Going To A Kentucky Derby Party? Here's 13 Winner's Circle-Worthy Inspiration Looks
Let's say the party invite says "casual," yet you show up in an outfit that took days (weeks?) to plan — accessorized to the outermost limits of human comprehension. If this sounds like you, you'll fit right in at The Kentucky Derby or any of the countless Derby parties that occur each year on the first Saturday in May. The famous horse race happens annually at Churchill Downs in Louisville, Kentucky — the big finale of the two-week-long Kentucky Derby Festival.
Not only is it the preeminent horse race, but its history also dates back to 1875. As a result, attendees traditionally get dressed up, with hats as a signature accessory. It's common to see top hats on men and fascinator-style hats on women. The Kentucky Derby is ultimately a horse race — of course — but it's also one of the best excuses to get absolutely over-the-top gussied-up. So, if you're going to a Derby Day party or lucky enough to have tickets to the race itself, we've got some fabulous looks to inspire your Derby style.
Derby style is all about color coordination
Coordination is the name of the game at The Kentucky Derby. Although there's no one dress code, the overall aesthetic relies heavily on color coordination. For example, attendees often match their shoes, jewelry, and hats to one or more colors in their outfits. However, this also applies to your favorite accessory — your date. Couples often plan their styles around a central color scheme, like this cute look @balibbali. The pink and white theme is echoed in her fascinator hat and his gingham shirt, a classic Derby Day pattern.
Gather the girls -- it's twinning time
Dressing for The Kentucky Derby usually goes like this. First, get your besties together and obsessively debate the color scheme. From there, maybe you create an enviable Pinterest board and start pin-pin-pinning to your heart's content. And for the record, this might begin as early as months ahead. One easy way to achieve a seamless group aesthetic is to shop at the same store, as these friends did at That Cute Little Shop. Stores frequently create multiple pieces from the same fabric, making twinning a breeze.
The Kentucky Derby is known for fascinator hats
We're not often invited to an event where a fascinator is the norm. Having said that, if you are, we'd love to be your plus-one. The Kentucky Derby is essentially a fascinator festival, arguably the most popular hat worn at the famous equestrian event. Anything goes with this style of hat; many people make their own or buy a custom one. Crowd favorites range from elegant to kitschy, so let your dreams run wild — from feathers to sequins and beyond.
Show off your preppy prints
One easy way to be sure you and your friends look the part is to look for brands that offer Kentucky Derby collections. For example, Vineyard Vines often offers an annual Derby collection with various complementary patterns and colors. Its preppy perfection matches the Derby mood, especially with the bold colors and prints. Of course, you can always keep the garment classic — like the Pink Eyelet Maxi — and add some statement accessories, like bold earrings and a hat.
Choose a signature color
Almost everyone at your local watch party will be dressed to impress. To stand out, you'll need to have a fashion strategy. One way to go about it is to select a color and then plan your outfit around that. The folks at @himgentlemansboutique featured a pale orange color, perfect for a spring day at Churchill Downs. The couple used the creamsicle-vibe hue for her dress, and his bow tie then balanced that with shades of navy blue and beige. And we love that her fascinator is the exact color of his pants.
The Derby is your chance to wear a birdcage
Yes, honey! This is one of the royal fashion hacks you should start borrowing ASAP — the birdcage veil. Often seen on brides, runways, or for special royal occasions, the birdcage veil is an extremely popular choice for Derby Day looks. The veil itself might be a netted material, as modeled by @kristenmann_manngroup, or any other sheer fabric. It's a fun riff on The Derby's love of headwear and all things millinery-related.
Add a little poppy-powered wow
Here's a prime example of the power of the fascinator. This red look demonstrates how much star power can be channeled through a simple color scheme and extraordinary accessories. The dress itself is a simple, tailored garment, but the fact that it's the exact color of the headpiece gives continuity and drama. Some fascinators are held in place by small hair combs, but this glorious punch of poppy flowers is attached to a simple black headband. So, if you're a DIY diva, you can definitely make your own Kentucky Derby fascinator.
Let Jack Harlow's song be your muse
Of course, we have a Jack Harlow reference. The rapper's hometown is Louisville, the home of the famed Kentucky Derby. Plus, he has a song by the same name. Add to that, the song is featured in this Instagram launch post by Homme + Femme — a moody montage of their new Kentucky Derby collaboration. Its muted pastels and equestrian-themes embroidery channel Derby vibes into cool pieces like old-school cardigans. The line also features a letterman jacket that honors Oliver Lewis, the jockey that won the first Kentucky Derby in 1875.
You're not over the finish line until you accessorize
Although the impossibly tiny handbag is making a comeback, you might opt to size up just a bit once you see these Derby darlings from Radley London. Adding an homage to the very reason the event is happening — horse racing — is a great way to infuse your look with authenticity. The brand's Kentucky Derby Collection features a variety of handbags and leather goods with imagery of horses and roses. It's a low-key statement piece that brings any look over the finish line with style.
Go ahead -- be a frilly filly
Knowing that Derby styles varied widely from preppy to borderline-glam and beyond, there's plenty of wiggle room to explore. @erinkgeary shows up with an enviable frilly filly mood. It's no surprise to find styles infused with romance at an event brimming with rose blooms. We love the soft tulle layers of this off-white dress and how the oversized fascinator includes such a wide variety of feathers. The pro tip here is choosing a neutral dress makes it easy to play with color and texture in the headpiece.
Roses are a part of the Kentucky Derby aesthetic
Roses are everywhere on Derby Day, from the craft cocktail menus to the entryway arches. The theme pays homage to the race's other common name, the Run for the Roses since the winning horse is draped in a blanket of fresh roses. @magnoliamillinery showcases some custom millinery work — a good reminder that hats are often the starting point for putting together a Derby look. Choosing a rose-themed fascinator is a great way for Derby Day newbies to nail the aesthetic.
Pair a floral look with simple sun hat
In a sea of crazy fascinators and birdcage veils, a simple straw hat is an absolute standout. Beyond that, however, @kallista.miller chose a hat that will actually keep the sun out of her eyes during the big race. With this in mind, if you are at Churchill Downs for the live event or an outdoor Derby party, be strategic with what type of headpiece you wear. Miller's post is a reminder that a pretty floral dress and classic straw hat are the perfect race day match.
Look for equestrian themed looks
In the name of whimsical outfits and all things chic, we hereby declare this equestrian-themed look to be a low-key, sizzling-hot Derby look. Bravo to @swoonlafayette for this perfect combination of bold pattern and feminine styling. The horse illustrations usher in nostalgia, perfect for the time-honored traditions of the illustrious horse race. Pair this dress with a navy or pale blue birdcage veil. Or, in a classic Kentucky Derby fashion twist, pair it with something textured, like pink feathered-accented gladiator-style shoes.