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466 results

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    • 90sRemove filter
    • PreppyRemove filter
    • Size: 20Remove filter
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    • Vintage Y2K Levis Carpenter Shorts Boys 14 Baggy Loose Denim Casual Retro Skater
      Vintage Y2K Levis Carpenter Shorts Boys 14 Baggy Loose Denim Casual Retro Skater
      Opens in a new window or tab
      Pre-Owned
      $19.78
      or Best Offer
      +$7.95 delivery in 2-4 days
      Free returns
      Sponsored
      Top Rated Plus
    • Polo Ralph Lauren Shorts Set of 2 Boys Size 20 Green Red Classic Preppy Casual
      Polo Ralph Lauren Shorts Set of 2 Boys Size 20 Green Red Classic Preppy Casual
      Opens in a new window or tab
      Pre-Owned
      $32.95
      or Best Offer
      +$7.25 delivery
      Sponsored
    • Vintage Levi's Shorts Youth 14 Blue Distressed Carpenter Loose Fit Baggy Y2K 90s
      Vintage Levi's Shorts Youth 14 Blue Distressed Carpenter Loose Fit Baggy Y2K 90s
      Opens in a new window or tab
      Pre-Owned
      $35.99
      or Best Offer
      +$8.85 delivery in 2-4 days
      Sponsored
    • Polo Ralph Lauren Flat Front Casual Shorts Boys Size 14
      Polo Ralph Lauren Flat Front Casual Shorts Boys Size 14
      Opens in a new window or tab
      Pre-Owned
      $20.00
      Was: $25.0020% off
      or Best Offer
      +$7.25 delivery
      Sponsored
    • VTG Gap Boys Blue Jean Work Wear Double Knee Long Shorts Y2K Jorts 27x12 Sz14
      VTG Gap Boys Blue Jean Work Wear Double Knee Long Shorts Y2K Jorts 27x12 Sz14
      Opens in a new window or tab
      Pre-Owned
      $17.88
      or Best Offer
      +$7.88 delivery
      Sponsored
    • Polo Ralph Lauren Shorts Youth Boys 14 Khaki Bear All Over Embroidered Logo
      Polo Ralph Lauren Shorts Youth Boys 14 Khaki Bear All Over Embroidered Logo
      Opens in a new window or tab
      Pre-Owned
      $17.95
      Was: $19.9510% off
      Buy It Now
      +$9.45 delivery
      Free returns
      Sponsored
      Top Rated Plus
    • Vintage Y2K Flamehead Embroidered Skate Denim Shorts Youth 14 Black
      Vintage Y2K Flamehead Embroidered Skate Denim Shorts Youth 14 Black
      Opens in a new window or tab
      Pre-Owned
      $99.99
      or Best Offer
      +$8.71 delivery
      Sponsored
    • Vineyard Vines Size 14 Boys Performance Shorts! NWT!
      Vineyard Vines Size 14 Boys Performance Shorts! NWT!
      Opens in a new window or tab
      Brand New
      $20.00
      or Best Offer
      +$4.84 delivery
      Sponsored
    • Picked For You

      Top selling items from trusted sellers | 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
          $29.50
          coachjustyou (2,245) 100%
        • Vineyard Vines Club Shorts Boys Great Quality Shorts - Multiple Sizes/Colors!
          Vineyard Vines Club Shorts Boys Great Quality Shorts - Multiple Sizes/Colors!
