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Calypso Boutique Calypso Boutique
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  • COLLECTIONS
    • FALL 2025
    • HOLIDAY LOOKS
    • FAN CLUB
    • LAYLA + SHAY POPE X CATURDAY
    • KATIE FAWN X CALYPSO
  • New
    New Gameday
    All Kentucky
    SEC
    Collegiate Colors
    Gameday Accessories
    New Tops
    Going Out Tops
    Sweaters
    Leather Top
    Corset Top
    New Bottoms
    Jeans
    Shorts
    Skirts
    Pants
    New Dresses
    Keeneland
    Going Out
    Midis
    Maxis
    LBD
    LWD
    New Jewelry
    Bracelets
    Earrings
    Necklaces
    Rings
    New Outerwear
    Leather Jackets
    Puffers
    Moto Jackets
    Blazers
    New Calypso Customs
    Custom Loungewear
    Custom Tees
    Custom Accessories
    Custom Hats
    Gift Shop
    Gift Items
    Gift Card
    New Best Sellers
    New Restocks
  • Gameday
    • All Gameday
    • Gameday Hats
    • Gameday Tops + Jackets
    • Gameday Bottoms
    • Gameday Dresses
    • Gameday Jewelry
    • Gameday Bags
    • Gameday Accessories
    • Gameday Bundles
  • Clothing
    Tops
    Going Out Tops
    Leather Tops
    Corset Tops
    Sweaters
    Tiny Tanks
    Bottoms
    Jeans
    Shorts
    Skirts
    Pants
    Leather Pants
    Leather Skirts
    Dresses
    KEENELAND
    Midis
    Maxis
    Going Out Dresses
    LBD
    LWD
    Graduation Dresses
    Sets & Rompers
    All Sets
    All Rompers
    Playsuits
    Custom Apparel
    CAPSULE WARDROBE COLLECTION
    Custom Tees
    Custom Sweatshirts
    Custom Jewelry
    Custom Accessories
    Outerwear
    Leather Jackets
    Puffers
    Vests
    Bombers
    Blazers
    Moto Jackets
    Basics
    Tees/Tanks
    Loungewear
    Parachute Pants
    Workwear
    Blazers
    Trousers
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    Gift Items
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  • KY COLLECTION
    • KY
    • LEX
  • VINTAGE
  • Accessories
    Jewelry
    Water Resistant Jewelry
    Calypso Custom Jewelry
    Necklaces
    Earrings
    Bracelets
    Hand Chains
    Rings
    Purses
    Hats
    Sunglasses
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  • Shoes
    • Sandals & Platforms
    • Boots
    • Heels
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  • FAN FAVS
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    • Gameday Jewelry
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  • Sale
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  • HOLIDAY LOOKS
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Orders placed Nov 19th - Dec 25th can be returned until Jan 17th for exchange OR in store credit! For refunds, we will offer 14 days from the date of purchase per regular policy.
☆ GAMEDAY SALE ☆ 25% OFF SELECT STYLES
Questions? Call (859) 225-3810
Quick view
Leave It With Me Dress
$ 64.00
Sold Out
Trackside Dress
$ 62.00
Quick view
Big Winner Dress
$ 76.00
Quick view
Top Tier Dress
$ 68.00
Quick view
Across The Board Dress
$ 64.00
Quick view
Velma Dress
$ 60.00
Quick view
Lorelai Dress
$ 62.00
Quick view
Noah Dress
$ 68.00
Sold Out
Lady Luck Dress
$ 64.00
Sold Out
Starlet Dress
$ 72.00
Quick view
Heart of Mine Dress
$ 62.00
Sold Out
Stella Dress
$ 64.00
Sold Out
Erin Skirt
$ 50.00
Quick view
Harvest Dress
$ 62.00
Quick view
Maria Dress
$ 50.00
Sold Out
Santana Dress
$ 78.00
Quick view
Next Mistake Skirt
$ 48.00
Sale
Quick view
Almost Famous Skirt
Regular price $ 38.00 Sale price$ 30.00 Save $ 8.00
Quick view
My Lover Dress
$ 50.00
Sale
Quick view
Down The Track Dress
Regular price $ 38.00 Sale price$ 30.00 Save $ 8.00
Sale
Quick view
St Bart's Dress
Regular price $ 54.00 Sale price$ 30.00 Save $ 24.00
Leave It With Me Dress
Leave It With Me Dress
Leave It With Me Dress
Leave It With Me Dress
Leave It With Me Dress
Leave It With Me Dress
Leave It With Me Dress
Leave It With Me Dress
Leave It With Me Dress
Leave It With Me Dress
Leave It With Me Dress
Leave It With Me Dress

