Prepare to SERVE at Keeneland this fall with this perfect sleek dress featuring a boat neck silhouette and draping that flows all the way down.
Model in Dark Brown is 5'6" with a 32DD bust, 27" waist, 36" hips, and wearing a medium.
Model usually wears size 4.
This item runs true to size.
Model in Deep Blue is 5'8" with a 32D bust, 27" waist, 36" hips, and wearing a small.
Model usually wears size 4.
This item runs true to size.
Daily Double Dress
Regular price
$ 54.00
Save $ -54.00
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Everyone needs a LBD! Our Daily Double Dress is the cutest little strapless number with floral appliqué flowers and a front tie!
Model is 5'8" with a 32D bust, 27" waist, 36" hips, and wearing a small.
Model usually wears size 4.
This item runs true to size.
Stella Dress
Regular price
$ 64.00
Save $ -64.00
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This chocolate brown maxi dress is giving pure ELEGANCE! Our Stella Dress offers a high neckline with a fitted waist and side slit!
Model is 5'4" with a 32 bust, 25” waist, 35" hips, and wearing a small.
Model usually wears size 2.
This item runs true to size.
Lorelai Dress
Regular price
$ 62.00
Save $ -62.00
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This maxi has CHIC written all over it! The grey satin fabric and black lace strap detailing makes for the most stunning formal dress!
Model is 5'8" with a 32D bust, 27" waist, 36" hips, and wearing a small.
Model usually wears size 4.
This item runs true to size.
Amber Dress
Regular price
$ 72.00
Save $ -72.00
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This GORGEOUS soft ruffle skirt and flutter sleeve micro polka dot black dress would look so cute paired with black boots for a GNO!
Model is 5'8" with a 32D bust, 27" waist, 36" hips, and wearing a small.
Model usually wears size 4.
This item runs true to size.
Noah Dress
Regular price
$ 68.00
Save $ -68.00
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Here at Calypso we love a throwback. This backless turtleneck is sure to give you a timeless look perfect for any occasion.
Model is 5'4" with a 32 bust, 25" waist, 35" hips, and wearing a small.
Model usually wears a size 2.
This item runs true to size.
Top Tier Dress
Regular price
$ 68.00
Save $ -68.00
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Who doesn't love a RED maxi dress?! Get ready to turn head in the Top Tier Dress with white micro polka dots and a tie open back!
Model is 5'8" with a 32D bust, 27" waist, 36" hips, and wearing a small.
Model usually wears size 4.
This item runs true to size.
Kit Dress
Regular price
$ 62.00
Save $ -62.00
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A day-to-night dress? Yes, please! Skip the outfit change and keep going all night in this perfect chocolate brown floral off-the-shoulder dress.
Model is 5'4" with a 32 bust, 25" waist, 35" hips, and wearing a small.
Model usually wears a size 2
Item runs true to size.
Maria Dress
Regular price
$ 50.00
Save $ -50.00
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The most iconic strapless bodycon dress, or in other words the Maria Dress. With a beautiful ombre of dark colors this dress is perfect for date night or a girls night out!
Model is 5'6" with a 32DD bust, 27" waist, 36" hips, and wearing a medium.
Model usually wears size 4.
This item runs true to size.
Across The Board Dress
Regular price
$ 64.00
Save $ -64.00
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This black maxi is giving pure elegance! Our Across The Board Dress has stunning lace details with a bustier top!
Model is 5'8" with a 32D bust, 27" waist, 36" hips, and wearing a small.
Model usually wears size 4.
This item runs true to size.
Charleston Dress
Regular price
$ 56.00
Save $ -56.00
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This little brown dress is the perfect addition to your fall wardrobe! The white lace detail and micro polka dots make for an adorable touch!
Model is 5'8" with a 32D bust, 27" waist, 36" hips, and wearing a small.
Model usually wears size 4.
This item runs true to size.
Alumni Dress
Regular price
$ 78.00
Save $ -78.00
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Say hello to the athletic dress of your DREAM! Kentucky girls, this stretchy all black athletic dress with built in shorts and a bra is made for YOU!
Model 1 is 5'10" with a 36" bust, 31" waist, 41" hips, and wearing a medium.
Model 2 is 5'6" with a 32DD bust, 27" waist, 36" hips, and wearing a small.
Model 2 usually wears size 4.
This item runs true to size.
My Lover Dress
Regular price
$ 50.00
Save $ -50.00
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No one does sun dresses better than Calypso... and this yellow maxi is no exception. The dainty floral pattern throughout with a small bow detailing in the front would be perfect for Keeneland or vacation!
