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  • FESTIVAL EDIT
  • New
    New Tops
    Going Out Tops
    Sweaters
    Leather Top
    Corset Top
    New Bottoms
    Jeans
    Shorts
    Skirts
    Pants
    New Dresses
    Going Out
    Midi
    LBD
    LWD
    New Outerwear
    Leather Jackets
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    Moto Jackets
    Blazers
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    Custom Accessories
    Custom Hats
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  • KY COLLECTION
    • KY
    • LEX
  • Accessories
    Jewelry
    Water Resistant Jewelry
    Calypso Custom Jewelry
    Necklaces
    Earrings
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  • FAN FAVS
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Questions? Call (859) 225-3810
LOCAL PICKUP AVAILABLE AT CHECKOUT!
Orders with shoes: $7.95 SHIPPING CHARGE
Questions? Call (859) 225-3810
LOCAL PICKUP AVAILABLE AT CHECKOUT!
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Triple Crown Crew
$ 62.00
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KY Racing Crew
$ 64.00
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KY Classic Mockneck
$ 58.00
Sold Out
Calypso Equine Short
$ 25.00
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Calypso Equine Crew
$ 68.00
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Equine Club Hoodie
$ 48.00
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No Place Like Home Sweatshirt
$ 48.00
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Throwback Crew
$ 52.00
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Varsity Crew - Navy
$ 46.00
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All Roads Lead To KY Hoodie
$ 54.00
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End Game Windbreaker
$ 68.00
Quick view
Lex Tradition Hoodie
$ 42.00
Quick view
Meet Your Match Crew
$ 66.00
Quick view
Spread the Love Crew
$ 52.00
Quick view
Life In KY Hoodie
$ 40.00
Triple Crown Crew
Triple Crown Crew
Triple Crown Crew
Triple Crown Crew
Triple Crown Crew
Triple Crown Crew
Triple Crown Crew
Triple Crown Crew
Triple Crown Crew
Triple Crown Crew
Triple Crown Crew
Triple Crown Crew
Triple Crown Crew
Triple Crown Crew
Triple Crown Crew
Triple Crown Crew
Triple Crown Crew
Triple Crown Crew
Triple Crown Crew
Triple Crown Crew
Triple Crown Crew
Triple Crown Crew
Triple Crown Crew
Triple Crown Crew
Triple Crown Crew
Triple Crown Crew
Triple Crown Crew
Triple Crown Crew
Triple Crown Crew
Triple Crown Crew
Triple Crown Crew
Triple Crown Crew

Triple Crown Crew

Regular price $ 62.00 Save $ -62.00
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  • Our version of a love letter to Kentucky, the sweetest custom! This buttery soft crew has a NAVY double lined neckline and sleeve cuff! The beautiful detailed embroidered design on the front is giving all the vintage Keeneland vibes. Just in time for the spring season!!
  • 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 oversized!
KY Racing Crew
KY Racing Crew
KY Racing Crew
KY Racing Crew
KY Racing Crew
KY Racing Crew
KY Racing Crew
KY Racing Crew
KY Racing Crew
KY Racing Crew
KY Racing Crew
KY Racing Crew
KY Racing Crew
KY Racing Crew
KY Racing Crew
KY Racing Crew
KY Racing Crew
KY Racing Crew
KY Racing Crew
KY Racing Crew
KY Racing Crew
KY Racing Crew
KY Racing Crew
KY Racing Crew
KY Racing Crew
KY Racing Crew
KY Racing Crew
KY Racing Crew
KY Racing Crew
KY Racing Crew

KY Racing Crew

Regular price $ 64.00 Save $ -64.00
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    • The custom for the cool girls.... this Kentucky blue crewneck with cream paneling is your new every day piece. Embroidered "Kentucky Culture" in cream across the front to match the ppaneling 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 long.
KY Classic Mockneck
KY Classic Mockneck
KY Classic Mockneck
KY Classic Mockneck
KY Classic Mockneck
KY Classic Mockneck
KY Classic Mockneck
KY Classic Mockneck
KY Classic Mockneck
KY Classic Mockneck
KY Classic Mockneck
KY Classic Mockneck
KY Classic Mockneck
KY Classic Mockneck
KY Classic Mockneck
KY Classic Mockneck
KY Classic Mockneck
KY Classic Mockneck
KY Classic Mockneck
KY Classic Mockneck
KY Classic Mockneck
KY Classic Mockneck
KY Classic Mockneck
KY Classic Mockneck

KY Classic Mockneck

Regular price $ 58.00 Save $ -58.00
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  • Our take on the VIRAL crewneck trend... this navy mockneck is buttery soft and has "Kentucky" across the front with a heather grey material. 
  • Model 1 is 5'8 with a 33" bust, 27" waist, 33" hips, and wearing a medium.
  • Model 2 is 5'4  with a 32C, 28" waist, 38" hips, and is wearing a small.
  • Model 3 in studio is 5'6" with a 32DD bust, 27" waist, 36" hips, and wearing a medium. This item runs true to size.

