Spring 2024 Preppy New Arrivals for Men & Women

59 products

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Stretch Twill Harbor Pant with Embroidered Football and Turkey by Castaway Clothing
Regular Price
$ 148.00
Sale Price
$ 148.00
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Stretch Twill Cisco Short with Tee Time in Liberty by Castaway Clothing
Regular Price
$ 110.00
Sale Price
$ 110.00
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$ 110.00
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Stretch Twill Cisco Short with Fin & Tonic in Navy by Castaway Clothing
Regular Price
$ 110.00
Sale Price
$ 110.00
Regular Price
$ 110.00
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Island Canvas Short with Tequila, Salt & Lime in Dark Denim by Castaway Clothing
Regular Price
$ 110.00
Sale Price
$ 110.00
Regular Price
$ 110.00
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Gingham Party Panel Cisco Short by Castaway Clothing
Regular Price
$ 118.00
Sale Price
$ 118.00
Regular Price
$ 118.00
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per 
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 
Spinnaker Blazer With Embroidered White Anchor in Blue Grotto by Castaway Clothing
Regular Price
$ 325.00
Sale Price
$ 325.00
Regular Price
$ 325.00
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Cisco Short in Hingham Patch Madras by Castaway Clothing
Regular Price
$ 118.00
Sale Price
$ 118.00
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Cisco Short in Osterville Patch Madras by Castaway Clothing
Regular Price
$ 118.00
Sale Price
$ 118.00
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per 
Cisco Short in Red, White, and Blue Seersucker by Castaway Clothing
Regular Price
$ 89.50
Sale Price
$ 89.50
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Leeward Print Cisco Short with by Castaway Clothing
Regular Price
$ 118.00
Sale Price
$ 118.00
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Sandbar Swimsuit with Embroidered Fin & Tonic by Castaway Clothing
Regular Price
$ 95.00
Sale Price
$ 95.00
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Save 40%
Spinnaker Blazer With Embroidered White Anchor in Seagrass by Castaway Clothing
Regular Price
$ 195.00
Sale Price
$ 195.00
Regular Price
$ 325.00
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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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Sleeper Pant with Martini Candy Cane by Castaway Clothing
Regular Price
$ 78.00
Sale Price
$ 78.00
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per 
Stretch Twill Cisco Short with Surfing Santa by Castaway Clothing
Regular Price
$ 98.00
Sale Price
$ 98.00
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per 
Martini Candy Cane Beachcomber Corduroy Pant by Castaway Clothing
Regular Price
$ 175.00
Sale Price
$ 175.00
Regular Price
$ 175.00
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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
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per 
Stretch Twill Tunic Dress in Royal Stewart Plaid with Velvet Trim by Castaway Clothing
Regular Price
$ 178.00
Sale Price
$ 178.00
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Ali Corduroy Skirt with Embroidered Woody & Christmas Trees by Castaway Clothing
Regular Price
$ 125.00
Sale Price
$ 125.00
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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
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per 
Stretch Twill Harbor Pant in Blackwatch Tartan Plaid by Castaway Clothing
Regular Price
$ 148.00
Sale Price
$ 148.00
Regular Price
$ 148.00
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
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Pot Leaf Stretch Twill Cisco Short in Slate by Castaway Clothing
Regular Price
$ 98.00
Sale Price
$ 98.00
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Unit Price
per 
Stretch Twill Cisco Short with Shamrocks in Nantucket Navy by Castaway Clothing
Regular Price
$ 110.00
Sale Price
$ 110.00
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per 
Cisco Short in Royal & Navy Seersucker by Castaway Clothing
Regular Price
$ 78.00
Sale Price
$ 78.00
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Ohana Print Cisco Short by Castaway Clothing
Regular Price
$ 110.00
Sale Price
$ 110.00
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Ali Skirt in Chatham Patch Madras by Castaway Clothing
Regular Price
$ 128.00
Sale Price
$ 128.00
Regular Price
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per 
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 
Stretch Twill Harbor Pant with Embroidered Christmas Trees by Castaway Clothing
Regular Price
$ 148.00
Sale Price
$ 148.00
Regular Price
$ 148.00
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 

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.