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Calypso Boutique Calypso Boutique
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  • FALL 2025
  • COLLECTIONS
    • FALL COLLECTION
    • FAN CLUB
    • LAYLA + SHAY POPE X CATURDAY
    • KATIE FAWN X CALYPSO
  • New
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    All Rompers
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    Jewelry
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    Calypso Custom Jewelry
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    Purses
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  • Shoes
    • Sandals & Platforms
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☆ GAMEDAY SALE ☆ 25% OFF SELECT STYLES
Questions? Call (859) 225-3810
Orders with shoes: $7.95 SHIPPING CHARGE
Quick view
Leave It With Me Dress
$ 64.00
Quick view
Trackside Dress
$ 62.00
Quick view
Velma Dress
$ 60.00
Sold Out
Peakview Dress
$ 74.00
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
Quick view
Nina Dress
$ 48.00
Quick view
Wide Awake Dress
$ 66.00
Quick view
Existing Dress
$ 60.00
Sold Out
Erin Skirt
$ 50.00
Quick view
Maria Dress
$ 50.00
Sold Out
Lark Dress
$ 54.00
Quick view
Margo Dress
$ 72.00
Quick view
Santana Dress
$ 78.00
Quick view
Salem Dress
$ 68.00
Sold Out
Coastal Bliss Dress
$ 74.00
Quick view
Next Mistake Skirt
$ 48.00
Sold Out
Amour Dress
$ 70.00
Sale
Quick view
Almost Famous Skirt
Regular price $ 38.00 Sale price$ 30.00 Save $ 8.00
Quick view
My Lover Dress
$ 50.00
Sold Out
Kiss Me At Midnight Dress
Regular price $ 44.00 Sale price$ 30.00 Save $ 14.00
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.
Trackside Dress
Trackside Dress
Trackside Dress
Trackside Dress
Trackside Dress
Trackside Dress
Trackside Dress
Trackside Dress
Trackside Dress
Trackside Dress
Trackside Dress
Trackside Dress
Trackside Dress
Trackside Dress
Trackside Dress
Trackside Dress
Trackside Dress
Trackside Dress
Trackside Dress
Trackside Dress
Trackside Dress
Trackside Dress
Trackside Dress
Trackside Dress
Trackside Dress
Trackside Dress
Trackside Dress
Trackside Dress
Trackside Dress
Trackside Dress
Trackside Dress
Trackside Dress

Trackside Dress

Regular price $ 62.00 Save $ -62.00
/

  • Fall Keeneland season is here and this gorgeous maxi dress is just what you need. This sweater dress is the perfect addition to every fall closet!
  • 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.
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
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  • 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.
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. 

 

Nina Dress
Nina Dress
Nina Dress
Nina Dress
Nina Dress
Nina Dress
Nina Dress
Nina Dress
Nina Dress
Nina Dress
Nina Dress
Nina Dress
Nina Dress
Nina Dress
Nina Dress
Nina Dress
Nina Dress
Nina Dress
Nina Dress
Nina Dress

Nina Dress

Regular price $ 48.00 Save $ -48.00
/

  • 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.
Wide Awake Dress
Wide Awake Dress
Wide Awake Dress
Wide Awake Dress
Wide Awake Dress
Wide Awake Dress
Wide Awake Dress
Wide Awake Dress
Wide Awake Dress
Wide Awake Dress
Wide Awake Dress
Wide Awake Dress
Wide Awake Dress
Wide Awake Dress
Wide Awake Dress
Wide Awake Dress
Wide Awake Dress
Wide Awake Dress
Wide Awake Dress
Wide Awake Dress
Wide Awake Dress
Wide Awake Dress

Wide Awake Dress

Regular price $ 66.00 Save $ -66.00
/

    • 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. 
Existing Dress
Existing Dress
Existing Dress
Existing Dress
Existing Dress
Existing Dress
Existing Dress
Existing Dress
Existing Dress
Existing Dress

Existing Dress

Regular price $ 60.00 Save $ -60.00
/

  • 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. 
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
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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.
Margo Dress
Margo Dress
Margo Dress
Margo Dress
Margo Dress
Margo Dress
Margo Dress
Margo Dress
Margo Dress
Margo Dress
Margo Dress
Margo Dress
Margo Dress
Margo Dress
Margo Dress
Margo Dress
Margo Dress
Margo Dress

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.
Santana Dress
Santana Dress
Santana Dress
Santana Dress
Santana Dress
Santana Dress
Santana Dress
Santana Dress
Santana Dress
Santana Dress
Santana Dress
Santana Dress
Santana Dress
Santana Dress
Santana Dress
Santana Dress
Santana Dress
Santana Dress
Santana Dress
Santana Dress

Santana Dress

Regular price $ 78.00 Save $ -78.00
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  • Fall Keeneland season is coming up and this gorgeous maxi dress is just what you need. With different shades and hues of pink florals and ruffles at the bottom, you'll be sure to stand out in our Santana Dress!
  • 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.
Salem Dress
Salem Dress
Salem Dress
Salem Dress
Salem Dress
Salem Dress
Salem Dress
Salem Dress
Salem Dress
Salem Dress
Salem Dress
Salem Dress
Salem Dress
Salem Dress
Salem Dress
Salem Dress

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!
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
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  • 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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