Say hello to the CUTEST halter neck dress with textured black polka dots scattered throughout!
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.
Leave It With Me Dress
Regular price
$ 64.00
Save $ -64.00
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At Calypso polka dots are a fall ESSENTIAL! The Leave It With Me Dress is the perfect piece to add a neutral maxi dress in your fall wardrobe!
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.
Shay Dress
Regular price
$ 52.00
Sale price
$ 40.00
Save $ 12.00
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FINAL SALE
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.
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.
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.
Bradford Dress
Regular price
$ 62.00
Save $ -62.00
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Heading to a concert downtown? This mini denim dress is all you need for the perfect night!
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.
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.
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.
Winning Bet Dress
Regular price
$ 56.00
Sale price
$ 40.00
Save $ 16.00
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FINAL SALE
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!
Wildcat Dress
Regular price
$ 38.00
Sale price
$ 30.00
Save $ 8.00
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FINAL SALE
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!
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.
My Lover Dress
Regular price
$ 50.00
Sale price
$ 40.00
Save $ 10.00
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FINAL SALE
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.
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.
Grad Time Dress
Regular price
$ 52.00
Sale price
$ 40.00
Save $ 12.00
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FINAL SALE
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!
No Other Feeling Dress
Regular price
$ 64.00
Save $ -64.00
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Who is looking for the most FLATTERING mini dress with BUILT IN SHORTS?! This sexy, yet chic mini dress with fake pockets is to DIE for!
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.
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.
Harvest Dress
Regular price
$ 62.00
Save $ -62.00
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Give main character energy in the Harvest Dress.
A rich brown dress with a drop waist that flows into a sheer mesh skirt.
High side slit for major leg moment.
Earthy, effortless, and everything.
Model is 5'6" with a 32DD bust, 27" waist, 36" hips, and wearing a medium.
Model usually wears size 6.
Existing Dress
Regular price
$ 60.00
Save $ -60.00
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She's giving certified COOL GIRL! This thin, breathable, double lined, black polka dot dress is our new FAV for fall! Turn heads at Keeneland in this new midi!
Comes with matching neck scarf!
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.
Avery Dress
Regular price
$ 62.00
Save $ -62.00
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At Calypso polkadots are here to stay! The Avery Dress is the perfect piece to add a pop of color in your fall wardrobe.
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.
Always Remember Dress
Regular price
$ 56.00
Save $ -56.00
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It’s definitely time for a girls' night, and the Always Remember Dress is the ultimate fall pick! Embrace the rich chocolate brown mesh and sleek v-neck design to create a look that’s perfectly polished and unforgettable.
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.
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.
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.
Wide Awake Dress
Regular price
$ 66.00
Save $ -66.00
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Prepare to feel SNATCHED in this perfect polka dot midi dress!! You will want to wear this dress everywhere you go!!
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.
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.
Full Moon Dress
Regular price
$ 46.00
Sale price
$ 40.00
Save $ 6.00
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FINAL SALE
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!
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!
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.
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.
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.
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!
Dance With Me Dress
Regular price
$ 68.00
Sale price
$ 40.00
Save $ 28.00
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FINAL SALE
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.
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!
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.
Big Winner Dress
Regular price
$ 76.00
Save $ -76.00
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Ready to turn heads? The Big Winner Dress nails effortless elegance with its off-the-shoulder neckline and flowy pleated skirt.
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.
More Than Friends Dress
Regular price
$ 46.00
Save $ -46.00
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Nothing is more on trend than polkadots! Keep your closet filled with the latest by adding the More than friends dress to your collection.
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.
Devon Dress
Regular price
$ 62.00
Save $ -62.00
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Elevate your wardrobe with the Devon Dress, patterned with mini polkadots that make a subtle yet striking statement.
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.
Pretty and Witty Dress
Regular price
$ 74.00
Save $ -74.00
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Who is looking for the most FLATTERING mini dress? This chic and floral mini dress with faux pockets is to DIE for!
Model is 5'8" with a 32D bust, 27" waist, 36" hips, and wearing asmall.
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.
Margo Dress
Regular price
$ 72.00
Save $ -72.00
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Prepare to SERVE this fall with this perfect sleek dress featuring a brown polka dot maxi 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.
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.
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.
Better Half Dress
Regular price
$ 48.00
Save $ -48.00
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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!
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.
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!
Lainey Dress
Regular price
$ 56.00
Save $ -56.00
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The Lainey Dress is a plum purple halter mini Perfect for making a statement at any event, its sleek fit will keep your style on point.
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.
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!
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!
Grad Season Dress
Regular price
$ 56.00
Sale price
$ 20.00
Save $ 36.00
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FINAL SALE
Calling all grads... this dress is FOR YOU! This body con white mini dress will make your special day even better, the sheer rouching adds the perfect amount of detail!
Wear the straps on OR off the shoulder!
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!
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.
Model typically wears a 4.
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.