Insulated Coolers

"You can bring the party, literally. These soft coolers fit everything you need - from lunch to picnic essentials - to the perfect 30 of beer..." Never leave the house again without your cooler from Whimsicality!
78 results
Pleasure Chest Picnic Cooler - "Catch of the Day" SUM24
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Pleasure Chest Picnic Cooler - "Catch of the Day" SUM24
$38.00
Pleasure Chest Picnic Cooler - "Clawsome" SUM24
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Pleasure Chest Picnic Cooler - "Clawsome" SUM24
$38.00
Pleasure Chest Picnic Cooler - "David Checkham" SIG21
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Pleasure Chest Picnic Cooler - "David Checkham" SIG21
$38.00
Pleasure Chest Picnic Cooler - "Exclusive Anchor Management" DSE
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Pleasure Chest Picnic Cooler - "Exclusive Anchor Management" DSE
$38.50
Pleasure Chest Picnic Cooler - "Exclusive Annapolis at Whimsicality"
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Pleasure Chest Picnic Cooler - "Exclusive Annapolis at Whimsicality"
$38.50
Pleasure Chest Picnic Cooler - "Friend of Dorothy" SP24
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Pleasure Chest Picnic Cooler - "Friend of Dorothy" SP24
$38.00
Pleasure Chest Picnic Cooler - "Fronds with Benefits" SP24
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Pleasure Chest Picnic Cooler - "Fronds with Benefits" SP24
$38.00
Pleasure Chest Picnic Cooler - "Fruit of Tulum" SUM24
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Pleasure Chest Picnic Cooler - "Fruit of Tulum" SUM24
$38.00
Pleasure Chest Picnic Cooler - "Lattice Knight" SP24
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Pleasure Chest Picnic Cooler - "Lattice Knight" SP24
$38.00
Pleasure Chest Picnic Cooler - "Mademoishell" SUM23
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Pleasure Chest Picnic Cooler - "Mademoishell" SUM23
$38.00
Pleasure Chest Picnic Cooler - "Maryland" Statement!
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Pleasure Chest Picnic Cooler - "Maryland" Statement!
$38.50
Pleasure Chest Picnic Cooler - "Off the Grid" SUM24
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Pleasure Chest Picnic Cooler - "Off the Grid" SUM24
$38.00
Pleasure Chest Picnic Cooler - "Sand Holla" SUM24
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Pleasure Chest Picnic Cooler - "Sand Holla" SUM24
$38.00
Pleasure Chest Picnic Cooler - "Shellebrity" ENCORE23
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Pleasure Chest Picnic Cooler - "Shellebrity" ENCORE23
$38.00
Pleasure Chest Picnic Cooler - "Ship Shape" SIG21
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Pleasure Chest Picnic Cooler - "Ship Shape" SIG21
$38.00
Pleasure Chest Picnic Cooler - "Sucker Punch" SP24
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Pleasure Chest Picnic Cooler - "Sucker Punch" SP24
$38.00
Pleasure Chest Picnic Cooler - "Sunny Side Up" SUM24
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Pleasure Chest Picnic Cooler - "Sunny Side Up" SUM24
$38.00
Pleasure Chest Picnic Cooler - "Totes Ma Boat" SP24
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Pleasure Chest Picnic Cooler - "Totes Ma Boat" SP24
$38.00
Pleasure Chest Picnic Cooler - "Washington, DC" Statement!
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Pleasure Chest Picnic Cooler - "Washington, DC" Statement!
$38.50
SIDEWALK SALE ITEM - Cool Horizons Large Cooler - "Grain Teaser" F23
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SIDEWALK SALE ITEM - Cool Horizons Large Cooler - "Grain Teaser" F23
$56.00 $80.00
SIDEWALK SALE ITEM - Cool Horizons Large Cooler - "Hot Tropic" SUM23
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SIDEWALK SALE ITEM - Cool Horizons Large Cooler - "Hot Tropic" SUM23
$56.00 $80.00
SIDEWALK SALE ITEM - Cools Gold Soft Cooler - "Hot Tropic" SUM23
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SIDEWALK SALE ITEM - Cools Gold Soft Cooler - "Hot Tropic" SUM23
$50.00 $72.00
SIDEWALK SALE ITEM - Cools Gold Soft Cooler - "VANILLA + Lovers Lane" SP24
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SIDEWALK SALE ITEM - Cools Gold Soft Cooler - "VANILLA + Lovers Lane" SP24
$57.00 $82.00
SIDEWALK SALE ITEM - LARGE Eloise Lunch Cooler - "Scarf Vader" H23
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SIDEWALK SALE ITEM - LARGE Eloise Lunch Cooler - "Scarf Vader" H23
$39.00 $56.00
SIDEWALK SALE ITEM - Nooner Lunch Cooler - "Kilted Age" F23
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SIDEWALK SALE ITEM - Nooner Lunch Cooler - "Kilted Age" F23
$18.00 $30.00
SIDEWALK SALE ITEM - Play It Cool Backpack Cooler - "Croquet Monsieur" SUM23
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SIDEWALK SALE ITEM - Play It Cool Backpack Cooler - "Croquet Monsieur" SUM23
$52.00 $75.00
SIDEWALK SALE ITEM - Pleasure Chest Picnic Cooler - "Hot Tropic" SUM23
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SIDEWALK SALE ITEM - Pleasure Chest Picnic Cooler - "Hot Tropic" SUM23
$26.00 $38.00
SIDEWALK SALE ITEM - Pleasure Chest Picnic Cooler - "Prep Talk" F23
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SIDEWALK SALE ITEM - Pleasure Chest Picnic Cooler - "Prep Talk" F23
$26.00 $38.00
Spirit Chillah Insulated Wine Cooler Bag - "Fruit of Tulum" SUM24
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Spirit Chillah Insulated Wine Cooler Bag - "Fruit of Tulum" SUM24
$19.50
Spirit Chillah Insulated Wine Cooler Bag - "Ikant Belize" SUM24
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Spirit Chillah Insulated Wine Cooler Bag - "Ikant Belize" SUM24
$19.50
Spirit Chillah Insulated Wine Cooler Bag - "Sunny Side Up" SUM24
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Spirit Chillah Insulated Wine Cooler Bag - "Sunny Side Up" SUM24
$19.50
The Stiff One Large Cooler - "Anchor Issues" ENCORE23
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Only 3 left!
The Stiff One Large Cooler - "Anchor Issues" ENCORE23
$56.00
The Stiff One Large Cooler - "Catch of the Day" SUM24
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Only 2 left!
The Stiff One Large Cooler - "Catch of the Day" SUM24
$56.00
The Stiff One Large Cooler - "Exclusive Annapolis at Whimsicality"
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The Stiff One Large Cooler - "Exclusive Annapolis at Whimsicality"
$60.00
The Stiff One Large Cooler - "Fleetwood Black" SIG21
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The Stiff One Large Cooler - "Fleetwood Black" SIG21
$56.00
The Stiff One Large Cooler - "Odyssea" SUM24
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The Stiff One Large Cooler - "Odyssea" SUM24
$56.00
78 results
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