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    • PreppyRemove filter
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    • Properly Tied Youth Small 8 Boys Shorts Grey Elastic Waist Preppy
      Properly Tied Youth Small 8 Boys Shorts Grey Elastic Waist Preppy
      Opens in a new window or tab
      Brand New
      $20.26
      or Best Offer
      +$8.71 delivery
      Sponsored
    • 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
    • Tommy Hilfiger Boy's Drawstring Waist Blue White Seersucker Shorts Size Medium
      Tommy Hilfiger Boy's Drawstring Waist Blue White Seersucker Shorts Size Medium
      Opens in a new window or tab
      Pre-Owned
      $12.99
      or Best Offer
      +$5.80 delivery
      Free returns
      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
      +$6.99 delivery
      Sponsored
    • Vineyard Vines by Shep & Ian Flat Front Casual Shorts Boys Size 14 TWO PAIR PACK
      Find similar itemsSee all the items on eBay that match this style
      Vineyard Vines by Shep & Ian Flat Front Casual Shorts Boys Size 14 TWO PAIR PACK
      Opens in a new window or tab
      Pre-Owned
      $25.00
      Buy It Now
      +$9.39 delivery
      Sponsored
    • Nike Youth Boys Golf Shorts Sz M Black Stretch Chino Performance 10” Preppy
      Nike Youth Boys Golf Shorts Sz M Black Stretch Chino Performance 10” Preppy
      Opens in a new window or tab
      Pre-Owned
      $9.99
      or Best Offer
      +$6.50 delivery
      Free returns
      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 Shorts Men's XS Youth Large Peeking Polo Bear Double Knit
      Polo Ralph Lauren Shorts Men's XS Youth Large Peeking Polo Bear Double Knit
      Opens in a new window or tab
      Pre-Owned
      $28.99
      Buy It Now
      Free delivery
      Free returns
      Sponsored
      Top Rated Plus
    • Picked For You

      Top selling items from trusted sellers | Sponsored
        • 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 (1,025) 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
          $22.84
          connectedthreads (2,020) 99.6%
        • 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 (2,246) 100%
        • 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
          $29.49
          coachjustyou (2,246) 100%
        • 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
          $34.49
          coachjustyou (2,246) 100%
    • 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
    • Polo Ralph Lauren Shorts  Boys 20  Blue & White Striped NEW
      Polo Ralph Lauren Shorts Boys 20 Blue & White Striped NEW
      Opens in a new window or tab
      Brand New
      $15.00
      or Best Offer
      +$4.84 delivery
      Sponsored
    • Janie & Jack Boys’ Linen Blend Shorts Blue Chambray Size 14 Stretch Waist
      Janie & Jack Boys’ Linen Blend Shorts Blue Chambray Size 14 Stretch Waist
      Opens in a new window or tab
      Pre-Owned
      $17.00
      or Best Offer
      +$4.41 delivery in 2-4 days
      Sponsored
    • Polo Ralph Lauren Boys 20 Shorts Navy Blue Cotton Spring II Youth NEW
      Polo Ralph Lauren Boys 20 Shorts Navy Blue Cotton Spring II Youth NEW
      Opens in a new window or tab
      Brand New
      $19.59
      Was: $27.9930% off
      Buy It Now
      +$5.80 delivery
      Free returns
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    • Boys Elastic Waist Drawstring Cotton Blend Army Camouflage Kids Cargo Shorts
      Boys Elastic Waist Drawstring Cotton Blend Army Camouflage Kids Cargo Shorts
      Opens in a new window or tab
      Brand New
      $26.74
      Buy It Now
      Free delivery in 2-4 days
      Free returns
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    • 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
      $15.00
      or Best Offer
      +$5.80 delivery
      Free returns
      Sponsored
    • Polo Ralph Lauren Pants Youth Medium Athletic Gym Sweats Jogger Gray Preppy Boys
      Polo Ralph Lauren Pants Youth Medium Athletic Gym Sweats Jogger Gray Preppy Boys
      Opens in a new window or tab
      Pre-Owned
      $24.99
      or Best Offer
      +$8.99 delivery
      Free returns
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      Top Rated Plus
    • 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
    • Vineyard Vines Size 14 Blue Boys Performance Shorts! NWT! Great Buy!
      Vineyard Vines Size 14 Blue Boys Performance Shorts! NWT! Great Buy!
