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.
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.
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 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.
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.
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.
Heart of Mine Dress
Regular price
$ 62.00
Save $ -62.00
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The Heart of Mine Dress is that girl. Made with stretchy mesh, long sleeves, and a high slit that does the most!
Model is 5'6" with a 32DD bust, 27" waist, 36" hips, and wearing a small.
Model usually wears a size 6.
This item runs slightly big.
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.
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.
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.
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.
Posey Dress
Regular price
$ 60.00
Save $ -60.00
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This maxi black and white polka dot dress is adorned with red flowers, a deep v-neck and an added neck scarf for that PERFECT chic look. The Posey Dress is chic, classic and fun!
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.
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.
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.
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.
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.
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.
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.
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.
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.
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!
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!
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!
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!
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.
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.
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!
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!
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!
Revolving Door Dress
Regular price
$ 58.00
Sale price
$ 30.00
Save $ 28.00
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FINAL SALE
This darling lavender slip dress is the perfect piece for a sexy night out or a relaxing night in! The lace trim and hugging fit is sure to boost your confidence!
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!
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.
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!
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.
On The Way Dress
Regular price
$ 36.00
Sale price
$ 30.00
Save $ 6.00
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FINAL SALE
OBSESSING over this new lace mini dress! This navy strapless dress has a double lined silhouette with sheer lace sleeves.
Pair her with tall boots or heels for the cutest look!
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!
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.
Grand Stand Dress
Regular price
$ 38.00
Sale price
$ 30.00
Save $ 8.00
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FINAL SALE
The classiest and sexiest fall dress has arrived! Full zip along the front and cargo pockets for detailing with the perfect charcoal color.
Model is 5'6" with a 32DD bust, 27" waist, 36" hips, and wearing a small.
Model usually wears size 2/4.
This item runstrue to size!
Down The Track Dress
Regular price
$ 38.00
Sale price
$ 30.00
Save $ 8.00
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FINAL SALE
Gorgeous grey maxi dress with rose detailing throughout. Ruching down the back and side seams to snatch your waist!
Model is 5'6" with a 32DD bust, 27" waist, 36" hips, and wearing a medium.
Model usually wears size 2/4.
This item runstrue to size!
Sadie Top
Regular price
$ 48.00
Sale price
$ 30.00
Save $ 18.00
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FINAL SALE
The IT girl going out top for fall! This longer corset with a tie in the back to secure is ready to be paired with a leather jacket and a skirt for a night out!
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 oversized.
Back Pass Jersey
Regular price
$ 48.00
Save $ -48.00
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Jerseys are the IT girl gameday piece and this blue one from one of our fav brands is ready for Caturday!
Kentucky and the number 65 embroidered on front and back.
Model is 5'6" with a 32DD bust, 27" waist, 36" hips, and wearing a Large.
Model usually wears size 2/4.
This item runs small!
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.
Take It Personal Dress
Regular price
$ 48.00
Save $ -48.00
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The IT dress this spring!!! This delicate pastel yellow maxi exudes charm and is perfect for the transition into warm weather.
Detailed with precious floral patterns as well as pink lace.
Model is 5'5" with a 34 bust, 26" waist, 32" hips, and wearing a small.
Model typically wears a 4.
This item runs true to size.
St Bart's Dress
Regular price
$ 54.00
Sale price
$ 30.00
Save $ 24.00
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FINAL SALE, NO RETURNS
She is giving classy & colorful in this beautiful midi dress!
The lace overlay on the bust, string-tie center, and lace-up back are all the details that make this a dress you can NOT pass up on getting.
This dress would look AMAZING at Derby, a summer wedding, or on a tropical vacation! Comes in two color-ways: avocado and dark mint.
Model in avocado is 5'9 with a 35" bust, 28" waist, 38" hips, and wearing a small.
Model typically wears a size 6.
Model in dark mint is 5'5" with a 34 bust, 26" waist, 32" hips, and wearing a small.