 

Calypso Equine Crew
Calypso Equine Crew
Calypso Equine Crew
Calypso Equine Crew
Calypso Equine Crew
Calypso Equine Crew
Calypso Equine Crew
Calypso Equine Crew
Calypso Equine Crew
Calypso Equine Crew
Calypso Equine Crew
Calypso Equine Crew
Calypso Equine Crew
Calypso Equine Crew
Calypso Equine Crew
Calypso Equine Crew
Calypso Equine Crew
Calypso Equine Crew
Calypso Equine Crew
Calypso Equine Crew

Calypso Equine Crew

Regular price $ 68.00 Save $ -68.00
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  • It wouldn't be a Calypso collection without the CUTEST sweat set. This unisex heather grey crew with a navy embroidered design is giving timeless. She's definitely a piece you're going to want to save for your kids. 
  • Pair with our custom shorts and navy hat for the PERFECT look.
  • Katie is 5'10" with a 32" bust, 25" waist, 34" hips, and is wearing a medium for an oversized fit.
  • Katie typically wears a size 2.
Equine Club Hoodie
Equine Club Hoodie
Equine Club Hoodie
Equine Club Hoodie
Equine Club Hoodie
Equine Club Hoodie
Equine Club Hoodie
Equine Club Hoodie
Equine Club Hoodie
Equine Club Hoodie
Equine Club Hoodie
Equine Club Hoodie
Equine Club Hoodie
Equine Club Hoodie
Equine Club Hoodie
Equine Club Hoodie
Equine Club Hoodie
Equine Club Hoodie
Equine Club Hoodie
Equine Club Hoodie
Equine Club Hoodie
Equine Club Hoodie
Equine Club Hoodie
Equine Club Hoodie
Equine Club Hoodie
Equine Club Hoodie
Equine Club Hoodie
Equine Club Hoodie

Equine Club Hoodie

Regular price $ 48.00 Save $ -48.00
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  • Our fav collection yet is HERE! This custom Calypso hoodie is the perfect loungewear piece for fall. 3-D Printed design on front and the back.
  • Pair with jeans and a blazer for an edgier look like Katie, or with sweats for a lazy day at home!
  • Katie is 5'10" with a 32" bust, 25" waist, 34" hips, and is wearing a medium.
  • Katie typically wears a size 2.
No Place Like Home Sweatshirt
No Place Like Home Sweatshirt
No Place Like Home Sweatshirt
No Place Like Home Sweatshirt
No Place Like Home Sweatshirt
No Place Like Home Sweatshirt
No Place Like Home Sweatshirt
No Place Like Home Sweatshirt
No Place Like Home Sweatshirt
No Place Like Home Sweatshirt
No Place Like Home Sweatshirt
No Place Like Home Sweatshirt
No Place Like Home Sweatshirt
No Place Like Home Sweatshirt
No Place Like Home Sweatshirt
No Place Like Home Sweatshirt
No Place Like Home Sweatshirt
No Place Like Home Sweatshirt
No Place Like Home Sweatshirt
No Place Like Home Sweatshirt
No Place Like Home Sweatshirt
No Place Like Home Sweatshirt

No Place Like Home Sweatshirt

Regular price $ 48.00 Save $ -48.00
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  • The Calypso customs just. keep. coming. This new embroidered sweatshirt is a piece of a custom set that perfectly matches our "No Place Like Home Short".
  • The light blue ribbed trim on the neck, waist, and wrists are the CUTEST pops of color on this sweatshirt!
  • Featuring "Lexington Local", "No Place Like Home" & "Kentucky" all on the front in charcoal grey and light blue embroidery.
  • A soft inside & oversized fit - the most fabulous combination in a lounge set!!
  • Model is 5'6" with a 32DD bust, 27" waist, 36" hips, and wearing a large for an oversized look.
  • Model usually wears size 2/4.
  • This item runs slightly oversized.
Throwback Crew
Throwback Crew
Throwback Crew
Throwback Crew
Throwback Crew
Throwback Crew
Throwback Crew
Throwback Crew
Throwback Crew
Throwback Crew
Throwback Crew
Throwback Crew
Throwback Crew
Throwback Crew
Throwback Crew
Throwback Crew
Throwback Crew
Throwback Crew
Throwback Crew
Throwback Crew
Throwback Crew
Throwback Crew
Throwback Crew
Throwback Crew
Throwback Crew
Throwback Crew
Throwback Crew
Throwback Crew
Throwback Crew
Throwback Crew
Throwback Crew
Throwback Crew
Throwback Crew
Throwback Crew