Leave It With Me Dress

Regular price $ 64.00 Save $ -64.00
/

  • 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.
Big Winner Dress
Big Winner Dress
Big Winner Dress
Big Winner Dress
Big Winner Dress
Big Winner Dress
Big Winner Dress
Big Winner Dress
Big Winner Dress
Big Winner Dress
Big Winner Dress
Big Winner Dress
Big Winner Dress
Big Winner Dress
Big Winner Dress
Big Winner Dress
Big Winner Dress
Big Winner Dress
Big Winner Dress
Big Winner Dress
Big Winner Dress
Big Winner Dress
Big Winner Dress
Big Winner Dress
Big Winner Dress
Big Winner Dress
Big Winner Dress
Big Winner Dress

Big Winner Dress

Regular price $ 76.00 Save $ -76.00
/

  • 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. 
Top Tier Dress
Top Tier Dress
Top Tier Dress
Top Tier Dress
Top Tier Dress
Top Tier Dress
Top Tier Dress
Top Tier Dress
Top Tier Dress
Top Tier Dress
Top Tier Dress
Top Tier Dress
Top Tier Dress
Top Tier Dress
Top Tier Dress
Top Tier Dress

Top Tier Dress

Regular price $ 68.00 Save $ -68.00
/

  • 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.
Across The Board Dress
Across The Board Dress
Across The Board Dress
Across The Board Dress
Across The Board Dress
Across The Board Dress
Across The Board Dress
Across The Board Dress
Across The Board Dress
Across The Board Dress

Across The Board Dress

Regular price $ 64.00 Save $ -64.00
/

  • 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.
Velma Dress
Velma Dress
Velma Dress
Velma Dress
Velma Dress
Velma Dress
Velma Dress
Velma Dress

Velma Dress

Regular price $ 60.00 Save $ -60.00
/

  • 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.
Lorelai Dress
Lorelai Dress
Lorelai Dress
Lorelai Dress
Lorelai Dress
Lorelai Dress
Lorelai Dress
Lorelai Dress
Lorelai Dress
Lorelai Dress
Lorelai Dress
Lorelai Dress

Lorelai Dress

Regular price $ 62.00 Save $ -62.00
/

  • 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.
Noah Dress
Noah Dress
Noah Dress
Noah Dress
Noah Dress
Noah Dress
Noah Dress
Noah Dress
Noah Dress
Noah Dress
Noah Dress
Noah Dress
Noah Dress
Noah Dress
Noah Dress
Noah Dress
Noah Dress
Noah Dress
Noah Dress
Noah Dress
Noah Dress
Noah Dress
Noah Dress
Noah Dress
Noah Dress
Noah Dress
Noah Dress
Noah Dress
Noah Dress
Noah Dress
Noah Dress
Noah Dress
Noah Dress
Noah Dress

Noah Dress

Regular price $ 68.00 Save $ -68.00
/

  • 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. 
Heart of Mine Dress
Heart of Mine Dress
Heart of Mine Dress
Heart of Mine Dress
Heart of Mine Dress
Heart of Mine Dress
Heart of Mine Dress
Heart of Mine Dress
Heart of Mine Dress
Heart of Mine Dress
Heart of Mine Dress
Heart of Mine Dress
Heart of Mine Dress
Heart of Mine Dress
Heart of Mine Dress
Heart of Mine Dress
Heart of Mine Dress
Heart of Mine Dress
Heart of Mine Dress
Heart of Mine Dress
Heart of Mine Dress
Heart of Mine Dress

Heart of Mine Dress

Regular price $ 62.00 Save $ -62.00
/

  • 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. 

