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      • Boys' Clothing (Sizes 4 & Up)
        • Selected categoryShorts
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        • Preppy (56) Items (56)
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56 results

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    • PreppyRemove filter
    • Size: 14Remove filter
    • Size: 18Remove filter
    • Fit: Not SpecifiedRemove filter
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    • Boys Tony Hawk Shorts Green Plaid Size 18 Skater Preppy
      Boys Tony Hawk Shorts Green Plaid Size 18 Skater Preppy
      Opens in a new window or tab
      Pre-Owned
      $14.44
      Was: $16.9915% off
      or Best Offer
      Free delivery
      Sponsored
    • Polo Ralph Lauren Bermuda Shorts Kids 18 White Preppy Neutral Spring Summer
      Polo Ralph Lauren Bermuda Shorts Kids 18 White Preppy Neutral Spring Summer
      Opens in a new window or tab
      Pre-Owned
      $19.96
      Was: $24.9520% off
      or Best Offer
      +$6.75 delivery
      Free returns
      Sponsored
      Top Rated Plus
    • Polo Ralph Lauren Blue Drawstring Preppy Shorts Boy's Size 14
      Polo Ralph Lauren Blue Drawstring Preppy Shorts Boy's Size 14
      Opens in a new window or tab
      Pre-Owned
      $15.00
      or Best Offer
      +$7.00 delivery
      Extra 15% off with coupon
      Sponsored
    • NWT Crewcuts Boy’s Stanton Seersucker Chino Shorts Blue White Striped Cotton 14
      NWT Crewcuts Boy’s Stanton Seersucker Chino Shorts Blue White Striped Cotton 14
      Opens in a new window or tab
      Brand New
      $39.99
      or Best Offer
      +$7.35 delivery
      Free returns
      Sponsored
      Top Rated Plus
    • Polo Ralph Lauren Boys Chino Shorts Navy Blue NWT Size 14 Youth Kids Preppy
      Find similar itemsSee all the items on eBay that match this style
      Polo Ralph Lauren Boys Chino Shorts Navy Blue NWT Size 14 Youth Kids Preppy
      Opens in a new window or tab
      Brand New
      $19.95
      Buy It Now
      +$4.84 delivery
      Sponsored
    • Ralph Lauren Boys Size 14 Bermuda Shorts Pink Plaid Preppy Easter Beach Golf
      Ralph Lauren Boys Size 14 Bermuda Shorts Pink Plaid Preppy Easter Beach Golf
      Opens in a new window or tab
      Pre-Owned
      $12.17
      Was: $13.9913% off
      Buy It Now
      +$7.01 delivery
      Sponsored
    • Hurley Nike Dri-Fit Mens Boys Sz 18 Gray Shorts Golf Casual Spring Summer Preppy
      Hurley Nike Dri-Fit Mens Boys Sz 18 Gray Shorts Golf Casual Spring Summer Preppy
      Opens in a new window or tab
      Pre-Owned
      $12.60
      Was: $14.0010% off
      Buy It Now
      +$6.55 delivery
      Sponsored
    • Vineyard Vines Boys Kids 14 Blue Uniform Dress Shep Ian Chino Adjustable Waist
      Vineyard Vines Boys Kids 14 Blue Uniform Dress Shep Ian Chino Adjustable Waist
      Opens in a new window or tab
      Pre-Owned
      $7.95
      Buy It Now
      +$5.95 delivery
      Sponsored
    • Polo Ralph Lauren Boys Prepster Shorts Sz 14 Chambray Blue
      Polo Ralph Lauren Boys Prepster Shorts Sz 14 Chambray Blue
      Opens in a new window or tab
      Pre-Owned
      $18.00
      or Best Offer
      +$9.91 delivery
      Sponsored
    • Vineyard Vines Boys 14 Plaid Shorts Blue Green Shep Ian Preppy 100% Cotton
      Vineyard Vines Boys 14 Plaid Shorts Blue Green Shep Ian Preppy 100% Cotton