      Opens in a new window or tab
      Brand New
      $22.99
      or Best Offer
      +$8.84 delivery
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    • 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
      $19.95
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      +$9.45 delivery
      Free returns
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      Top Rated Plus
    • Boden Jersey Baggies Shorts Boys 14 Striped Blue White 100% Cotton Nautical
      Boden Jersey Baggies Shorts Boys 14 Striped Blue White 100% Cotton Nautical
      Opens in a new window or tab
      Pre-Owned
      $18.00
      Was: $20.0010% off
      or Best Offer
      +$5.99 delivery
      Free returns
      Extra 10% off with coupon
      Sponsored
      Top Rated Plus
    • Gap Boy's Elastic Waistband Front & Back Pockets Stretch Soft Twill Shorts
      Gap Boy's Elastic Waistband Front & Back Pockets Stretch Soft Twill Shorts
      Opens in a new window or tab
      Brand New
      $14.99
      List price: $30.9952% off
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      Free delivery in 2-4 days
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    • NWT POLO RALPH LAUREN Sullivan Slim Fit Distressed Denim Jean Shorts Boys 20
      NWT POLO RALPH LAUREN Sullivan Slim Fit Distressed Denim Jean Shorts Boys 20
      Opens in a new window or tab
      Brand New
      $26.10
      or Best Offer
      +$6.95 delivery
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    • Boys Plaid Shorts 4-5 Gap Golf Pleated Check Colorful Purple Green y2k Vtg XS
      Boys Plaid Shorts 4-5 Gap Golf Pleated Check Colorful Purple Green y2k Vtg XS
      Opens in a new window or tab
      Pre-Owned
      $9.75
      or Best Offer
      +$5.80 delivery
      Sponsored
    • Polo Ralph Lauren Shorts Boys Size 14 Khaki Cotton Cargo Drawstring Youth
      Polo Ralph Lauren Shorts Boys Size 14 Khaki Cotton Cargo Drawstring Youth
      Opens in a new window or tab
      Pre-Owned
      $11.49
      or Best Offer
      +$7.35 delivery
      Free returns
      Extra 15% off with coupon
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      Top Rated Plus
    • Two Pack Lot GAP Boys Hybrid Khaki & Black Cargo Shorts Quick Dry Stretch NWT
      Two Pack Lot GAP Boys Hybrid Khaki & Black Cargo Shorts Quick Dry Stretch NWT
      Opens in a new window or tab
      Brand New
      $28.60
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      Save up to 9% when you buy more
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    • Eddie Bauer Big Boy's 2-pack Youth Hybrid Quick Dry Mesh Lined Active Shorts
      Eddie Bauer Big Boy's 2-pack Youth Hybrid Quick Dry Mesh Lined Active Shorts
      Opens in a new window or tab
      Brand New
      $24.99
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    • Polo Ralph Lauren Shorts Boys 20 Prepster Patchwork Plaid Madras Preppy
      Polo Ralph Lauren Shorts Boys 20 Prepster Patchwork Plaid Madras Preppy
      Opens in a new window or tab
      Pre-Owned
      $19.99
      or Best Offer
      +$6.99 delivery
      Free returns
      Sponsored
      Top Rated Plus
    • 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
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    • Vineyard Vines Performance Boy’s Shorts Chino Size 14 Adjustable Waist 9” Inseam
      Vineyard Vines Performance Boy’s Shorts Chino Size 14 Adjustable Waist 9” Inseam
      Opens in a new window or tab
      Pre-Owned
      $14.00
      or Best Offer
      +$12.71 delivery
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    • Chubbies Shorts Boys Medium Burnt Orange Brown Cotton Regular Fit 3.5" *
      Chubbies Shorts Boys Medium Burnt Orange Brown Cotton Regular Fit 3.5" *
      Opens in a new window or tab
      Pre-Owned
      $24.99
      or Best Offer
      +$7.99 delivery
      Free returns
      30% off 2+ with coupon
      Sponsored
      Top Rated Plus
    • 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
      +$6.99 delivery
      Sponsored
    • Vineyard Vines by Shep & Ian Lacrosse Print Casual Shorts Boys Size 14
      Vineyard Vines by Shep & Ian Lacrosse Print Casual Shorts Boys Size 14
      Opens in a new window or tab
      Pre-Owned
      $17.60
      Was: $22.0020% off
      or Best Offer
      +$6.99 delivery
      Sponsored
    • Rip Curl Shorts Boys 23 Gray Chino Outdoors Casual Comfort Preppy
      Rip Curl Shorts Boys 23 Gray Chino Outdoors Casual Comfort Preppy
      Opens in a new window or tab
      Pre-Owned
      $19.99
      or Best Offer
      +$6.99 delivery in 2-4 days
      Free returns
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      Top Rated Plus
    • Ralph Lauren Polo Shorts Boys 20 NEW Patchwork Plaid NWT Kids Chino Teen Child
      Ralph Lauren Polo Shorts Boys 20 NEW Patchwork Plaid NWT Kids Chino Teen Child
      Opens in a new window or tab
      Brand New
      $20.99
      Was: $34.9940% off
      or Best Offer
      +$5.99 delivery
      Sponsored
    • Tommy Hilfiger Boys Sz 20 Shorts Blue Flat Front Chino 100% Cotton Preppy Summer
      Tommy Hilfiger Boys Sz 20 Shorts Blue Flat Front Chino 100% Cotton Preppy Summer
      Opens in a new window or tab
      Pre-Owned
      $13.00
      or Best Offer
      +$7.00 delivery
      Free returns
      Extra 10% off with coupon
      Sponsored
      Top Rated Plus
    • Vineyard Vines Size 14 Blue Boys Performance Shorts! NWT! Great Buy!
      Vineyard Vines Size 14 Blue Boys Performance Shorts! NWT! Great Buy!
