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.
Lorelai Dress
Regular price
$ 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
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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
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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
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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.
Lady Luck Dress
Regular price
$ 64.00
Save $ -64.00
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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.
Across The Board Dress
Regular price
$ 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.
Snap The Ball Dress
Regular price
$ 48.00
Save $ -48.00
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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!
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.
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.
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.
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.
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.
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.
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.
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.
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.
Model typically wears a size 0/2.
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!
Nina Dress
Regular price
$ 48.00
Save $ -48.00
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The Nina Dress is lowkey iconic. This navy blue midi brings the vibe with delicate lace trim on the collar and sleeves is perfect for chill brunches, museum dates, or just romanticizing your errands.
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.
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.
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.