          Opens in a new window or tab
          $24.99
          vinchin1475 (1,021) 100%
        • Short Bermuda Chino Pump Baggy Fabric Capri Shorts Child Boy 22673
          Short Bermuda Chino Pump Baggy Fabric Capri Shorts Child Boy 22673
          Opens in a new window or tab
          $22.17
          pbezler (55,978) 100%
        • Pure Stuff Shorts Boys 14 Navy Golf Preppy Church Pockets Cargo Uniform Chino
          Pure Stuff Shorts Boys 14 Navy Golf Preppy Church Pockets Cargo Uniform Chino
          Opens in a new window or tab
          $15.99
          connectedthreads (1,984) 99.6%
    • NWT Polo Ralph Lauren shorts boys size 20 camouflage drawstring button Zip
      NWT Polo Ralph Lauren shorts boys size 20 camouflage drawstring button Zip
      Opens in a new window or tab
      Brand New
      $29.88
      or Best Offer
      +$6.50 delivery
      Free returns
      Sponsored
    • Vineyard Vines Shorts Youth Boys Size 14 Khaki Shorts (N3)
      Vineyard Vines Shorts Youth Boys Size 14 Khaki Shorts (N3)
      Opens in a new window or tab
      Pre-Owned
      $11.34
      or Best Offer
      +$5.62 delivery
      Extra 15% off with coupon
      Sponsored
    • Vtg Y2K JNCO JEANS Camo Cargo Shorts Dragon Logo Rare Baggy Youth Sz 14 (27x11)
      Vtg Y2K JNCO JEANS Camo Cargo Shorts Dragon Logo Rare Baggy Youth Sz 14 (27x11)
      Opens in a new window or tab
      Pre-Owned
      $79.95
      Buy It Now
      Free delivery
      Sponsored
    • VTG Blue Denim Jorts Youth 14 Baggy Skater Y2K Boys
      VTG Blue Denim Jorts Youth 14 Baggy Skater Y2K Boys
      Opens in a new window or tab
      Pre-Owned
      $24.99
      or Best Offer
      +$6.98 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
    • J. Crew Crewcuts Boys Shorts Size 14
      J. Crew Crewcuts Boys Shorts Size 14
      Opens in a new window or tab
      Pre-Owned
      $10.00
      or Best Offer
      +$4.84 delivery
      Sponsored
    • Vineyard Vines by Shep & Ian Flat Front Casual Shorts Boys Size 14 (10" Inseam)
      Vineyard Vines by Shep & Ian Flat Front Casual Shorts Boys Size 14 (10" Inseam)
      Opens in a new window or tab
      Pre-Owned
      $17.60
      Was: $22.0020% off
      or Best Offer
      +$7.25 delivery
      Sponsored
    • Vineyard Vines by Shep & Ian Flat Front Casual Shorts Boys Size 14
      Vineyard Vines by Shep & Ian Flat Front Casual Shorts Boys Size 14
      Opens in a new window or tab
      Pre-Owned
      $17.60
      Was: $22.0020% off
      or Best Offer
      +$7.25 delivery
      Sponsored
    • Vineyard Vines Shorts Boys size 14 Seer Sucker Stripe Chino Preppy Yacht Summer
      Vineyard Vines Shorts Boys size 14 Seer Sucker Stripe Chino Preppy Yacht Summer
      Opens in a new window or tab
      Pre-Owned
      $19.98
      or Best Offer
      +$5.99 delivery in 2-3 days
      Free returns
      Extra 10% off with coupon
      Sponsored
      Top Rated Plus
    • Polo Ralph Lauren Shorts Boys 20 The Sullivan Slim Youth Denim Cuffed Stretch
      Polo Ralph Lauren Shorts Boys 20 The Sullivan Slim Youth Denim Cuffed Stretch
      Opens in a new window or tab
      Brand New
      $29.99
      or Best Offer
      +$6.99 delivery
      Free returns
      Sponsored
      Top Rated Plus
    • Polo Ralph Lauren Shorts Boy 14 Youth Tan Chino Khaki School Preppy Beach
      Polo Ralph Lauren Shorts Boy 14 Youth Tan Chino Khaki School Preppy Beach
      Opens in a new window or tab
      Pre-Owned
      $14.42
      Was: $16.9615% off
      or Best Offer
      +$5.95 delivery in 2-4 days
      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
      Sponsored
    • LOT OF 4 Boys Shorts-Nike, Chaps, Reebok, Old Navy - Size 14/16
      LOT OF 4 Boys Shorts-Nike, Chaps, Reebok, Old Navy - Size 14/16
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      Pre-Owned
      $20.00
      or Best Offer
      +$14.00 delivery
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    • Gap Kids Shorts Boys Size 14 Gray Chino Stretch Uniform Dressy, NEW
      Gap Kids Shorts Boys Size 14 Gray Chino Stretch Uniform Dressy, NEW
      Opens in a new window or tab
      Brand New
      $15.99
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      +$6.25 delivery
