17 Best Pink Dresses to Wear to the Kentucky Oaks

kentucky oaks pink dresses
The Best Pink Dresses to Wear to the Kentucky Oaks


"Hearst Magazines and Yahoo may earn commission or revenue on some items through these links."

The Kentucky Derby isn't the only big horse racing event that takes place at Churchill Downs the first weekend of May. The Kentucky Oaks, a premiere race for 3-year-old fillies (or female horses), is held the day before, and is another exciting opportunity for racegoers to show up and show out their outfits.

Like the Derby, the Oaks also has a very specific dress code. Racegoers are encouraged to wear pink in honor of the race's official flower, the stargazer lily, and in support of breast and ovarian cancer. And for some, the stakes are even higher off the race track, with the annual Kentucky Oaks Fashion Contest (the best-dressed winner takes home a Longines timepiece).

If you're heading to Louisville for Derby weekend, or planning a celebration at home, now is the time to start your shopping. Ahead, we rounded up some of the prettiest and first-place worthy pink dresses to wear to the Kentucky Oaks this year. Just don't forget your hat or fascinator!

Kentucky Derby Strappy Maxi Dress

Perfect for the Oaks, seaside sips, and summer weddings, this bold one-shouldered number is a style you'll wear again and again all season long.

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fwww.vineyardvines.com%2Fproduct%2Fwomens-dresses%2Fkentucky-derby-strappy-maxi-dress%2F2Q011377.html&sref=https%3A%2F%2Fwww.townandcountrymag.com%2Fstyle%2Ffashion-trends%2Fg46934515%2Fbest-kentucky-oaks-pink-dresses%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link rapid-noclick-resp">Shop Now</a></p><p>Kentucky Derby Strappy Maxi Dress</p><p>vineyardvines.com</p><p>$268.00</p>

Lilly Pulitzer x Badgley Mischka Honor Ruffle Dress

Derby weekend isn't the time to blend in. Make a statement with a ruffle dress.

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fwww.lillypulitzer.com%2Flilly-pulitzer-x-badgley-mischka-honor-ruffle-dress%2F015999.html&sref=https%3A%2F%2Fwww.townandcountrymag.com%2Fstyle%2Ffashion-trends%2Fg46934515%2Fbest-kentucky-oaks-pink-dresses%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link rapid-noclick-resp">Shop Now</a></p><p>Lilly Pulitzer x Badgley Mischka Honor Ruffle Dress</p><p>lillypulitzer.com</p><p>$585.00</p>

Florence Strapless Lace Applique Midi Dress

Between the lace appliqué details and the subtle hint of sequins, this strapless number is lovely as can be.

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fwww.neimanmarcus.com%2Fp%2Fhelsi-florence-strapless-lace-applique-midi-dress-prod268220303&sref=https%3A%2F%2Fwww.townandcountrymag.com%2Fstyle%2Ffashion-trends%2Fg46934515%2Fbest-kentucky-oaks-pink-dresses%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link rapid-noclick-resp">Shop Now</a></p><p>Florence Strapless Lace Applique Midi Dress</p><p>neimanmarcus.com</p><p>$575.00</p>

Tiffany One-Shoulder Midi Dress in Sky

Oaks Day is the perfect chance to give Barbiecore for a spin if you haven't already.

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fwww.nordstrom.com%2Fs%2F5064746&sref=https%3A%2F%2Fwww.townandcountrymag.com%2Fstyle%2Ffashion-trends%2Fg46934515%2Fbest-kentucky-oaks-pink-dresses%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link rapid-noclick-resp">Shop Now</a></p><p>Tiffany One-Shoulder Midi Dress in Sky</p><p>nordstrom.com</p><p>$111.00</p>

Gia Beaded Shawl-Embellished Dress

If you want to make maximum impact, might we suggest this hot pink dress finished with a semi-sheer shawl-inspired bodice with beaded blooms? Understated, but you won't go unnoticed.

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fwww.saksfifthavenue.com%2Fproduct%2FTheia-Gia-Beaded-Shawl-Embellished-Dress-0400018530723.html&sref=https%3A%2F%2Fwww.townandcountrymag.com%2Fstyle%2Ffashion-trends%2Fg46934515%2Fbest-kentucky-oaks-pink-dresses%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link rapid-noclick-resp">Shop Now</a></p><p>Gia Beaded Shawl-Embellished Dress</p><p>saksfifthavenue.com</p><p>$645.00</p>

Lily Ruched & Ruffled Stretch Midi Dress

Stretchy ruching offers a comfortable and flattering fit, while the tiered ruffles add an oomph of playfulness to this otherwise sophisticated number.