      Opens in a new window or tab
      Pre-Owned
      $16.00
      or Best Offer
      +$4.84 delivery
      Sponsored
    • Vineyard Vines Boys BurgeeFlag Embroidery Club Shorts Ocean Splash 14 Blue NWT
      Vineyard Vines Boys BurgeeFlag Embroidery Club Shorts Ocean Splash 14 Blue NWT
      Opens in a new window or tab
      Brand New
      $20.00
      Buy It Now
      +$5.80 delivery
      Sponsored
    • Vineyard Vines Boys 'Whale' Embroidered Club Shorts Flag Blue $59.50 10,14,16
      Vineyard Vines Boys 'Whale' Embroidered Club Shorts Flag Blue $59.50 10,14,16
      Opens in a new window or tab
      Brand New
      $29.49
      Buy It Now
      Free delivery
      Free returns
      4+ watchers
      Sponsored
      Top Rated Plus
    • Vineyard Vines by Shep & Ian Boys Coral Chino Shorts Size 18
      Vineyard Vines by Shep & Ian Boys Coral Chino Shorts Size 18
      Opens in a new window or tab
      Pre-Owned
      $9.95
      or Best Offer
      +$5.85 delivery
      Sponsored
    • Crewcuts Boys Pink and Blue Striped Bermuda Seersucker Shorts Size 14
      Crewcuts Boys Pink and Blue Striped Bermuda Seersucker Shorts Size 14
      Opens in a new window or tab
      Pre-Owned
      $10.50
      Was: $15.0030% off
      or Best Offer
      +$5.80 delivery
      Free returns
      Sponsored
    • Brooks Brothers Shorts Youth Boy 18 Patchwork Plaid Cotton 28x10 Preppy Academia
      Brooks Brothers Shorts Youth Boy 18 Patchwork Plaid Cotton 28x10 Preppy Academia
      Opens in a new window or tab
      Pre-Owned
      $15.71
      Was: $26.1840% off
      or Best Offer
      +$5.26 delivery
      Sponsored
    • Vineyard Vines Shorts Boys Size 14 Beige Chino Casual Preppy Stretch Logo
      Vineyard Vines Shorts Boys Size 14 Beige Chino Casual Preppy Stretch Logo
      Opens in a new window or tab
      Pre-Owned
      $19.99
      or Best Offer
      +$5.95 delivery
      Free returns
      Sponsored
      Top Rated Plus
    • Vineyard Vines Seersucker Shorts Size 14 Boy Spring Summer Country Club Preppy
      Vineyard Vines Seersucker Shorts Size 14 Boy Spring Summer Country Club Preppy
      Opens in a new window or tab
      Pre-Owned
      $22.50
      or Best Offer
      +$8.71 delivery
      Sponsored
    • The Children's Place Boys Khaki Navy Cargo Pull On Adjustable Shorts Sz 14 Husky
      The Children's Place Boys Khaki Navy Cargo Pull On Adjustable Shorts Sz 14 Husky
      Opens in a new window or tab
      Pre-Owned
      $19.99
      or Best Offer
      +$10.00 delivery
      Sponsored
    • Polo Ralph Lauren Shorts Boys 14 Brown Tan Chino Preppy Casual Kids Youth
      Polo Ralph Lauren Shorts Boys 14 Brown Tan Chino Preppy Casual Kids Youth
      Opens in a new window or tab
      Pre-Owned
      $15.00
      or Best Offer
      Free delivery
      Sponsored
    • Vineyard Vines Boys Lobster Print Shorts Navy Blue & Red Size Size 14 Immaculate
      Vineyard Vines Boys Lobster Print Shorts Navy Blue & Red Size Size 14 Immaculate
      Opens in a new window or tab
      Pre-Owned
      $18.50
      or Best Offer
      +$7.35 delivery
      Sponsored
    • Vans Brown Multicolor Plaid Boys Shorts Size 18
      Vans Brown Multicolor Plaid Boys Shorts Size 18
      Opens in a new window or tab
      Pre-Owned
      $4.00
      0 bids · Time left3d 21h
      +$5.21 delivery
      Sponsored