Model is 5'6" with a 32DD bust, 27" waist, 36" hips, and wearing a small.
Model usually wears size 4.
This item runs true to size.
Emmett Dress
Regular price
$ 72.00
Save $ -72.00
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Florals are for every season! This mini strapless dress with a blue floral pattern and a bow in the back to snatch the waist can't WAIT for Keeneland.
Model is 5'6" with a 32DD bust, 27" waist, 36" hips, and wearing a medium.
Model usually wears size 4.
This item runs true to size.
Starlet Dress
Regular price
$ 72.00
Save $ -72.00
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Bring the drama with this beautiful black gown. The starlet dress features a strapless, backless design and sweeping silhouette that is detailed with floral embroidery.
Model is 5'4" with a 32 bust, 25" waist, 35" hips, and wearing a small.
Model usually wears a size 2
This items runs true to size.
Churchill Dress
Regular price
$ 50.00
Sale price
$ 35.00
Save $ 15.00
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FINAL SALE
Who doesn't love florals for spring? This baby doll dress with an ivory base and blue roses is SCREAMING derby!
Model is 5'6" with a 32DD bust, 27" waist, 36" hips, and wearing a medium.
Model usually wears size 4.
This item runs true to size.
Snap The Ball Dress
Regular price
$ 48.00
Sale price
$ 36.00
Save $ 12.00
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A casual, but cute dress is exactly what we want for tailgating! This strapless mini dress with a bubble skirt and ruching along the bodice is flattering and perfect for Caturday.
Model is 5'8 with a 33" bust, 27" waist, 33" hips, and wearing a small.
Model typically wears a size 0/2.
This item runs true to size!
Winning Bet Dress
Regular price
$ 56.00
Save $ -56.00
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Beautiful white dress with baby blue prints throughout. She has bows to secure for the sleeves and has a buttery soft material.
Model is 5'8 with a 33" bust, 27" waist, 33" hips, and wearing a small.
Model typically wears a size 0/2.
This item runs true to size!
Aspen Dress
Regular price
$ 38.00
Save $ -38.00
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The Aspen dress is everything and more a girl could want for date night. This stretchy, bodycon dress features an open back for a sexy but elevated look. While still keeping it classy this mini dress has the perfect arrangment of dark browns, light browns and burnt sienna colors.
Model is 5'6" with a 32DD bust, 27" waist, 36" hips, and wearing a medium.
Model usually wears size 4.
This item runs true to size.
Full Moon Dress
Regular price
$ 46.00
Save $ -46.00
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THE dress for graduation is finally here! This form fitting, square neck mini is so flattering and perfect for any grad/bride!
Model is 5'8 with a 33" bust, 27" waist, 33" hips, and wearing a small.
Model typically wears a size 0/2.
This item runs true to size!
Shay Dress
Regular price
$ 52.00
Save $ -52.00
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The MOST flattering gameday dress! This buttery soft material with a mockneck is SO ready for Caturday!
Model is 5'9" with a 33" bust, 29" waist, 39" hips, and wearing a medium.
Shay is wearing Go For Gold Necklace
Item runs slightly fitted.
Grad Time Dress
Regular price
$ 52.00
Save $ -52.00
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Calling all grads OR brides.... this strapless white dress with a small bow detail in the front is so elegant with the sweetest fit.
Model is 5'8 with a 33" bust, 27" waist, 33" hips, and wearing a small.
Model typically wears a size 0/2.
This item runs true to size!
Dance With Me Dress
Regular price
$ 68.00
Save $ -68.00
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Denim dresses are IT this summer. Country concerts, horse races, or a little girls brunch would be perfect to take this one out. The button detailing along the front of the dress is SO cute.
Model is 5'3 with a 32B bust, 26" waist, 36" hips, and wearing a small.
Model typically wear a 0/2.
This item runs true to size.
Salem Dress
Regular price
$ 68.00
Save $ -68.00
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Casual sun dresses are ALWAYS a must for spring/summer! With the stretchy material along the bodice and a flowy skirt, she'd be the MOMENT with a little cardigan and sneakers.
Model is 5'8 with a 33" bust, 27" waist, 33" hips, and wearing a small.
Model typically wears a size 0/2.
This item runs true to size!
Iris Dress
Regular price
$ 62.00
Save $ -62.00
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The perfect mini dress for Keeneland has officially arrived!!