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    • Vtg Tommy Hilfiger Chino Shorts Youth Unisex Sz 14 Pleated Relaxed Cotton Green
      Vtg Tommy Hilfiger Chino Shorts Youth Unisex Sz 14 Pleated Relaxed Cotton Green
      Opens in a new window or tab
      Pre-Owned
      $14.99
      or Best Offer
      +$7.96 delivery
      Free returns
      Sponsored
    • janie and jack boys size 14 pink polo and pink/blue plaid shorts
      janie and jack boys size 14 pink polo and pink/blue plaid shorts
      Opens in a new window or tab
      Pre-Owned
      $19.00
      0 bids · Time left6d 2h
      $24.70
      Buy It Now
      +$10.00 delivery
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    • Vintage Y2K Pelle Pelle Jean Shorts Youth Boys Size 14 Embroidered Jorts 90’s
      Vintage Y2K Pelle Pelle Jean Shorts Youth Boys Size 14 Embroidered Jorts 90’s
      Opens in a new window or tab
      Pre-Owned
      $21.39
      Was: $25.1615% off
      or Best Offer
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    • Vintage Fubu Cargo Shorts Carpenter Baggy Skaters Y2K 90s Boys size 14
      Vintage Fubu Cargo Shorts Carpenter Baggy Skaters Y2K 90s Boys size 14
      Opens in a new window or tab
      Pre-Owned
      $22.00
      or Best Offer
      +$6.22 delivery
      Sponsored
    • Vineyard Vines Salmon Boys Shorts Size 14 EUC
      Vineyard Vines Salmon Boys Shorts Size 14 EUC
      Opens in a new window or tab
      Pre-Owned
      $14.25
      or Best Offer
      +$8.71 delivery
      Sponsored
    • Polo Ralph Lauren Khaki Shorts Youth Size 14 Boys NWT Beige Chino New
      Polo Ralph Lauren Khaki Shorts Youth Size 14 Boys NWT Beige Chino New
      Opens in a new window or tab
      Brand New
      $24.99
      or Best Offer
      +$5.00 delivery
      Sponsored
    • Polo Ralph Lauren Flat Front Casual Shorts Boys Size 20
      Polo Ralph Lauren Flat Front Casual Shorts Boys Size 20
      Opens in a new window or tab
      Pre-Owned
      $20.00
      Was: $25.0020% off
      or Best Offer
      +$7.25 delivery
      Sponsored
    • Polo Ralph Lauren Shorts Boys 14 Brown Khaki Cargo Baggy Loose Skater Youth PRL
      Polo Ralph Lauren Shorts Boys 14 Brown Khaki Cargo Baggy Loose Skater Youth PRL
      Opens in a new window or tab
      Pre-Owned
      $16.24
      Was: $24.9935% off
      or Best Offer
      +$6.99 delivery
      Free returns
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      Top Rated Plus
    • POLO RALPH LAUREN Striped Pony All Over Chino Shorts Mens 14 White
      POLO RALPH LAUREN Striped Pony All Over Chino Shorts Mens 14 White
      Opens in a new window or tab
      Pre-Owned
      $8.53
      or Best Offer
      +$7.10 delivery
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    • Ralph Lauren Polo Shorts Boys 14 Green Camo Cargo Surplus Army Military Y2K VTG
      Ralph Lauren Polo Shorts Boys 14 Green Camo Cargo Surplus Army Military Y2K VTG
      Opens in a new window or tab
      Pre-Owned
      $19.99
      Was: $24.9920% off
      or Best Offer
      +$5.99 delivery
      Free returns
      Sponsored
      Top Rated Plus
    • Vintage Coogi Jean Shorts Boys JNCO Style Baggy Y2K 90s Skater Sz 14 Embroidered
      Vintage Coogi Jean Shorts Boys JNCO Style Baggy Y2K 90s Skater Sz 14 Embroidered
      Opens in a new window or tab
      Pre-Owned
      $33.75
      Was: $37.5010% off
      or Best Offer
      +$5.99 delivery
      Free returns
      Sponsored
      Top Rated Plus
    • Vintage Fubu Cargo Shorts Carpenter Baggy Skaters Y2K 90s Boys size 14
      Vintage Fubu Cargo Shorts Carpenter Baggy Skaters Y2K 90s Boys size 14
      Opens in a new window or tab
      Pre-Owned
      $22.00
      or Best Offer
      +$6.22 delivery
      Sponsored
    • Polo Ralph Lauren Spring II Beige Shorts w/Belt - NEW w/TAGS - Size 20 Boys
      Polo Ralph Lauren Spring II Beige Shorts w/Belt - NEW w/TAGS - Size 20 Boys
      Opens in a new window or tab
      Brand New
      $32.00
      or Best Offer
      +$6.84 delivery
      Sponsored
    • Polo Ralph Lauren Chambray Shorts Boy's Size 20 Light Blue 10" Inseam Preppy
      Polo Ralph Lauren Chambray Shorts Boy's Size 20 Light Blue 10" Inseam Preppy
      Opens in a new window or tab
      Pre-Owned
      $15.77
      or Best Offer
      +$7.35 delivery
      Free returns