    • Lot Of 2 Old Navy Boys School Uniform Pants, Khaki Flat Front Adjustable Size 14
      Lot Of 2 Old Navy Boys School Uniform Pants, Khaki Flat Front Adjustable Size 14
      Opens in a new window or tab
      Pre-Owned
      $12.00
      Buy It Now
      +$11.07 delivery
      Sponsored
    • EUC Vineyard Vines Boys Size 14 Classic Bermuda Shorts Blue Embroidered Lacrosse
      EUC Vineyard Vines Boys Size 14 Classic Bermuda Shorts Blue Embroidered Lacrosse
      Opens in a new window or tab
      Pre-Owned
      $14.95
      or Best Offer
      +$6.90 delivery in 2-4 days
      Sponsored
    • Vtg Polo Ralph Lauren Shorts Chino Khaki Boys Size 14 Beige Preppy Golf Pony
      Vtg Polo Ralph Lauren Shorts Chino Khaki Boys Size 14 Beige Preppy Golf Pony
      Opens in a new window or tab
      Pre-Owned
      $19.99
      or Best Offer
      +$10.10 delivery
      Sponsored
    • Nwt CLASS CLUB Dillard's MODERN FIT Boy's BLUE Stretch Twill CHINO Shorts Sz 14
      Nwt CLASS CLUB Dillard's MODERN FIT Boy's BLUE Stretch Twill CHINO Shorts Sz 14
      Opens in a new window or tab
      Brand New
      $10.80
      Was: $12.0010% off
      Buy It Now
      +$6.62 delivery
      Sponsored
    • Vineyard Vines Boys Size 14 Green Breaker Shorts Uniform School Preppy Nautical
      Vineyard Vines Boys Size 14 Green Breaker Shorts Uniform School Preppy Nautical
      Opens in a new window or tab
      Pre-Owned
      $10.00
      Buy It Now
      +$5.49 delivery
      Sponsored
    • Sz 18 Husky Boys Shorts, Khaki Chino 10" Inseam Flat Front New
      Sz 18 Husky Boys Shorts, Khaki Chino 10" Inseam Flat Front New
      Opens in a new window or tab
      New (Other)
      $10.99
      or Best Offer
      +$5.80 delivery
      Sponsored
    • Polo Ralph Lauren Boys Blue Chino Shorts Flat Front Sz 14 Preppy Coastal
      Polo Ralph Lauren Boys Blue Chino Shorts Flat Front Sz 14 Preppy Coastal
      Opens in a new window or tab
      Pre-Owned
      $9.80
      Was: $14.0030% off
      or Best Offer
      +$4.99 delivery
      Sponsored
    • POLO Ralph Lauren Cargo Boys Shorts Size 18 Khaki Tan Straight Leg Cotton Chino
      POLO Ralph Lauren Cargo Boys Shorts Size 18 Khaki Tan Straight Leg Cotton Chino
      Opens in a new window or tab
      Pre-Owned
      $15.00
      or Best Offer
      +$12.71 delivery
      Sponsored
    • Vineyard Vines Boys Summer Twill Breaker Blue Adjustable Waist Shorts Size 14
      Vineyard Vines Boys Summer Twill Breaker Blue Adjustable Waist Shorts Size 14
      Opens in a new window or tab
      Pre-Owned
      $16.00
      or Best Offer
      +$9.84 delivery
      Sponsored
    • Vineyard Vines Boys Cotton Summer Twill Club Shorts Antigua Green (14)  $59.50
      Vineyard Vines Boys Cotton Summer Twill Club Shorts Antigua Green (14) $59.50
      Opens in a new window or tab
      Brand New
      $29.50
      Buy It Now
      Free delivery
      Free returns
      Sponsored
      Top Rated Plus
    • Vineyard Vines Boys 'Whale' Embroidered Club Shorts Stone $59.50 Size 12 nd 14
      Vineyard Vines Boys 'Whale' Embroidered Club Shorts Stone $59.50 Size 12 nd 14
      Opens in a new window or tab
      Brand New
      $29.49
      Buy It Now
      Free delivery
      Free returns
      Sponsored
      Top Rated Plus
    • Kids Crown & Ivy Navy Flat Front Adjustable Shorts Size 14 Preppy Uniform Church
      Kids Crown & Ivy Navy Flat Front Adjustable Shorts Size 14 Preppy Uniform Church
