WHAT TO WEAR

See the latest Derby fashion trends to inspire your look for race day.

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The 2025 Kentucky Derby Style Guide, celebrates a modern blend of timeless elegance and expressive flair with pastel tones, jewel accents, and bold silhouettes.

Designed to inspire fans of all ages, the guide showcases collaborations with guest Style Editor Zanna Roberts Rassi, top fashion partners and milliners, helping attendees craft unforgettable Derby Day looks.

Style Guide 2025

Guest Style Editor: Zanna Roberts Rassi

Fashion, beauty, and entertainment journalist Zanna Roberts Rassi has returned as Guest Style Editor for the publication of the Kentucky Derby Style Guide – overseeing the hand-selected styles that feature a feast of popping colors, new trends, and unique looks which are all elevated by the ever-fabulous headwear. “In designing this year’s Kentucky Derby Style Guide, the vision was to create modern moments that will inspire every Derby fan to dream boldly, embrace or inflate their personal style and craft outfits that are as unforgettable as the race itself,” said Zanna Roberts Rassi. When it comes to the Kentucky Derby – Fashion is my sport (sorry horses)! So, here's some trends we can look forward to seeing come race day – or at your own Derby party.

Zanna's Style Tips

HATS – FIRST.

It’s hats, THEN horses in my book. So my motto is choose your headwear first and then plan your look around it. This is your personality piece. Some trends in headwear…

Cartwheel hats: Exaggerated disc silhouettes. Small crown + wide brim -- lay on the head at an angle. Sculptural. Little mystery, lots of drama.

Ladylike Hats: With smaller pillbox styles dominating both the runway and street style, this will trickle over to race day style with more contained brimless silhouettes and paired down embellishments.

Silver Screen Hollywood: Think Grace Kelly….Veils, headscarves, and turban style hats.

Neutral shades + Big Texture: Gigi Burris talks about her collection as a refined palette of ivory, toffee, and mahogany. Texture and materiality take center stage. Weaves, raffia, and straw.

FASHION

Pastel Palette: The Color(s) of the season, but they're not your average Easter basket variety. These pastels are elevated and fresh with striking silhouettes and unconventional textiles. Reach for a frock in powdery pink, pistachio green or buttery yellow.

Power Peplum: Fret not! While this controversial trend might evoke cringe-worthy memories of skinny jeans, chunky necklaces, and the 2010s – rest assured the peplum in 2025 is all grown up. With a more structured and architectural style (not floppy!!) the peplum feels much more elevated and more FASHION! Opt for a monochromatic color palette or minimalistic design. Peplum tops, dresses with peplum built in.

SHOES

Comfort is of paramount importance. With a long day ahead, the last thing you want is to be tarnished by un-comfy shoes.

Wedge Revival: Wedges in every shape, size, and fabrication. From classic Boho blocky cork wedges to modern metallic sculptural shapes. No matter your style, there's a wedge to suit your look and comfort level.

Woven Shoes: Weave work. Ballet flats, pointy toe, sling-back heels, Mary Janes, multiple color ways… light and airy. Easy to wear for a long day at the races. Openwork weave…. sheer but not working perfectly for the transitional months.

MEN

Monochrome Pastel Palettes: Baby blue, butter yellow, and mint are especially trending. Make it monochrome – head to toe, even the shirt – for major trend points – not to mention ease of styling!

Loosen Up: Double breasted jackets are making a comeback, along with relaxed tailoring.

Men's Brooches: The accessory du jour – the Brooch. Just look at all of Hollywood’s and sports leading men! Metal(s) and jewel(s) like. Gold Roses a la Travis Kelce. Silver feathers a la Coleman Domingo….Brooches are THE trend of the season for men. Consider trading the traditional bowtie for a Brooch.

Men's Hats: Porkpie, fedora, boater are classics – but new to the mix – Newsboy caps and flat caps. For an edgier, less traditional take.

WOMEN

The Kentucky Derby is an event unlike any other and that extends from The Most Exciting Two Minutes in Sports® all the way to the unmatched style. Louisville may not be known as a fashion capital, but the city has a unique style all its own. From Derby hats to bourbon-inspired clothing lines, fashion in Louisville is a blend of Southern charm and urban edge. In the lead up to the Kentucky Oaks and Kentucky Derby, guest come out in their Derby best. Derby week is a chance to show up and show out with men and ladies pulling out all the stops. For some that might mean bold, bright, floral looks and for others it’s a chance to showcase a refined elegance. There are no hard and fast rules when it comes to Derby dressing, in part because what you wear has much to do with where you plan to spend the day. But the same rule goes for everyone in attendance: dress to impress.

Zanna's Picks

: vineyard vines Kentucky Derby Womens Cashmere Rugby Polo Sweater

: Brackish Reins Multi-Bezel Drop Earring

: Radley London Kentucky Derby Small Open Top Grab

OUTFITS

When it comes to picking the perfect Derby Day look, the biggest thing to keep in mind is where you’ll be sitting and what section of Churchill Downs you’ll be taking in the races from. If you’re sitting in an outdoor box, you’ll want something that is chic, fashionable and easy to wear for a day in the sun. The Vineyard Vines Kentucky Derby collection, with its mix of floral print cotton, flirty eyelet and smocked dresses are perfect for a sunny, spring day. The higher up you go in the clubhouse, the dressier the attire. Plan on seeing gorgeous dresses at every turn paired with fascinators and hats to match. Some areas also have specific dress codes, so don’t forget to check before choosing your dress or outfit.

