Spring 2024 Preppy New Arrivals for Men & Women

45 products

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Stretch Twill Cisco Short with Spicy Margarita by Castaway Clothing
Regular Price
$ 110.00
Sale Price
$ 110.00
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$ 110.00
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Cisco Short in Weston Patch Madras by Castaway Clothing
Regular Price
$ 118.00
Sale Price
$ 118.00
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Cisco Short in Chancellor Patch Madras by Castaway Clothing
Regular Price
$ 118.00
Sale Price
$ 118.00
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Spinnaker Blazer in Grey Lady Patch Madras by Castaway Clothing
Regular Price
$ 345.00
Sale Price
$ 345.00
Regular Price
$ 345.00
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per 
Stretch Twill Cisco Short with Great White Shark by Castaway Clothing
Regular Price
$ 110.00
Sale Price
$ 110.00
Regular Price
$ 110.00
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Stretch Twill Cisco Short with Anchor in White by Castaway Clothing
Regular Price
$ 110.00
Sale Price
$ 110.00
Regular Price
$ 110.00
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Stretch Twill Cisco Short with American Flag in Hurricane Red by Castaway Clothing
Regular Price
$ 110.00
Sale Price
$ 110.00
Regular Price
$ 110.00
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Stretch Twill Harbor Pant with Martini and Shaker by Castaway Clothing
Regular Price
$ 148.00
Sale Price
$ 148.00
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Stretch Twill Harbor Pant with Embroidered Lucky Mint Julep in White by Castaway Clothing
Regular Price
$ 148.00
Sale Price
$ 148.00
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Spinnaker Blazer in Osterville Patch Madras by Castaway Clothing
Regular Price
$ 345.00
Sale Price
$ 345.00
Regular Price
$ 345.00
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per 
Cisco Short in Hingham Patch Madras by Castaway Clothing
Regular Price
$ 118.00
Sale Price
$ 118.00
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Tartan Cross Rip Quilted Vest in Black Stewart by Castaway Clothing
Regular Price
$ 148.00
Sale Price
$ 148.00
Regular Price
$ 148.00
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ACKformance Short with USA Flag in Cement by Castaway Clothing
Regular Price
$ 118.00
Sale Price
$ 118.00
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Unit Price
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Sleeper Pant with Martini Candy Cane by Castaway Clothing
Regular Price
$ 78.00
Sale Price
$ 78.00
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Stretch Twill Cisco Short with Surfing Santa by Castaway Clothing
Regular Price
$ 98.00
Sale Price
$ 98.00
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Unit Price
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Martini Candy Cane Beachcomber Corduroy Pant by Castaway Clothing
Regular Price
$ 175.00
Sale Price
$ 175.00
Regular Price
$ 175.00
Unit Price
per 
Save 48%
Sleeveless Top in Royal Stewart Tartan Plaid by Castaway Clothing
Regular Price
$ 61.95
Sale Price
$ 61.95
Regular Price
$ 118.00
Unit Price
per 
Save 47%
Stretch Twill Ali Skirt in Blackwatch Plaid by Castaway Clothing
Regular Price
$ 65.95
Sale Price
$ 65.95
Regular Price
$ 125.00
Unit Price
per 
Save 47%
Stretch Twill Ali Skirt in Royal Stewart Plaid by Castaway Clothing
Regular Price
$ 65.95
Sale Price
$ 65.95
Regular Price
$ 125.00
Unit Price
per 
Save 48%
Ladies Beachcomber Stretch Twill Ankle Capri in Royal Stewart Tartan Plaid by Castaway Clothing
Regular Price
$ 76.95
Sale Price
$ 76.95
Regular Price
$ 148.00
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per 
Ladies Beachcomber Stretch Corduroy Ankle Capri with Embroidered Christmas Trees by Castaway Clothing
Regular Price
$ 168.00
Sale Price
$ 168.00
Regular Price
$ 168.00
Unit Price
per 
Save 47%
Barefoot Boxer with Embroidered Hangover Special in Blue Oxford by Castaway Clothing
Regular Price
$ 18.95
Sale Price
$ 18.95
Regular Price
$ 36.00
Unit Price
per 
Pot Leaf Stretch Twill Cisco Short in Slate by Castaway Clothing
Regular Price
$ 98.00
Sale Price
$ 98.00
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Cisco Short in Royal & Navy Seersucker by Castaway Clothing
Regular Price
$ 78.00
Sale Price
$ 78.00
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Unit Price
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Ohana Print Cisco Short by Castaway Clothing
Regular Price
$ 110.00
Sale Price
$ 110.00
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Unit Price
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Save 48%
Ladies Button Down Flannel Shirt by Castaway Clothing
Regular Price
$ 61.95
Sale Price
$ 61.95
Regular Price
$ 118.00
Unit Price
per 
Save 48%
Gingham Sleeper Pant with Embroidered Christmas Tree by Castaway Clothing
Regular Price
$ 40.95
Sale Price
$ 40.95
Regular Price
$ 78.00
Unit Price
per 
Save 48%
Chase Long Sleeve Shirt by Castaway Clothing
Regular Price
$ 76.95
Sale Price
$ 76.95
Regular Price
$ 148.00
Unit Price
per 
Save 48%
Cabo Camp Shirt by Castaway Clothing
Regular Price
$ 50.95
Sale Price
$ 50.95
Regular Price
$ 98.00
Unit Price
per 
Save 47%
Sandbar Swimsuit with Embroidered Calico Jack by Castaway Clothing
Regular Price
$ 44.95
Sale Price
$ 44.95
Regular Price
$ 85.00
Unit Price
per 
Save 47%
Straight Wharf Linen Shirt with Embroidered Palm Tree by Castaway Clothing
Regular Price
$ 70.95
Sale Price
$ 70.95
Regular Price
$ 135.00
Unit Price
per 
Save 48%
Chase Short Sleeve Patch Seersucker Shirt by Castaway Clothing
Regular Price
$ 59.95
Sale Price
$ 59.95
Regular Price
$ 115.00
Unit Price
per 
Save 47%
Barefoot Boxer in Seafoam Oxford with Embroidered Coq of the Walk by Castaway Clothing
Regular Price
$ 18.95
Sale Price
$ 18.95
Regular Price
$ 36.00
Unit Price
per 
Save 48%
Sandbar Swimsuit in Koi Pond by Castaway Clothing
Regular Price
$ 40.95
Sale Price
$ 40.95
Regular Price
$ 78.00
Unit Price
per 
Save 48%
Sandbar Swimsuit in Somerset Madras by Castaway Clothing
Regular Price
$ 40.95
Sale Price
$ 40.95
Regular Price
$ 78.00
Unit Price
per 
Beachcomber Corduroy Pants in Crimson with Embroidered Christmas Tree by Castaway Clothing
Regular Price
$ 175.00
Sale Price
$ 175.00
Regular Price
$ 175.00
Unit Price
per 

Shop the latest new preppy styles and brands offered from Country Club Prep. Do we have great brands? You know it! How about Barbour, Sperry, Jack Rogers, Vineyard Vines, Southern Proper, Southern Tide, Southern Marsh, Sail to Sable, Lilly Pulitzer and about 180 more (click here for all brands)? When you think "preppy," there's only one place to go - Country Club Prep. There's a reason we're the best retailer on the web.