      Opens in a new window or tab
      Pre-Owned
      $5.95
      or Best Offer
      +$5.80 delivery
      Sponsored
    • Wonder Nation Boys Sz 18 Shorts Blue Flat Front Chino Stretch Adjustable Preppy
      Wonder Nation Boys Sz 18 Shorts Blue Flat Front Chino Stretch Adjustable Preppy
      Opens in a new window or tab
      Pre-Owned
      $7.00
      or Best Offer
      +$7.00 delivery
      Free returns
      Extra 10% off with coupon
      Sponsored
      Top Rated Plus
    • Polo Ralph Lauren Denim Shorts Jorts  100% Cotton  10" Inseam Preppy Boys 14
      Polo Ralph Lauren Denim Shorts Jorts 100% Cotton 10" Inseam Preppy Boys 14
      Opens in a new window or tab
      Pre-Owned
      $19.98
      or Best Offer
      +$5.62 delivery
      Free returns
      Sponsored
      Top Rated Plus
    • Vineyard Vines Bermuda Shorts Boys Youth Size 14 Beige VERY GOOD
      Vineyard Vines Bermuda Shorts Boys Youth Size 14 Beige VERY GOOD
      Opens in a new window or tab
      Pre-Owned
      $9.99
      Buy It Now
      +$7.00 delivery
      Sponsored
    • Vineyard Vines Boys 'Whale' Embroidered Club Shorts Salmon
      Vineyard Vines Boys 'Whale' Embroidered Club Shorts Salmon
      Opens in a new window or tab
      Pre-Owned
      $24.95
      Buy It Now
      +$9.45 delivery
      Sponsored
    • Boys Vineyard Vines Club Khaki Golf Shorts 3H0141- Size 14
      Boys Vineyard Vines Club Khaki Golf Shorts 3H0141- Size 14
      Opens in a new window or tab
      Pre-Owned
      $9.97
      or Best Offer
      +$4.71 delivery
      Sponsored
    • Vineyard Vines Coral Bermuda Boys Kids Shorts Preppy 14 323 Preppy
      Vineyard Vines Coral Bermuda Boys Kids Shorts Preppy 14 323 Preppy
      Opens in a new window or tab
      Pre-Owned
      $12.95
      Buy It Now
      +$6.00 delivery
      Sponsored
    • Vineyard Vines Kids Boys Cotton Summer Twill Club Shorts Starboard Green  $59.50
      Vineyard Vines Kids Boys Cotton Summer Twill Club Shorts Starboard Green $59.50
      Opens in a new window or tab
      Brand New
      $34.49
      Buy It Now
      Free delivery
      Free returns
      Sponsored
      Top Rated Plus
    • Pantagonia Boys Fitz Stripe Board Shorts Swim Trunks Size 14 Beach Preppy Active
      Pantagonia Boys Fitz Stripe Board Shorts Swim Trunks Size 14 Beach Preppy Active
      Opens in a new window or tab
      Pre-Owned
      $18.00
      Buy It Now
      +$4.71 delivery
      Sponsored
    • Tailor Vintage Boys Size 14 Pink Bermuda Shorts
      Tailor Vintage Boys Size 14 Pink Bermuda Shorts
      Opens in a new window or tab
      Pre-Owned
      $9.25
      or Best Offer
      +$6.99 delivery
      Sponsored
    • NWT There Abouts Boys Size 14 Lexington Light Green Chino Shorts MSRP $32
      NWT There Abouts Boys Size 14 Lexington Light Green Chino Shorts MSRP $32
      Opens in a new window or tab
      Brand New
      $19.99
      Buy It Now
      +$5.71 delivery
      Extra 10% off with coupon
      Sponsored
    • Polo Ralph Lauren Pink Preppy Bermuda Long Shorts boys 18
      Polo Ralph Lauren Pink Preppy Bermuda Long Shorts boys 18
      Opens in a new window or tab
      Pre-Owned
      $22.00
      or Best Offer
      +$8.90 delivery
      Sponsored
    • Vineyard Vines Breaker Shorts Blue Twill Cotton Casual Stretch Youth Boys 14
      Vineyard Vines Breaker Shorts Blue Twill Cotton Casual Stretch Youth Boys 14
