WHAT TO WEAR

What Should Women Wear to the Kentucky Derby 2026?

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 2026 Kentucky Derby Style Tips for Women

LADIES-TAKE CENTRE STAGE

Tactile Texture

• Fashion as a feeling -- literally and metaphorically. Fringe, Feathers, Lace, embellishments: Textures and tactile finishes on classic silhouettes in dresses, skirts, jackets, pants, and bags.

Main Character Energy

• Prints become as common as neutrals. Florals, stripes, spots. A little retro, a lot of personality.

Crayola Colors

• 110% saturation and pigmentation! Purple, Lime, Orange, Scarlet, Violet.

Skirt Suit

• She’s back and going to be bigger than ever this season and the perfect Derby look! Cropped jackets or blazers with sharp skirts. Pencil or mini. Tweed, floral-embellished. Cropped or high waist. There is a skirt suit to suit everybody.

FEET FIRST! Comfort IS KEY.

• An uncomfortable shoe will ruin your day.

Two Strap heels are always a win-win

• Clean, easy, goes with everything as seen in the style guide. In every iteration. Lucite, Gold, Bright.

Closed Toe Wedges

• Instead of the chunky, think Mules that are sleeker and more modern. Leather, raffia, suede all work.

Two-Tone Capped Toe! À la Chanel. Flats, Mary Janes, Slingbacks, or Kitten heels

Ruched Loafers

• For girls or guys, it's this season's choice of FLAT. Replacing the ballet! Works with a short dress, a long skirt, or a pant — don't question it.

2026 OUTFIT TRENDS

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.

2026 SHOE TRENDS & TIPS

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.

2026 ACCESSORIES TO FINISH YOUR LOOK

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.

2026 HAT TRENDS

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.

What Should Men Wear to the Kentucky Derby 2026?

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 2026 Kentucky Derby Style Tips for Men

FOR THE GENTS

Light but sharp

• Chambray and lighter fabrics, but worn in traditional suiting silhouettes.

Two-tone

• Think a blazer in a popping color and pants in another, like a baby blue jacket with khaki trousers as seen in the style guide. Balance out the statement color of the blazer with a neutral pant.

Hats Matter

• Porkpie, fedora, boater are classics, but Newsboy and flat caps provide a modern edge (JFK Jr.)

Popped & Boxed

• Blazers are always a classic, but collarless cuts, popped collars, funnel necks, or boxy shoulders add subtle style quirks. (MBJ @ The Oscars, Jacob Elordi in Chanel)

2026 WATCHES TO ACCESSORIZE

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.

2026 NECKWEAR TRENDS

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.

2026 HAT & HEADWEAR

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!

2026 SHOES FOR MEN

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.

Learn More >

The Hat Girls

The Hat Girls create headpieces that 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.

Learn More >