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fwww.anthropologie.com%2Fshop%2Fv-chapman-lily-ruched-ruffled-stretch-midi-dress&sref=https%3A%2F%2Fwww.townandcountrymag.com%2Fstyle%2Ffashion-trends%2Fg46934515%2Fbest-kentucky-oaks-pink-dresses%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link rapid-noclick-resp">Shop Now</a></p><p>Lily Ruched & Ruffled Stretch Midi Dress</p><p>anthropologie.com</p><p>$365.00</p>

Elle Sweetheart Neck Sheath Midi Dress

Sure, this dress is simple, but when paired with a show-stopping fascinator and statement accessories? You'll have a winning Oaks look.

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fwww.nordstrom.com%2Fs%2F5532926&sref=https%3A%2F%2Fwww.townandcountrymag.com%2Fstyle%2Ffashion-trends%2Fg46934515%2Fbest-kentucky-oaks-pink-dresses%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link rapid-noclick-resp">Shop Now</a></p><p>Elle Sweetheart Neck Sheath Midi Dress</p><p>nordstrom.com</p><p>$168.00</p>

Scarlett Side-Bow A-Line Midi Dress

If you're going to go all out, make sure you do so in a shocking pink midi topped with an oversize bow.

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fwww.anthropologie.com%2Fshop%2Fsachin-babi-scarlett-side-bow-a-line-midi-dress&sref=https%3A%2F%2Fwww.townandcountrymag.com%2Fstyle%2Ffashion-trends%2Fg46934515%2Fbest-kentucky-oaks-pink-dresses%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link rapid-noclick-resp">Shop Now</a></p><p>Scarlett Side-Bow A-Line Midi Dress</p><p>anthropologie.com</p><p>$298.00</p>

Oh Oh Livia's Strapless Gingham Midi Dress

A breezy seersuckerd strapless dress featuring a pretty plaid print? It's like Rosie Assoulin designed it just for the Oaks.

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fwww.modaoperandi.com%2Fwomen%2Fp%2Frosie-assoulin%2Foh-oh-livia-s-strapless-gingham-midi-dress%2F603184&sref=https%3A%2F%2Fwww.townandcountrymag.com%2Fstyle%2Ffashion-trends%2Fg46934515%2Fbest-kentucky-oaks-pink-dresses%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link rapid-noclick-resp">Shop Now</a></p><p>Oh Oh Livia's Strapless Gingham Midi Dress</p><p>modaoperandi.com</p><p>$2795.00</p><span class="copyright">MODA OPERANDI</span>

Matchmaker Belted Floral-Print Linen and Silk-Blend Midi Dress

Florals are always a "do," and this '50s-inspired Zimmermann number is so pretty, you're sure to steal the attention from the fillies on race day.

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fwww.net-a-porter.com%2Fen-us%2Fshop%2Fproduct%2Fzimmermann%2Fclothing%2Fmidi-dresses%2Fmatchmaker-belted-floral-print-linen-and-silk-blend-midi-dress%2F1647597326830695&sref=https%3A%2F%2Fwww.townandcountrymag.com%2Fstyle%2Ffashion-trends%2Fg46934515%2Fbest-kentucky-oaks-pink-dresses%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link rapid-noclick-resp">Shop Now</a></p><p>Matchmaker Belted Floral-Print Linen and Silk-Blend Midi Dress</p><p>net-a-porter.com</p><p>$1950.00</p>

Bow-Detail Wool and Silk Midi Dress

This better-than-your-basic pink dress, featuring subtle shoulder bow, can go from office to Derby weekend without a second thought.

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fwww.mytheresa.com%2Fus%2Fen%2Fwomen%2Froland-mouret-bow-detail-wool-and-silk-midi-dress-pink-p00914309&sref=https%3A%2F%2Fwww.townandcountrymag.com%2Fstyle%2Ffashion-trends%2Fg46934515%2Fbest-kentucky-oaks-pink-dresses%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link rapid-noclick-resp">Shop Now</a></p><p>Bow-Detail Wool and Silk Midi Dress</p><p>mytheresa.com</p><p>$1150.00</p>

Floral Sleeveless Dress

This asymmetrical number has all the hallmarks of a memorable Oaks Day look: an elegant floral print, ruffled skirt, high-low silhouette, and a floral embellishment at the shoulder.