      Opens in a new window or tab
      Pre-Owned
      $22.00
      or Best Offer
      +$8.84 delivery
      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 left5d 11h
      $24.70
      Buy It Now
      +$10.00 delivery
      Sponsored
    • jcrew crewcuts size 14 blue plaid dock style shorts
      jcrew crewcuts size 14 blue plaid dock style shorts
      Opens in a new window or tab
      Pre-Owned
      $9.00
      0 bids · Time left5d 11h
      $11.70
      Buy It Now
      +$6.84 delivery
      Sponsored
    • Vineyard Vines Boys Shorts Seersucker Party Breaker Short 14 Sailors Red Blue
      Vineyard Vines Boys Shorts Seersucker Party Breaker Short 14 Sailors Red Blue
      Opens in a new window or tab
      Brand New
      $21.24
      Was: $24.9915% off
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      +$4.57 delivery
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    • 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
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      +$5.95 delivery
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    • 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
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      +$4.84 delivery
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    • 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
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    • Polo Ralph Lauren Boys Chino Shorts Navy Blue NWT Size 14 Youth Kids Preppy
      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
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    • Brand New with tags- Abercrombie Kids- Boys Khaki Shorts- Size 13/14
      Brand New with tags- Abercrombie Kids- Boys Khaki Shorts- Size 13/14
      Opens in a new window or tab
      Brand New
      $15.00
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    • 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
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      +$5.99 delivery in 2-4 days
      Free returns
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    • Boys Levis 511 Blue Jean Denim Shorts Size 10 Dark/Medium Wash
      Boys Levis 511 Blue Jean Denim Shorts Size 10 Dark/Medium Wash
      Opens in a new window or tab
      Pre-Owned
      $7.95
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      +$5.62 delivery
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    • Boys Ralph Lauren Classic Polo Chino Shorts White With Navy Ponys Sz 20
      Boys Ralph Lauren Classic Polo Chino Shorts White With Navy Ponys Sz 20
      Opens in a new window or tab
      Pre-Owned
      $16.19
      Was: $17.9910% off
      or Best Offer
      +$6.05 delivery
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    • Vineyard Vines Boys Shorts Size 20 Chino Coral Flat Front Cotton Youth
      Vineyard Vines Boys Shorts Size 20 Chino Coral Flat Front Cotton Youth
      Opens in a new window or tab
      Pre-Owned
      $14.99
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      +$6.00 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
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      +$7.01 delivery
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    • 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
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      Pre-Owned
      $14.00
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    • 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
      $37.50
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      Free returns
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    • POLO Ralph Lauren Boys Sz 20 Cargo Shorts Beige Khaki Classic Chino Cotton
      POLO Ralph Lauren Boys Sz 20 Cargo Shorts Beige Khaki Classic Chino Cotton
      Opens in a new window or tab
      Pre-Owned
      $17.09
      Was: $18.9910% off
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    • 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
      $19.99
      Was: $39.9950% off
      or Best Offer
      +$7.35 delivery
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    • Vineyard Vines Shorts Boys size 14 Khaki Adjustable Waist
      Vineyard Vines Shorts Boys size 14 Khaki Adjustable Waist
      Opens in a new window or tab
      Pre-Owned
      $15.00
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      +$5.49 delivery
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    • NWT Chubbies Boys  XS Stretch Short Khakinators Tan Khakis Uniform Preppy
      NWT Chubbies Boys XS Stretch Short Khakinators Tan Khakis Uniform Preppy
      Opens in a new window or tab
      Brand New
      $30.00
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    • Vineyard Vines Boys Classic Fit Club Shorts, size 14, Stone, NWT
      Vineyard Vines Boys Classic Fit Club Shorts, size 14, Stone, NWT
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      $20.00
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    • Polo Ralph Lauren Shorts Boys Size 14 Youth Khaki Beige Cargo Hiking Pockets
      Polo Ralph Lauren Shorts Boys Size 14 Youth Khaki Beige Cargo Hiking Pockets
      Opens in a new window or tab
      Pre-Owned
      $12.98
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    • NWOT Gap Kids Boys Stretch Twill Shorts Navy Blue Sz M (8) 98%cotton 2% spandex
      NWOT Gap Kids Boys Stretch Twill Shorts Navy Blue Sz M (8) 98%cotton 2% spandex
      Opens in a new window or tab
      New (Other)
      $12.95
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      +$6.95 delivery
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    • Polo Ralph Lauren Boys Madras Patchwork Plaid Shorts Size 20 Preppy
      Polo Ralph Lauren Boys Madras Patchwork Plaid Shorts Size 20 Preppy
      Opens in a new window or tab
      Pre-Owned
      $16.98
      or Best Offer
      +$4.99 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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    • 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 left6d 16h
      or Best Offer
      +$4.84 delivery
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    • 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
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    • Polo Ralph Lauren Shorts Boys Size 20 Multicolor Plaid Patchwork Madra Bermuda
      Polo Ralph Lauren Shorts Boys Size 20 Multicolor Plaid Patchwork Madra Bermuda
      Opens in a new window or tab
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