The Iris dress features a flowy skirt, spaghetti straps, a little ribbon tie detail at the neckline, and a blue floral pattern perfect for every occasion!
Model is 5'6" with a 32DD bust, 27" waist, 36" hips, and wearing a medium.
Model usually wears size 4.
This item runs true to size.
Literally Dress
Regular price
$ 54.00
Save $ -54.00
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Say hello to the most adorable blue gingham high neck, smocked, drop waist mini dress!
Pairs well with cowgirl boots and gold jewelry!
Model is 5'6" with a 32DD bust, 27" waist, 36" hips, and wearing a medium.
Model usually wears size 4.
This item runs true to size.
Never Let Go Dress
Regular price
$ 56.00
Save $ -56.00
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SHOW STOPPING!! This mini halter dress with a built in belt and a brown striped design is going to turn heads for fall meet!
Model is 5'6" with a 32DD bust, 27" waist, 36" hips, and wearing a medium.
Model usually wears size 4.
This item runs true to size.
Amour Dress
Regular price
$ 70.00
Save $ -70.00
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This pink floral dress is pure romance! With its soft hues, graceful flow, and beautiful neck line, it's perfect for a sunny day or a sweet soirée!
Model is 5'8 with a 33" bust, 27" waist, 33" hips, and wearing a small.
Model typically wears a size 0/2.
This item runs true to size!
True Blue Dress
Regular price
$ 54.00
Save $ -54.00
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Royal blue perfection with a sweetheart neckline and the cutest tie-back moment (trust us, the back is EVERYTHING).
Model is 5'6" with a 32DD bust, 27" waist, 36" hips, and wearing a medium.
Model usually wears size 4.
This item runs true to size.
Beat 'Em Dress
Regular price
$ 58.00
Save $ -58.00
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Get gameday ready with this mini blue plaid dress with lace outlining on the neckline and an adjustable bow!
Model is 5'6" with a 32DD bust, 27" waist, 36" hips, and wearing a medium.
Model usually wears size 6.
This item runs true to size.
Sweet Emotion Dress
Regular price
$ 48.00
Save $ -48.00
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A FALL STAPLE for you! This beautiful knit black dress with a white curled hemline and sleeve would be the perfect look for Thanksgiving!
Model 1 is 5'4" with a 32 bust, 25” waist, 35" hips, and wearing a XS.
Model usually wears size 2.
This item runs true to size.
Model 2 is 5'6" with a 34DD bust, 26” waist, 37” hips, and wearing a SMALL.
Model is usually a size 6.
Special Teams Dress
Regular price
$ 52.00
Save $ -52.00
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The perfect piece for gameday is ALWAYS going to be a dress! This checkered blue and white strapless mini dress with a dainty bow is ready for Caturday!
Model is 5'8 with a 33" bust, 27" waist, 33" hips, and wearing a small.
Model typically wears a size 0/2.
This item runs true to size!
Degree Hotter Dress
Regular price
$ 42.00
Save $ -42.00
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All 2025 grads, we got you with this GORG white mini dress with a small slit, plus the sweetest neckline! Pair with either white OR blue heels for the UK girls!
Model is 5'8 with a 33" bust, 27" waist, 33" hips, and wearing a small.
Model typically wears a size 0/2.
This item runs true to size!
Wildcat Dress
Regular price
$ 38.00
Save $ -38.00
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We LOVE gameday at Calypso and this denim long sleeve dress is calling your name. Silver buttons down the front with a collared neckline.
Pair her with cowboy boots to SLAY football season.
Model in blue is 5'8 with a 33" bust, 27" waist, 33" hips, and wearing a small.
Model in blue typically wears a size 0/2.
Model in denim is 5'9 with a 35" bust, 28" waist, 38" hips, and wearing a small.
Model in denim typically wears a size 6.
This item runs true to size!
Full Glam Dress
Regular price
$ 60.00
Save $ -60.00
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Sexy meets CHIC! This mini dress features a flattering deep V-neckline with faux front pockets, adding a touch of sophistication and allure!
Model is 5'6" with a 32DD bust, 27" waist, 36" hips, and wearing a small.
Model usually wears size 4.
This item runs true to size.
Cherish You Dress
Regular price
$ 42.00
Save $ -42.00
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This dress is effortlessly chic! With its sleek, one-shoulder design and form-fitting silhouette, it’s the perfect mix of elegance and allure.
Comes in red, light pink, AND white!