 

Harvest Dress
Harvest Dress
Harvest Dress
Harvest Dress
Harvest Dress
Harvest Dress
Harvest Dress
Harvest Dress
Harvest Dress
Harvest Dress
Harvest Dress
Harvest Dress
Harvest Dress
Harvest Dress

Harvest Dress

Regular price $ 62.00 Save $ -62.00
/

  • 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.

 

Maria Dress
Maria Dress
Maria Dress
Maria Dress
Maria Dress
Maria Dress
Maria Dress
Maria Dress
Maria Dress
Maria Dress
Maria Dress
Maria Dress

Maria Dress

Regular price $ 50.00 Save $ -50.00
/

  • 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.
Next Mistake Skirt
Next Mistake Skirt
Next Mistake Skirt
Next Mistake Skirt
Next Mistake Skirt
Next Mistake Skirt
Next Mistake Skirt
Next Mistake Skirt
Next Mistake Skirt
Next Mistake Skirt
Next Mistake Skirt
Next Mistake Skirt
Next Mistake Skirt
Next Mistake Skirt
Next Mistake Skirt
Next Mistake Skirt
Next Mistake Skirt
Next Mistake Skirt
Next Mistake Skirt
Next Mistake Skirt
Next Mistake Skirt
Next Mistake Skirt
Next Mistake Skirt
Next Mistake Skirt
Next Mistake Skirt
Next Mistake Skirt

Next Mistake Skirt

Regular price $ 48.00 Save $ -48.00
/

  • The skirt of our DREAMS! This fully lace maxi skirt would be SO cute for any concert you're going to this summer. 
  • This skirt is sheer and doesn't have underlining. 
  • 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.

Almost Famous Skirt
Almost Famous Skirt
Almost Famous Skirt
Almost Famous Skirt
Almost Famous Skirt
Almost Famous Skirt
Almost Famous Skirt
Almost Famous Skirt
Almost Famous Skirt
Almost Famous Skirt

Almost Famous Skirt

Regular price $ 38.00 Sale price $ 30.00 Save $ 8.00
/

FINAL SALE

  • A black maxi skirt is a closet ESSENTIAL... she has a buttery soft material and is perfect to pair with the matching top or a graphic tee.
  • Top and skirt sold separately. 
  • 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
My Lover Dress
My Lover Dress
My Lover Dress
My Lover Dress
My Lover Dress
My Lover Dress
My Lover Dress
My Lover Dress
My Lover Dress
My Lover Dress
My Lover Dress
My Lover Dress
My Lover Dress
My Lover Dress
My Lover Dress
My Lover Dress
My Lover Dress

My Lover Dress

Regular price $ 50.00 Save $ -50.00
/

  • 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.
Down The Track Dress
Down The Track Dress
Down The Track Dress
Down The Track Dress
Down The Track Dress
Down The Track Dress
Down The Track Dress
Down The Track Dress
Down The Track Dress
Down The Track Dress
Down The Track Dress
Down The Track Dress
Down The Track Dress
Down The Track Dress
Down The Track Dress
Down The Track Dress

Down The Track Dress

Regular price $ 38.00 Sale price $ 30.00 Save $ 8.00
/

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 runs true to size!
St Bart's Dress
St Bart's Dress
St Bart's Dress
St Bart's Dress
St Bart's Dress
St Bart's Dress
St Bart's Dress
St Bart's Dress
St Bart's Dress
St Bart's Dress
St Bart's Dress
St Bart's Dress
St Bart's Dress
St Bart's Dress
St Bart's Dress
St Bart's Dress
St Bart's Dress
St Bart's Dress
St Bart's Dress
St Bart's Dress
St Bart's Dress
St Bart's Dress
St Bart's Dress
St Bart's Dress
St Bart's Dress
St Bart's Dress

St Bart's Dress

Regular price $ 54.00 Sale price $ 30.00 Save $ 24.00
/

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!

QUESTIONS or ORDER ISSUES?

TEXT US AT 859-225-3810! Emails can go to spam, so texting is the best most urgent way to contact us! If email communication is preferred, please reply to your confirmation email to ensure we receive! ♡

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