that first go-round they are willing to try something new and explore the idea of wearing a fascinator.

If a woman is attending the races on both Friday and Saturday, I like to suggest wearing a fascinator to the Oaks and a larger hat to the Derby — that way you’re getting the best of both worlds.

Custom & Luxury Perspective

What should clients consider when commissioning a custom Derby hat? How far in advance should someone begin the bespoke design process?

We start taking custom orders in January, and depending on volume, we typically cut them off around April 1st.

What details truly elevate a hat from stylish to statement-making?

Balance.

You can quickly go from chic to tacky when it comes to Derby hats — you’ve got to balance your use of materials. We also use quality artisan textiles, and that alone makes a huge difference.

You can tell at first glance if a hat is made from quality materials or not, and that to me is what elevates the look of a designer hat.

What advice do you give clients attending Churchill Downs for the first time?

Research.
Look through Pinterest, look through Instagram. Join Facebook groups about the Kentucky Derby. Get an idea of what the weekend looks like through those who have gone before you.
The days are long, and they can be tiring. Being prepared with information beforehand will help you have an idea of what to expect.

And for fun, what is the boldest or most unforgettable Derby hat you’ve ever created?

Making a hat for Simone Biles in 2025 was a highlight of our career. What an amazing, inspiring woman! We were honored to have her wear our hat while she announced “Riders up!” at the Kentucky Derby.

Closing Thoughts

Thank you for trusting @Bluegrass Concierge LLC as your Kentucky Derby concierge and allowing us to be part of your plans. Our goal is not only to assist with the details but to help guide you so you can experience Derby Week with confidence and truly enjoy every moment of this iconic celebration.

Through our Kentucky Derby Week 101 Series, we hope to provide insights that help our readers feel informed rather than overwhelmed as they prepare for the week’s many traditions and events. Our intention is to offer thoughtful guidance so you and your guests can make the choices that best reflect your style and preferences.

In this edition especially, we encourage you to embrace the hat culture that has long been a defining symbol of the Kentucky Derby. Whether timeless, bold, or uniquely personal, the right hat becomes part of the story you carry with you the moment you arrive at Churchill Downs.

To learn more about The Hat Girls and explore their beautiful designs, visit: www.thehatgirls.com to discover their latest collections and ordering options.

Coming Next in the Kentucky Derby 101 Series

Derby Week can feel overwhelming for first-time guests

In our next edition, Navigating Derby Week Logistics, including:  Transportation timing, arrival strategies, race day timing, and private drivers vs ride share

People underestimate this until they attend, and we are here to guide you.Visit us at www.thebluegrassconcierge.com for more information

@Valeria Bentel and @Sandra Downard, Co-founders @Bluegrass Concierge LLC