Give us ALL the maxi dresses!! This linen white dress with a beautiful royal blue floral pattern can't wait to go to Keeneland with you! Straps also cross in the back for an added detail.
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!
Asher Top
Regular price
$ 34.00
Save $ -34.00
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Game day season is year round at Calypso! This royal blue tee with ruffle sleeves can be dressed up or down with jeans or workwear!
Model is 5'6" with a 32DD bust, 27" waist, 36" hips, and wearing a medium.
Model usually wears a size 4.
This item runs true to size.
No Drama Top
Regular price
$ 38.00
Save $ -38.00
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The perfect going out top is finally here! This square neck, classic black tank with ruching on the sides is SO flattering and can go with any bottoms in any season.
Model is 5'6" with a 32DD bust, 27" waist, 36" hips, and wearing a medium.
Model usually wears a size 4.
This item runs slightly big.
Buzzer Beater Sweater
Regular price
$ 46.00
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This striped sweater is the perfect basic! Thick knitted material and fits slightly oversized!
Comes in royal blue AND deep red!
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.
Hilton Head Top
Regular price
$ 38.00
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The PERFECT basic, this halter top with a deep V-neck and an open back is ready for a night out!
Pair with a skirt and boots for the cutest GNO fit!
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.
Life Goes On Dress
Regular price
$ 42.00
Save $ -42.00
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Flowy dresses all spring long PLEASE! This strapless maxi with a knot design in the front and an open back is BEGGING to go to the derby with you this year.
Model is 5'6" with a 32DD bust, 27" waist, 36" hips, and wearing a medium.
Model usually wears a size 4.
This item runs true to size.
Get With It Top
Regular price
$ 42.00
Save $ -42.00
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Who doesn't love an open knit sweater? This oversized top with a cable knit design throughout is the perfect swim suit cover up or top for your brunch on the beach!
Model is 5'6" with a 32DD bust, 27" waist, 36" hips, and wearing a medium.
Model usually wears a size 4.
This item runs true to size.
West Skirt
Regular price
$ 32.00
Save $ -32.00
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Dark denim will always be a must have in your wardrobe. Our NEW mini skirt with a front cargo pocket & belt loops on the waistline make it more unique for your upcoming 'fits!
Model is 5'9 with a 35" bust, 28" waist, 38" hips, and wearing a medium.
Model typically wears a size 6.
This item runs true to size.
Perfect Day Dress
Regular price
$ 72.00
Save $ -72.00
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For all our girly girls..... this floral dress is for YOU! She has a beautiful floral pattern with a corset bodice and a flowy skirt, PLUS the bow detailing on the straps is giving all the fairy princess vibes we NEED this spring.
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!
To Be Loved Dress
Regular price
$ 56.00
Save $ -56.00
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It's officially Keeneland season again and what screams spring season more than an ADORABLE baby pink dress? She's strapless with a form fitting silhouette and flowy skirt, giving us the feminine feel we all LOVE.
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!
Ramsey Dress
Regular price
$ 66.00
Save $ -66.00
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This dress is a dreamy halter-neck maxi featuring a soft pastel floral print in shades of yellow and blush. With its flowy silhouette and subtle cutout detail under the bust, it’s the perfect blend of sweet and flirty!
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!
Me Before You Dress
Regular price
$ 88.00
Save $ -88.00
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This dress is a dreamy, tiered midi covered in delicate lavender rose prints with soft green leaves. Its flowy silhouette and layered ruffles give it a romantic, effortless charm—perfect for daytime outings, brunch dates, or a sweet spring moment.
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!
Nothing On You Dress
Regular price
$ 58.00
Save $ -58.00
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This dress is a bold yet timeless beauty in vibrant cobalt blue, featuring puff sleeves, a square neckline, and a flattering ruched bodice. With its effortless flow and open back, it’s perfect for making a statement while keeping it sweet and classic.
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!
New Me Top
Regular price
$ 38.00
Save $ -38.00
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Everyone knows this.... but no one does basics like Calypso! This grey baby tee is our take on the viral top everyones been loving! Buttons down the front make her so versatile, wear her with all the buttons up or take some 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 true to size!
Born Like You Top
Regular price
$ 42.00
Save $ -42.00
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Who said you couldn't be comfy in your going out 'fit? This buttery soft top has the most flattering neckline & a twist knot in the center! Pair with denim or a fun statement bottom for your next dinner date!
Comes in black and white.
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!
Take Me Home Dress
Regular price
$ 74.00
Save $ -74.00
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Soft AND romantic, this maxi with delicate lace details and a flowy tiered design is perfect for a beach vacation or a date night!
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!
Summer Lovin Dress
Regular price
$ 46.00
Save $ -46.00
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The PERFECT Keeneland dress is here! This strapless, ivory midi with a tight bodice and flowy skirt would be SHOW STOPPING for this season!
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.
Cloud Nine Romper
Regular price
$ 68.00
Save $ -68.00
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It's giving elegant, classy, and everything in between. This romper looks like a set, but she's all one piece! The gold buttons with the sleek white material is giving all the Sophia Richi vibes and we're OBSESSED.
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!
Easy On Me Dress
Regular price
$ 74.00
Save $ -74.00
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We love a dress with a feminine touch, this baby doll piece with lace detailing throughout and bows on the straps is guaranteed to turn heads anywhere you wear her.
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!
Carmen Top
Regular price
$ 38.00
Save $ -38.00
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A top that's SCREAMING summer country concert? YES PLEASE! This baby doll top with lace trimming and button detailing down the front can't wait to be paired with some boots and jean shorts this summer!
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!
Small Worlds Top
Regular price
$ 46.00
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Crochet is ALWAYS a yes for us! This open-knit vest with flower detailing throughout would be PERFECT for Railbird this summer!
Model is 5'8 with a 33" bust, 27" waist, 33" hips, and wearing a S/M.
Model typically wears a size 0/2.
This item runs true to size!
Like The Movies Dress
Regular price
$ 58.00
Save $ -58.00
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A slip dress is the IT girl dress for all grads or brides! She's simple, but SO elegant with the off white coloring and small bow detailing on the front.
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!
Walk On By Dress
Regular price
$ 68.00
Save $ -68.00
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Linen dresses are SCREAMING summer and this sky blue is the perfect match. The high neck cut and small slit detailing is perfect for any date night.
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!
Dream Girl Dress
Regular price
$ 58.00
Save $ -58.00
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Yellow is always the color of the summer! This sun dress with lace detailing throughout and a drop waist is SO ready for concerts!
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!
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!
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!
Becca Dress
Regular price
$ 64.00
Save $ -64.00
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Maxi dresses are for EVERY season! This multi-colored dark pink/orange dress with ruffles along the neckline and cutouts along the waist is so beautiful for fall!
Model is 5'6" with a 32DD bust, 27" waist, 36" hips, and wearing a medium.