Throwback Crew

Regular price $ 52.00 Save $ -52.00
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  • The oversized crew of our DREAMS!! This vintage style Kentucky sweatshirt is perfect for lover of all things bluegrass!
  • Pair with jeans or leggings for an elevated comfy look!
  • Featuring the navy and white striped cuffs, neckline & waistline.
  • A navy "Kentucky" & "Bluegrass State" embroidered design on the front against a heather white base.
  • Model is 5'6" with a 32DD bust, 27" waist, 36" hips, and wearing a large for an oversized look.
  • Model usually wears size 2/4.
  • This item runs slightly big!
Varsity Crew - Navy
Varsity Crew - Navy
Varsity Crew - Navy
Varsity Crew - Navy
Varsity Crew - Navy
Varsity Crew - Navy
Varsity Crew - Navy
Varsity Crew - Navy
Varsity Crew - Navy
Varsity Crew - Navy
Varsity Crew - Navy
Varsity Crew - Navy
Varsity Crew - Navy
Varsity Crew - Navy

Varsity Crew - Navy

Regular price $ 46.00 Save $ -46.00
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  • Calypso in-house design! Navy unisex crew sweatshirt with white outline Kentucky embroidery.
  • 50% cotton, 50% polyester pre-shrunk fleece
  • 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.
All Roads Lead To KY Hoodie
All Roads Lead To KY Hoodie
All Roads Lead To KY Hoodie
All Roads Lead To KY Hoodie
All Roads Lead To KY Hoodie
All Roads Lead To KY Hoodie
All Roads Lead To KY Hoodie
All Roads Lead To KY Hoodie
All Roads Lead To KY Hoodie
All Roads Lead To KY Hoodie
All Roads Lead To KY Hoodie
All Roads Lead To KY Hoodie
All Roads Lead To KY Hoodie
All Roads Lead To KY Hoodie
All Roads Lead To KY Hoodie
All Roads Lead To KY Hoodie
All Roads Lead To KY Hoodie
All Roads Lead To KY Hoodie
All Roads Lead To KY Hoodie
All Roads Lead To KY Hoodie
All Roads Lead To KY Hoodie
All Roads Lead To KY Hoodie
All Roads Lead To KY Hoodie
All Roads Lead To KY Hoodie
All Roads Lead To KY Hoodie
All Roads Lead To KY Hoodie
All Roads Lead To KY Hoodie
All Roads Lead To KY Hoodie

All Roads Lead To KY Hoodie

Regular price $ 54.00 Save $ -54.00
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  • A NEW fav Calypso custom just hit the floor and is an edgier look for our Kentucky lovers -- a puff ink print design on the back & screen print on the front. 
  • The front: "Kentucky Culture Established 1792"
  • The back: "All Roads Lead To Kentucky"
  • Model is 5'6" with a 32DD bust, 27" waist, 36" hips, and wearing a large.
  • Recommended: Wash inside out on a cold cycle, do not tumble dry, do not iron over print! 
End Game Windbreaker
End Game Windbreaker
End Game Windbreaker
End Game Windbreaker
End Game Windbreaker
End Game Windbreaker
End Game Windbreaker
End Game Windbreaker
End Game Windbreaker
End Game Windbreaker
End Game Windbreaker
End Game Windbreaker
End Game Windbreaker
End Game Windbreaker
End Game Windbreaker
End Game Windbreaker
End Game Windbreaker
End Game Windbreaker
End Game Windbreaker
End Game Windbreaker
End Game Windbreaker
End Game Windbreaker
End Game Windbreaker
End Game Windbreaker
End Game Windbreaker
End Game Windbreaker
End Game Windbreaker
End Game Windbreaker
End Game Windbreaker
End Game Windbreaker
End Game Windbreaker
End Game Windbreaker