SHOES

Beyond the dress or outfits your shoes can make the biggest statement of your Derby Outfit. Whether you wear heels, flats, or shoes go bold with your footwear. Pro tip: the Kentucky Derby is a long day so do yourself a favor and pack a pair of comfortable shoes or flip-flops to change into during the day.

ACCESSORIES

Compliment your outfit with the perfect wrist accessory. Longines an official partner of the Kentucky Derby has collection of elegant watches that can compliment any outfit you prepare.

The finishing touch to every look, your bag is a very important part of your Derby ensemble. First off, you’ll want to make sure it meets Churchill Downs’ bag policy. Bags should be functional and fashionable with colors that pair with whatever you’re wearing.

HATS

You can’t come to Derby without a hat or fascinator. Well, you can, but where’s the fun in that? The Kentucky Derby is known for its sea of hats.

In the last decade, we’ve seen more ladies opt for fascinators but you’ll still see a wide mix of options. While some opt for feathers and florals, others choose more structured, sculptural pieces -- similar to what you see on British royals. When choosing a hat, make sure it’s something you’ll feel comfortable wearing all day. While the Kentucky Derby race may only be two minutes, the day is a marathon and no matter where you’re sitting, you’ll want to make sure to top off your look with an eye-catching headpiece.

MEN

The modern Derby man possesses an unparalleled color palette to kick-off the spring season. Sun-drenched, tropical colors in bold stripes or busy plaid and bright pastels steal the limelight. Although, if you want a more polished look, a classic navy or seersucker blazer is always in style.

Combines tradition with style with bold pants because it is the eye-catcher from a distance. Pair that with fun shirts where complimentary colors go a long way. Don’t be afraid to incorporate patterns with gingham or striped shirts to add some additional pop.

The jacket is what brings everything together and you can’t go wrong with the classic navy blazer.

Zanna's Picks

: vineyard vines Kentucky Derby Horseshoes Silk Tie

: Brackish Churchill Bow Tie

: vineyard vines Kentucky Derby Bridle Plaid Short Sleeve Cabana Shirt

WATCHES

Compliment your outfit with the perfect wrist accessory. Longines, an official partner of the Kentucky Derby, has collection of elegant watches that can compliment any outfit you prepare.

NECKWEAR

Put everything together with a tie. Most gentlemen wear a necktie, but a bow tie is always a great option. By carefully selecting the right necktie, you can make a lasting impression and be a part of the Derby's timeless elegance and charm.

HATS

Top off your outfit with a hat to complete Kentucky Derby look. Whether you prefer a classic Panama hat, a dapper fedora, or a unique bowler hat, your choice of headwear should reflect your personal style and embrace the Derby’s timeless tradition. So, choose your hat wisely, wear it with confidence, and don’t feel like hats are required. Plenty of people will not have hats as it is all personal preference!

SHOES

When it comes to completing your Derby outfit, selecting the right pair of shoes is just as crucial as choosing the perfect suit and hat. In this blog, we'll explore the best Kentucky Derby shoe styles for men that seamlessly blend tradition, comfort, and sophistication. Whether you prefer classic loafers, wingtips, or more unconventional styles like spectator shoes or velvet slippers, prioritize comfort and quality to ensure you can enjoy the Derby in style. Everyone has their idea of who makes the best ones. The most important thing you need to know is that they should be worn sockless.

MILLINERS

When you hear ‘Kentucky Derby,’ chances are the first things you think of are horses and hats. And there’s a reason for that, it goes without saying that the fashions along the rail are almost as important as the thoroughbreds on the track. On the first Saturday in May, women from all over the world flock to Churchill Downs to show off their best hats and fascinators. But where do these fabulous headpieces come from? The answer for many are the featured Kentucky Derby milliners.

Kentucky Derby milliners are the talented group of designers and makers behind the elaborate and stunning headwear that is a hallmark of the Kentucky Derby. These skilled artisans use their creativity and expertise to design and construct hats and fascinators that are not only beautiful, but also unique pieces of art.

Christine A. Moore

Christine A. Moore, whose designs have been worn by some of the most stylish women at the Kentucky Derby, including Miranda Lambert and Mary J. Blige. Moore, who is based in New York City, started her career as a costume designer before transitioning to millinery. Her designs are known for their elegant and classic aesthetic, as well as their intricate detailing and use of high-quality materials.

Learn More >

Jenny Pfanenstiel

Jenny Pfanenstiel is a unique and talented milliner who crafts fabulous pieces at her studio, Formé Millinery, in Louisville. Pfanenstiel's designs are inspired by her background in dance and theater and often feature bold shapes and vibrant colors. Her hats have been worn by celebrities such as Lady Antebellum's Hillary Scott and actress Angela Bassett. She also regularly partners with Vineyard Vines on a series of pieces to coordinate with their Kentucky Derby collection.

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The Hat Girls

The Hat Girls create pieces are the epitome of chic and sophistication. These fashionable ladies have elevated hat-wearing to an art form, and their creations are the perfect finishing touch to any Derby look. With their keen eye for design and impeccable craftsmanship, wearing one of their pieces will have you standing out from the crowd.

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