Model is 5'6" with a 32DD bust, 27" waist, 36" hips, and wearing a medium.
Model usually wears size 4.
This item runs long.
Kiss Me At Midnight Dress
Regular price
$ 44.00
Sale price
$ 30.00
Save $ 14.00
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FINAL SALE
HEADS. WILL. TURN. to see you in our new Kiss Me At Midnight Dress! The perfect touch of subtle sparkle overtop a GORG cheetah maxi! Perfect way to step out for date night, formal, or anytime you're in the mood to slay!
Sparkled cheetah maxi dress with black crossover straps.
Model 1 is 5'4 with a 32C, 28" waist, 38" hips, and is wearing a small.
Model 2 is 5'6" with a 32DD bust, 27" waist, 36" hips, and wearing a medium.
Model 2 usually wears size 4.
This item runs true to size.
One More Time Dress
Regular price
$ 68.00
Sale price
$ 35.00
Save $ 33.00
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FINAL SALE
Yellow dresses ALWAYS scream summer! This tiered, eyelet dress with bow detailings on the front and back is ready for any event!
Model is 5'8 with a 33" bust, 27" waist, 33" hips, and wearing an XS.
Model typically wears a size 0/2.
This item runs true to size!
Proud Park Dress
Regular price
$ 52.00
Sale price
$ 20.00
Save $ 32.00
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FINAL SALE
Such a versatile and fun dress with the flattering fit and adorable puff sleeves!
Model is 5'9 with a 35" bust, 28" waist, 38" hips, and wearing a small.
Model typically wears a size 6.
This item runs true to size.
Bittersweet Dress
Regular price
$ 52.00
Save $ -52.00
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Have a date night coming up but have nothing to wear? We got you!! This mauve strapless dress with a minimalistic floral pattern is perfect for any special occasion.
Model is 5'6" with a 32DD bust, 27" waist, 36" hips, and wearing a medium.
Model usually wears size 4.
This item runs true to size.
Sunday Mood Dress
Regular price
$ 58.00
Save $ -58.00
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The floral dress of our DREAMS! She's a maxi with short sleeves and a built in bra with lace detailing, not to mention the sweetest floral pattern.
Model is 5'8 with a 33" bust, 27" waist, 33" hips, and wearing a small.
Model typically wears a size 0/2.
This item runs true to size!
Wyoming Dress
Regular price
$ 72.00
Save $ -72.00
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The Wyoming Dress takes florals into fall. With its strapless maxi silhouette, earthy brown-and-blue print, and flattering smocked bodice, it’s an effortless piece you’ll wear on repeat.
Layer it with a denim jacket or chunky knit for that perfect crisp weather vibe.
Model is 5'4" with a 32 bust, 25" waist, 35" hips, and wearing a small.
Model usually wears size 2.
Item runs true to size.
Gather Around Dress
Regular price
$ 56.00
Save $ -56.00
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Talk about dreamy, this mini slip dress with a purple floral print and lace detailing is ready for going out or date night!
Model is 5'6" with a 32DD bust, 27" waist, 36" hips, and wearing a medium.
Model usually wears size 4.
This item runs true to size.
Styles Dress
Regular price
$ 54.00
Save $ -54.00
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Meet your new obsession the Styles Dress is a burgundy halter mini dress featuring the cutest lace detail, and fits like a glove!!
Model is 5'6" with a 32DD bust, 27" waist, 36" hips, and wearing a medium.
Model usually wears size 4.
Item runs slightly big.
Windsor Dress
Regular price
$ 50.00
Sale price
$ 30.00
Save $ 20.00
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FINAL SALE
Talk about elegant, this ivory dress with a royal blue floral pattern has the perfect bodice cut with a flowy skirt. Giving us all the Europe summer vibes!
Model is 5'6" with a 32DD bust, 27" waist, 36" hips, and wearing a medium.
Model usually wears size 4.
This item runs true to size.
Cameron Dress
Regular price
$ 68.00
Save $ -68.00
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It's giving 2000s BADDIE! This eyelet trimmed paid dress is READY for a night on the town with some tall black boots.
Model is 5'6" with a 32DD bust, 27" waist, 36" hips, and wearing a medium.
Model usually wears size 4.
This item runs true to size.
Better Half Dress
Regular price
$ 58.00
Save $ -58.00
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Floral dresses are always an IN for us! Not to mention the navy detailing and rouching makes her the sweetest addition to our dress collection.
Model is 5'8 with a 33" bust, 27" waist, 33" hips, and wearing a small.