End Game Windbreaker

Regular price $ 68.00 Save $ -68.00
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  • A Calypso CUSTOM windbreaker just dropped...
  • This black windbreaker has a dark grey embroidery on the chest & stripes on the cuffs and neckline, as well as grey paneling along each side. 
  • "Kentucky Est. 1792" fine line embroidery. 
  • Drawstring adjustable cinch at the bottom. Zippered side for extra breathable room at the bottom.
  • Female model is 5'5" with a 34 bust, 26" waist, 32" hips, and wearing a medium.
  • Male model is 6'0" with a 32" waist and is wearing a large.
  • This item runs true to size.
Lex Tradition Hoodie
Lex Tradition Hoodie
Lex Tradition Hoodie
Lex Tradition Hoodie
Lex Tradition Hoodie
Lex Tradition Hoodie
Lex Tradition Hoodie
Lex Tradition Hoodie
Lex Tradition Hoodie
Lex Tradition Hoodie
Lex Tradition Hoodie
Lex Tradition Hoodie
Lex Tradition Hoodie
Lex Tradition Hoodie
Lex Tradition Hoodie
Lex Tradition Hoodie
Lex Tradition Hoodie
Lex Tradition Hoodie
Lex Tradition Hoodie
Lex Tradition Hoodie
Lex Tradition Hoodie
Lex Tradition Hoodie

Lex Tradition Hoodie

Regular price $ 42.00 Save $ -42.00
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CHARLIE + CLAIRE'S X CALYPSO COLLAB

  • Say HELLO to our final tribute to the best selling "MEET ME ON STATE STREET" Hoodie, but with a charlie + claire's FLARE! 
  • This perfectly oversized charcoal custom with off-white puff ink on the front and back will be the best addition to your hoodie collection!
  • Pair with boyfriend jeans, parachute pants, or a printed bottom! 
  • Model 1: 5'4" with a 34D bust, 34" waist, 42" hips, and wearing an XL.
  • Model 2: 5'6" with a 32DD bust, 27" waist, 36" hips, and wearing an XL.
  • Recommended: Wash inside out on a cold cycle, do not tumble dry, do not iron over print! 
Meet Your Match Crew
Meet Your Match Crew
Meet Your Match Crew
Meet Your Match Crew
Meet Your Match Crew
Meet Your Match Crew
Meet Your Match Crew
Meet Your Match Crew
Meet Your Match Crew
Meet Your Match Crew
Meet Your Match Crew
Meet Your Match Crew
Meet Your Match Crew
Meet Your Match Crew
Meet Your Match Crew
Meet Your Match Crew
Meet Your Match Crew
Meet Your Match Crew
Meet Your Match Crew
Meet Your Match Crew
Meet Your Match Crew
Meet Your Match Crew

Meet Your Match Crew

Regular price $ 66.00 Save $ -66.00
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COUNTRY CLUB COLLECTION -- Newest Calypso Customs!

  • Down for doubles? Show off your inner country club tennis style with our custom crew!! Featuring our "Kentucky Culture" across the front in navy.
  • 90% cotton/10% polyester blend
  • Low pill, high density fabric for a long lasting product
  • Model is 5'6" with a 32DD bust, 27" waist, 36" hips, and wearing a large for an oversized fit. 
  • This item runs oversized!
Spread the Love Crew
Spread the Love Crew
Spread the Love Crew
Spread the Love Crew
Spread the Love Crew
Spread the Love Crew
Spread the Love Crew
Spread the Love Crew
Spread the Love Crew
Spread the Love Crew
Spread the Love Crew
Spread the Love Crew
Spread the Love Crew
Spread the Love Crew
Spread the Love Crew
Spread the Love Crew
Spread the Love Crew
Spread the Love Crew
Spread the Love Crew
Spread the Love Crew
Spread the Love Crew
Spread the Love Crew
Spread the Love Crew
Spread the Love Crew
Spread the Love Crew
Spread the Love Crew

Spread the Love Crew

Regular price $ 52.00 Save $ -52.00
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  • NEW CALYPSO CUSTOM -- the perfect oversized sweatshirt in oatmeal heather! "Treat Others With Kindness" puff screen print across the front and the back in green. Pair with joggers or biker shorts for the summer and spread the love!
  • 80% cotton, 20% polyester
  • Image 2: Model is 5'6 wearing size XL
  • Image 3: Model is 5'2 wearing size Medium
  • Image 5: Model is 5'0 wearing size Medium
  • Image 8: Model is 5'6 wearing size Large
  • This item runs oversized
  • Recommended: Wash inside out on a cold wash, do not tumble dry, do not iron over print!
Life In KY Hoodie
Life In KY Hoodie
Life In KY Hoodie
Life In KY Hoodie
Life In KY Hoodie
Life In KY Hoodie
Life In KY Hoodie
Life In KY Hoodie
Life In KY Hoodie
Life In KY Hoodie

Life In KY Hoodie

Regular price $ 40.00 Save $ -40.00
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  • Another Calypso custom design!
  • Trendy natural colored unisex hoodie with black screen print!
  • Small offset "KENTUCKY" front with a large "Life In KY" back design. 
  • 100% cotton 
  • Model is 5'6" with a 32DD bust, 27" waist, 36" hips, and wearing XL for an oversized look.

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