Kentucky Derby Outfits – What to Wear to the Kentucky Derby 2021


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Kentucky Derby Outfits - What to Wear to the Kentucky Derby 2021

Kentucky Derby Outfits – What to Wear to the Kentucky Derby 2021

There’s no denying that the Kentucky Derby is the preppy fashion event of the year. After all, when else do we get the chance to go truly over the top with Southern-influenced patterns, brights, florals, and of course, the hats. No matter if you’re watching the race in Louisville or hosting a Derby-themed party, the key to making the most of any fabulous Derby event is dressing the part.

Here, we’ve rounded up the best tips on how to perfect your ensemble for this year’s Kentucky Derby, along with outfit ideas you can shop now.

Start With Your Kentucky Derby Hat

No Derby outfit is complete without a hat. While wide-brimmed hats are the most popular style, there’s really no limit to how creative your headwear can get. In fact, wearing a hat to the Derby is reportedly good luck, according to the Derby itself. A word of warning, though: the rest of your outfit will likely revolve around your hat, so choose wisely.

We rounded up some hat ideas to shop this year:

Annabelle grosgrain-trimmed straw hat

Eugenia Kim
net-a-porter.com

$465.00

A bold ribbon is an elegant way to dress up a more understated straw hat. 

Pink Kentucky Derby Hat

theoriginaltree
etsy.com

$80.95

But if you’re feeling more daring, the Derby is the perfect opportunity to make a color statement.  

White Derby Hat

TheHatHive
etsy.com

$197.00

Colorful accents can give a neutral-toned hat pizzaz without making too big of a color commitment 

Over Size Rose Hat

LadyHatsBoutique
etsy.com

$118.90

Though classic wide-brimmed hats might be the most common Derby toppers, “understated” is the last thing you’re looking for when it comes to a Derby Day chapeau. Consider race day a chance to really go wild. 

Try a Fascinator

Fascinators—smaller headpieces worn on a headband or a comb—have also become popular at the Derby in recent years, thanks to fans of the British royal family. Many royals, including Kate Middleton and Meghan Markle, have been photographed wearing elegant fascinators through the years, sparking a surge in interest.

Here are a few fascinators to shop for this year’s Derby:

Hurricane Sinamay Ascot Fascinator Hat

Hats By Cressida
amazon.com

$75.00

A cool blue fascinator will no doubt impress. Try this ribbon-inspired version. 

Sinamay Feather Fascinator

Free Yoka
amazon.com

$13.99

This pillbox-style Derby fascinator also features feathers, for a demure look at this year’s race. 

White Fascinator

sophieyounghats
etsy.com

$125.00

A smaller size doesn’t have to mean low drama—take the opportunity to go for some eye-catching height. 

Pillbox Hat with Veil Headband

A petite topper is a great opportunity to go all-out on color and detail.

Opt for Solids for Your Derby Dress

There are two schools of thought regarding Kentucky Derby dresses: some attendees want to let their hats shine, so they choose a simple dress with an understated silhouette and limited embellishment. Others want their dresses to be the main event, so they’ll choose a subtle hat to pair with a brightly colored or patterned dress instead.

If you’re solidly in the solids camp…

Ruffle Sleeveless Body-Con Cocktail Dress

Eliza J
nordstrom.com

$88.80

A ruffle detail at the waist adds just the right amount of interest to this otherwise simple red sheath dress.

Resplendent gathered washed-satin maxi dress

Bondi Born
net-a-porter.com

$1,325.00

The derby is no time to blend in—stand out by combine maximum color with maximum length. 

Lace Sheath Dress

Bardot
nordstrom.com

$129.00

No matter who comes in first, lace is always a winner at the Derby. 

Catalina Fit & Flare Dress

Dress the Population
nordstrom.com

$102.38

A solid-colored fit and flare dress adds some playful flounce and keeps you comfy all through race day. 

Or Opt for a Colorful and Bold Dress

Since the Kentucky Derby is all about channeling your inner Southern Belle, it’s essential to incorporate bright colors, fun florals, or a classic print, like Sarah Hyland did at the 2021 Derby. A bold style is particularly great for a guest who wants their dress to be the conversation starter.

Jamila Midi Dress

Farm Rio
anthropologie.com

$198.00

A punchy pop of prints and colors is just the right vibe for a festive Derby Day. 

Effie Jersey Dress

A mosaic pattern jazzes up an otherwise simple silhouette. 

Kendall Dress

Veronica Beard
shopbop.com

$650.00

A bright pink floral is like a breath from fresh air at the racetrack, or anywhere else for that matter.

The Derby Day Shoe Game

Chic summer sandals, open-toed heels, or chunky pair of espadrilles will do the trick on Derby Day. While the actual Derby race only lasts a few minutes, the day as a whole is quite lengthy, so make sure you’re wearing a comfortable pair of shoes.

Strappy Pointed Toe Mule

Christian Louboutin
nordstrom.com

$695.00

A chic pair of flats that look dressy but won’t torture your feet? No that’s a winning bet. 

Kianna Pump

Louise et Cie
nordstrom.com

$129.95

A delicate lacy pump adds interest without distracting from the rest of your outfit. 

Garavani Rockstud Leather Espadrille Wedge Sandals

Valentino
net-a-porter.com

$795.00

The comfortable and sturdy heels on espadrilles are ideal for anyone at the race track on Derby day. 

Daniella Ankle Strap Sandal

Sam Edelman
nordstrom.com

$99.95

Since you’ll be on your feet throughout Derby day, opt for a block heel to maximize comfort.

The Final Step: Derby Accessories

The final step in your Derby dressing process: accessories. Since the hat and dress are the center of the outfit, keep the accessories to a minimum. Choose simple, subtle jewelry and an easy-to-carry bag that can fit all of your race day essentials. Be mindful of the purse size limit as detailed on the Derby website.

Here are a few accessories to complete your Derby outfit:

Robinson Leather Wallet on a Chain

Tory Burch
nordstrom.com

$298.00

This leather wallet by Tory Burch is big enough to hold the essentials, but small enough to carry around all day while at the race track.  

Freshwater Pearl Huggie Hoop Earrings

Stone and Strand
nordstrom.com

$75.00

Pearls are a timeless choice for Derby Day. 

Lucie leather and straw tote

Kayu
net-a-porter.com

$235.00

A neutral woven woven straw bag is the perfect complement to any Derby outfit, no matter the color. 

Derby Buckle Rope Bracelet

Lagos
nordstrom.com

$350.00

Derby day accessories are all about accentuating, not dominating the rest of your look. A sophisticated sterling silver bracelet with equestrian accents strikes just the right balance. 

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