      Sponsored
      Top Rated Plus
    • Vintage 1990s Polo Ralph Lauren Shorts Boys Sz 14 Cotten Bermuda Shorts Striped
      Vintage 1990s Polo Ralph Lauren Shorts Boys Sz 14 Cotten Bermuda Shorts Striped
      Opens in a new window or tab
      Pre-Owned
      $10.49
      Was: $14.9930% off
      or Best Offer
      +$5.80 delivery
      Sponsored
    • VTG Arizona Boys Deadstock Green Canvas Carpenter Long Shorts Y2K 28x12 Sz14
      VTG Arizona Boys Deadstock Green Canvas Carpenter Long Shorts Y2K 28x12 Sz14
      Opens in a new window or tab
      Pre-Owned
      $14.88
      or Best Offer
      +$8.78 delivery
      Sponsored
    • JNCO Jean Shorts BMX Bike City Graphic Boys Sz 20 Vtg 90s Y2K Baggy Wide Mens 28
      JNCO Jean Shorts BMX Bike City Graphic Boys Sz 20 Vtg 90s Y2K Baggy Wide Mens 28
      Opens in a new window or tab
      Pre-Owned
      $125.00
      Buy It Now
      +$8.95 delivery
      12 watchers
      Sponsored
    • Vintage Southpole Shorts Youth 14 Blue Distressed Loose Fit Baggy Y2K 90s HipHop
      Vintage Southpole Shorts Youth 14 Blue Distressed Loose Fit Baggy Y2K 90s HipHop
      Opens in a new window or tab
      Pre-Owned
      $35.99
      or Best Offer
      +$8.85 delivery in 2-4 days
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    • 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
    • Carhartt Canvas Cargo Work Shorts Brown BS8309 Boys/Kids Size 14
      Carhartt Canvas Cargo Work Shorts Brown BS8309 Boys/Kids Size 14
      Opens in a new window or tab
      Pre-Owned
      $12.60
      Was: $14.0010% off
      or Best Offer
      +$9.45 delivery
      Sponsored
    • Polo Ralph Lauren Boys' Paint Splatter Sullivan Slim Denim Shorts Size 14 NWT
      Polo Ralph Lauren Boys' Paint Splatter Sullivan Slim Denim Shorts Size 14 NWT
      Opens in a new window or tab
      Brand New
      $23.99
      Was: $29.9920% off
      or Best Offer
      +$7.25 delivery
      Last one
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    • Boys Polo Ralph Lauren Size 20 Khaki Shorts
      Boys Polo Ralph Lauren Size 20 Khaki Shorts
      Opens in a new window or tab
      Pre-Owned
      $19.99
      0 bids · Time left6d 10h
      or Best Offer
      +$12.71 delivery
      Sponsored
    • Boys Polo Ralph Lauren Khaki Shorts Size 20
      Boys Polo Ralph Lauren Khaki Shorts Size 20
      Opens in a new window or tab
      Pre-Owned
      $19.99
      0 bids · Time left6d 10h
      or Best Offer
      +$12.71 delivery
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    • Polo Ralph Lauren Bear Ralph's Tigers Drawstring Shorts Preppy Boys Youth Sz 14
      Polo Ralph Lauren Bear Ralph's Tigers Drawstring Shorts Preppy Boys Youth Sz 14
      Opens in a new window or tab
      Pre-Owned
      $18.00
      or Best Offer
      +$5.25 delivery in 2-4 days
      Free returns
      Sponsored
      Top Rated Plus
    • VTG Y2K Paco Sz 16 Skater Shorts Wide Baggy Jnco Jorts Denim Black
      VTG Y2K Paco Sz 16 Skater Shorts Wide Baggy Jnco Jorts Denim Black
      Opens in a new window or tab
      Pre-Owned
      $29.95
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      +$7.95 delivery
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    • Polo Ralph Lauren Yellow Chino Shorts Boys Size 20 NEW Preppy Cotton
      Polo Ralph Lauren Yellow Chino Shorts Boys Size 20 NEW Preppy Cotton
      Opens in a new window or tab
      Brand New
      $17.00
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      +$7.35 delivery
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    • NWOT Crewcuts Boy’s Gramercy Seersucker 9” Shorts 14 Blue Stripe $50 Adjustable
      NWOT Crewcuts Boy’s Gramercy Seersucker 9” Shorts 14 Blue Stripe $50 Adjustable
      Opens in a new window or tab
      New (Other)
      $19.99
      Buy It Now
      +$4.84 delivery
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    • 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
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      +$5.95 delivery
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    • Under Armour Golf Shorts Boys Size 14 Chino Inseam Gray Heatgear
      Under Armour Golf Shorts Boys Size 14 Chino Inseam Gray Heatgear
      Opens in a new window or tab
      Pre-Owned