      Opens in a new window or tab
      Brand New
      $49.99
      Buy It Now
      +$6.99 delivery
      Sponsored
    • Vtg Polo Ralph Lauren Shorts Chino Khaki Boys Size 14 Navy Blue Preppy Golf Pony
      Vtg Polo Ralph Lauren Shorts Chino Khaki Boys Size 14 Navy Blue Preppy Golf Pony
      Opens in a new window or tab
      Pre-Owned
      $19.99
      or Best Offer
      +$10.10 delivery
      Sponsored
    • Lot Of 2 Old Navy Boys School Uniform Pants, Khaki Flat Front Adjustable Size 14
      Lot Of 2 Old Navy Boys School Uniform Pants, Khaki Flat Front Adjustable Size 14
      Opens in a new window or tab
      Pre-Owned
      $12.00
      Buy It Now
      +$11.07 delivery
      Sponsored
    • Vineyard Vines Shorts Boys 14 Blue Embroidered Lacrosse Lax Casual Preppy Cotton
      Vineyard Vines Shorts Boys 14 Blue Embroidered Lacrosse Lax Casual Preppy Cotton
      Opens in a new window or tab
      Pre-Owned
      $8.00
      Was: $10.0020% off
      or Best Offer
      +$4.80 delivery
      Sponsored
    • Vineyard Vines Shorts Boys Size 14 Beige Chino Casual Preppy Stretch Logo
      Vineyard Vines Shorts Boys Size 14 Beige Chino Casual Preppy Stretch Logo
      Opens in a new window or tab
      Pre-Owned
      $15.00
      Buy It Now
      +$5.62 delivery
      Sponsored
    • Abercrombie & Fitch Gingham Plaid Shorts Boys Size 14 Blue White Bermuda Preppy
      Abercrombie & Fitch Gingham Plaid Shorts Boys Size 14 Blue White Bermuda Preppy
      Opens in a new window or tab
      Pre-Owned
      $24.99
      or Best Offer
      Free delivery
      Free returns
      Sponsored
    • Lot of Two Pair Boys Preppy Shorts Sz 14 Tucker & Tate Tony Hawk
      Lot of Two Pair Boys Preppy Shorts Sz 14 Tucker & Tate Tony Hawk
      Opens in a new window or tab
      Pre-Owned
      $14.00
      or Best Offer
      +$10.84 delivery
      Sponsored
    • URBAN PIPELINE youth size 14 plaid bermuda shorts walking tan preppy beige surf
      URBAN PIPELINE youth size 14 plaid bermuda shorts walking tan preppy beige surf
      Opens in a new window or tab
      Pre-Owned
      $11.99
      Buy It Now
      Free delivery
      Sponsored
    • Buffalo David Bitton Boys Denim Parker Jean Shorts Fray Hem Distressed SZ 14
      Buffalo David Bitton Boys Denim Parker Jean Shorts Fray Hem Distressed SZ 14
      Opens in a new window or tab
      Pre-Owned
      $23.00
      or Best Offer
      +$7.50 delivery
      Sponsored
    • Vineyard Vines Seersucker Boat Embroidered Shorts Boys 14 Adjustable Waist
      Vineyard Vines Seersucker Boat Embroidered Shorts Boys 14 Adjustable Waist
      Opens in a new window or tab
      Pre-Owned
      $20.00
      or Best Offer
      +$6.55 delivery
      Sponsored
    • Boys Ralph Lauren Classic Polo Chino Shorts 18 29 in waist White Navy Ponys Golf
      Boys Ralph Lauren Classic Polo Chino Shorts 18 29 in waist White Navy Ponys Golf
      Opens in a new window or tab
      Pre-Owned
      $22.07
      Was: $23.998% off
      or Best Offer
      +$5.25 delivery
      Sponsored
    • Vineyard Vines Shep & Ian Boys 14 Chino Shorts Light Blue Preppy Shorts Golf
      Vineyard Vines Shep & Ian Boys 14 Chino Shorts Light Blue Preppy Shorts Golf
      Opens in a new window or tab
      Pre-Owned
      $22.00
      or Best Offer
      Free delivery
      Sponsored
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