Men's Shorts: From Seersucker to Madras & Knee Length to Bare Thighs

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Traditional Madras Shorts by Country Club Prep
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$ 120.00
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$ 120.00
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Montauk Madras Shorts by Country Club Prep
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$ 120.00
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$ 120.00
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Cotuit Madras Shorts by Country Club Prep
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$ 120.00
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$ 120.00
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Vineyard Madras Shorts by Country Club Prep
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$ 120.00
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$ 120.00
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Pastel Patchwork Madras Shorts by Country Club Prep
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$ 120.00
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$ 120.00
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Blue Seersucker Shorts by Country Club Prep
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$ 120.00
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$ 120.00
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Tan Seersucker Shorts by Country Club Prep
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$ 120.00
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$ 120.00
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Red Seersucker Shorts by Country Club Prep
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$ 120.00
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$ 120.00
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The Charlottesville Orange Short by Country Club Prep
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$ 69.00
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$ 69.00
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Orange Seersucker Shorts by Country Club Prep
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$ 120.00
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$ 120.00
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Pink Seersucker Shorts by Country Club Prep
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$ 120.00
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$ 120.00
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Cisco Short in Hingham Patch Madras by Castaway Clothing
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$ 118.00
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$ 118.00
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Cisco Short in Osterville Patch Madras by Castaway Clothing
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$ 118.00
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$ 118.00
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The Broad Street Linen Short by Country Club Prep
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$ 95.00
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$ 95.00
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Gingham Party Panel Cisco Short by Castaway Clothing
Regular Price
$ 118.00
Sale Price
$ 118.00
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$ 118.00
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Embroidered Cisco Shorts Blue Seersucker with Martini Glasses by Castaway Clothing
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$ 110.00
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$ 110.00
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Stretch Twill Cisco Short with Tee Time in Liberty by Castaway Clothing
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$ 110.00
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$ 110.00
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$ 110.00
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Stretch Twill Cisco Short with Fin & Tonic in Navy by Castaway Clothing
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$ 110.00
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$ 110.00
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$ 110.00
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Island Canvas Short with Tequila, Salt & Lime in Dark Denim by Castaway Clothing
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$ 110.00
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$ 110.00
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$ 110.00
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The Captain Shorts in Grey by Country Club Prep
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$ 85.00
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$ 85.00
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Cross Country PREP-Formance 9.5" Short by Johnnie-O
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$ 98.00
Sale Price
$ 98.00
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$ 98.00
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Stretch Twill Cisco Short with Shamrocks in Nantucket Navy by Castaway Clothing
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$ 110.00
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$ 110.00
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Heather T3 Gulf Short by Southern Tide
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$ 85.00
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$ 85.00
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Neal Stretch Twill Shorts by Johnnie-O
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$ 79.00
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$ 79.00
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The Skipjack 9" Short in Stone by Southern Tide
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$ 85.00
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$ 85.00
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T3 Brrrº Gulf Performance Short by Southern Tide
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$ 99.50
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$ 99.50
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Tonal Seersucker Skipjack Short by Southern Tide
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$ 89.50
Sale Price
$ 89.50
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Fishing Shorts in Vivid Blue by AFTCO
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$ 55.00
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$ 55.00
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Pot Leaf Stretch Twill Cisco Short in Slate by Castaway Clothing
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$ 98.00
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$ 98.00
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Leeward Print Cisco Short with by Castaway Clothing
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$ 118.00
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$ 118.00
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Tide to Trail Performance Shorts in Heron Green by Southern Tide
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$ 79.50
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$ 79.50
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The Skipjack 9" Short in Sandstone Khaki by Southern Tide
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$ 85.00
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$ 85.00
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The 9" Skipjack Short in True Navy by Southern Tide
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$ 85.00
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$ 85.00
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Backrush Heather Lounge Short by Southern Tide
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$ 69.50
Sale Price
$ 69.50
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Stretch Twill Cisco Short with Surfing Santa by Castaway Clothing
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$ 98.00
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$ 98.00
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Mini Gingham Shorts in Royal Blue by Country Club Prep
Regular Price
$ 120.00
Sale Price
$ 120.00
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Once upon a time, there was a kingdom full of prepsters called Shortsteros. Its four clans — House Seersucker, House Linen, House Madras and House Chino — constantly quarreled over whose men’s shorts should rule the kingdom, for they were equally as handsome and preppy as the next.

 “Seersucker should be the short of the land,” exclaimed Lord Seersucker, “for its petite pastel stripes in blue, pink, gray and yellow bring out the seaside prep in all gentlemen.” Lord Linen disagreed: “Linen shorts are clearly superior, dear sir, for they are light and protect all wearers against our sacred dragon enemy, Chafing.” Lord Madras interjected, “You are forgetting the strong, fine fabric and trendy plaid patterns that are the madras short, a short fit for a king!” “You’re all wrong,” said Lord Chino, “for none of these shorts are match for the classic twill chino.”

The row went on for years, until one day a knight rode into the kingdom bearing the emblem of a fox. “I am Sir Longshanks,” he told the lords, “and I propose all the men in the land have access to all of your shorts. This kingdom is built on preppiness, and who are you to deny this of them? I say all bros shall be able to wear all sizes, lengths and colors of shorts at all times.” The idea was a revelation and the lords were overjoyed with Longshanks’ stroke of genius. Shortly thereafter they named Sir Longshanks their king and adopted Country Club Prep as the new name of their kingdom, where guys have been shopping for all kinds of preppy shorts ever since. And they all lived preppily ever after.