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fwww.saksfifthavenue.com%2Fproduct%2Fbadgley-mischka-floral-sleeveless-dress-0400020473791.html&sref=https%3A%2F%2Fwww.townandcountrymag.com%2Fstyle%2Ffashion-trends%2Fg46934515%2Fbest-kentucky-oaks-pink-dresses%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link rapid-noclick-resp">Shop Now</a></p><p>Floral Sleeveless Dress </p><p>saksfifthavenue.com</p><p>$487.50</p>

Giorgia Off-The-Shoulder Floral Ikat Midi Dress

Everything about this Markarian dress—from the sweet off-the-shoulder silhouette to the distinctive dropped waist and flouncy skirt to the soft floral design—screams Kentucky Oaks.

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fwww.modaoperandi.com%2Fwomen%2Fp%2Fmarkarian%2Fgiorgia-ikat-ots-dress%2F623872&sref=https%3A%2F%2Fwww.townandcountrymag.com%2Fstyle%2Ffashion-trends%2Fg46934515%2Fbest-kentucky-oaks-pink-dresses%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link rapid-noclick-resp">Shop Now</a></p><p>Giorgia Off-The-Shoulder Floral Ikat Midi Dress</p><p>modaoperandi.com</p><p>$1795.00</p><span class="copyright">Moda Operandi, Inc.</span>

Skielar Wrap-Effect Printed Plissé Silk-Georgette Dress

A long sleeve silk dress is the perfect style for the breezy outdoor event.

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fwww.net-a-porter.com%2Fen-us%2Fshop%2Fproduct%2Fralph-lauren-collection%2Fclothing%2Fmidi-dresses%2Fskielar-wrap-effect-printed-plisse-silk-georgette-dress%2F1647597325114800&sref=https%3A%2F%2Fwww.townandcountrymag.com%2Fstyle%2Ffashion-trends%2Fg46934515%2Fbest-kentucky-oaks-pink-dresses%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link rapid-noclick-resp">Shop Now</a></p><p>Skielar Wrap-Effect Printed Plissé Silk-Georgette Dress</p><p>net-a-porter.com</p><p>$3990.00</p>

Fleur Midi Dress in Blossom Hidden Dragon

When you want to stand out in a sea of pink dresses, look no further than Saloni's take which features a high collar and draped bodice with a vivid blooms.

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fsaloniworld.com%2Fen-us%2Fproducts%2Ffleur-ruffle-dress-in-rani-hidden-dragon&sref=https%3A%2F%2Fwww.townandcountrymag.com%2Fstyle%2Ffashion-trends%2Fg46934515%2Fbest-kentucky-oaks-pink-dresses%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link rapid-noclick-resp">Shop Now</a></p><p>Fleur Midi Dress in Blossom Hidden Dragon</p><p>saloniworld.com</p><p>$730.00</p>

Mattea Silk Dress

Not into florals? Polka dots are always a good idea.

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fwww.thereformation.com%2Fproducts%2Fmattea-silk-dress%2F1314888MVD.html%3Fdwvar_1314888MVD_color%3DMVD&sref=https%3A%2F%2Fwww.townandcountrymag.com%2Fstyle%2Ffashion-trends%2Fg46934515%2Fbest-kentucky-oaks-pink-dresses%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link rapid-noclick-resp">Shop Now</a></p><p>Mattea Silk Dress</p><p>thereformation.com</p><p>$298.00</p>

Pink Floral Print Tiered Midi Dress

Let your outfit do all the talking with a midi floral dress featuring a flattering sweetheart-neckline and twirl-ready tiered skirt.

<p><a href="https://us.self-portrait.com/products/pink-floral-print-tiered-midi-dress" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link rapid-noclick-resp">Shop Now</a></p><p>Pink Floral Print Tiered Midi Dress</p><p>self-portrait.com</p><p>$530.00</p>

Shop Now

Pink Floral Print Tiered Midi Dress

self-portrait.com

$530.00

You Might Also Like

Advertisement