      $9.89
      0 bids · Time left2d 12h
      +$6.55 delivery
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    • Tommy Hilfiger Boys Size 20 Slim Navy Blue Shorts Uniform Bermuda NWT
      Tommy Hilfiger Boys Size 20 Slim Navy Blue Shorts Uniform Bermuda NWT
      Opens in a new window or tab
      Brand New
      $15.00
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      +$7.35 delivery
      10% off 2+ with coupon
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    • Polo Ralph Lauren The Sullivan Slim Denim Shorts Paint Splatter Boys Size 20 NWT
      Polo Ralph Lauren The Sullivan Slim Denim Shorts Paint Splatter Boys Size 20 NWT
      Opens in a new window or tab
      Brand New
      $29.95
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      Free delivery
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    • Children's Place Shorts Cargo Khaki Elastic Adjustable Boy Sizes 12, 14, or 18
      Children's Place Shorts Cargo Khaki Elastic Adjustable Boy Sizes 12, 14, or 18
      Opens in a new window or tab
      Pre-Owned
      $5.00
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      +$6.55 delivery
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    • UA Matchplay Shorts Boys Size 14 Barley Tan Neutral Preppy Golf Classic
      UA Matchplay Shorts Boys Size 14 Barley Tan Neutral Preppy Golf Classic
      Opens in a new window or tab
      Pre-Owned
      $19.00
      or Best Offer
      +$6.40 delivery
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    • J.Crew Crewcuts Boys Khaki Cotton Chino Shorts Adjustable Waist Boys Size 14
      J.Crew Crewcuts Boys Khaki Cotton Chino Shorts Adjustable Waist Boys Size 14
      Opens in a new window or tab
      Pre-Owned
      $9.00
      0 bids · Time left12h 21m
      or Best Offer
      +$4.84 delivery
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    • Tommy Hilfiger Youth Cargo Shorts Stretch Boys Sz 14 Pink Preppy New
      Tommy Hilfiger Youth Cargo Shorts Stretch Boys Sz 14 Pink Preppy New
      Opens in a new window or tab
      Brand New
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      +$8.19 delivery
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    • 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
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    • Polo Ralph Lauren Chino Cargo Shorts Youth 14 Khaki/Beige Classic Preppy
      Polo Ralph Lauren Chino Cargo Shorts Youth 14 Khaki/Beige Classic Preppy
      Opens in a new window or tab
      Pre-Owned
      $12.00
      or Best Offer
      +$5.91 delivery in 2-4 days
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    • Under Armour Golf Shorts Boys Size 14 Chino Inseam Gray Heatgear
      Under Armour Golf Shorts Boys Size 14 Chino Inseam Gray Heatgear
      Opens in a new window or tab
      Pre-Owned
      $11.15
      Buy It Now
      +$5.00 delivery
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    • Boy's Levi's Shorts SLIM Premium Stretch Denim Blue Tag 20 Reg measured Size 30
      Boy's Levi's Shorts SLIM Premium Stretch Denim Blue Tag 20 Reg measured Size 30
      Opens in a new window or tab
      Brand New
      $20.17
      Was: $21.928% off
      Buy It Now
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    • Polo Ralph Lauren Boy's Chino Shorts Size 14 Tan Preppy 9" Inseam
      Polo Ralph Lauren Boy's Chino Shorts Size 14 Tan Preppy 9" Inseam
      Opens in a new window or tab
      Pre-Owned
      $9.99
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      +$7.02 delivery
      Free returns
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    • Polo Ralph Lauren Boy's BLUE Khaki Shorts Size 20 Preppy Casual NEW
      Polo Ralph Lauren Boy's BLUE Khaki Shorts Size 20 Preppy Casual NEW
      Opens in a new window or tab
      Brand New
      $22.00
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      +$6.84 delivery
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    • Janie and Jack Blue Pull On Linen Shorts Boys Size 14 NWT
      Janie and Jack Blue Pull On Linen Shorts Boys Size 14 NWT
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      Brand New
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      +$6.20 delivery
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