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326 results

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    • PreppyRemove filter
    • Size: 24Remove filter
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    • Polo Ralph Lauren Kids Shorts Toddler 4T Green Cotton Preppy
      Polo Ralph Lauren Kids Shorts Toddler 4T Green Cotton Preppy
      Opens in a new window or tab
      Pre-Owned
      $14.39
      Was: $15.9910% off
      or Best Offer
      +$4.84 delivery
      Sponsored
    • NEW Polo Ralph Lauren Madras Plaid Patchwork Plaid Shorts Boys Size 16 Prepster
      NEW Polo Ralph Lauren Madras Plaid Patchwork Plaid Shorts Boys Size 16 Prepster
      Opens in a new window or tab
      Brand New
      $31.49
      Was: $34.9910% off
      or Best Offer
      +$4.84 delivery
      Sponsored
    • Polo Ralph Lauren Boys 16 28 Denim Shorts Dark Wash Dungarees Blue
      Polo Ralph Lauren Boys 16 28 Denim Shorts Dark Wash Dungarees Blue
      Opens in a new window or tab
      Pre-Owned
      $23.08
      Was: $32.9730% off
      or Best Offer
      +$9.99 delivery
      Free returns
      Extra 20% off with coupon
      Sponsored
      Top Rated Plus
    • Polo Ralph Lauren Shorts 16 27 Coral Sullivan Slim Cutoff Denim Pink
      Polo Ralph Lauren Shorts 16 27 Coral Sullivan Slim Cutoff Denim Pink
      Opens in a new window or tab
      Pre-Owned
      $12.51
      Was: $17.8730% off
      or Best Offer
      +$6.49 delivery
      Free returns
      Extra 20% off with coupon
      Sponsored
      Top Rated Plus
    • Vineyard Vines Shorts Boys Size 16 Sailor Red Shorts Stretch NEW
      Find similar itemsSee all the items on eBay that match this style
      Vineyard Vines Shorts Boys Size 16 Sailor Red Shorts Stretch NEW
      Opens in a new window or tab
      Brand New
      $21.99
      or Best Offer
      +$7.99 delivery
      Sponsored
    • Abercrombie Kids Shorts Boys Youth 15 16 blue your personal best  New NWT
      Abercrombie Kids Shorts Boys Youth 15 16 blue your personal best New NWT
      Opens in a new window or tab
      Brand New
      $13.99
      Buy It Now
      Free delivery
      Sponsored
    • Lot Of 7 Pairs Of Boys Shorts Youth Size 16 Hurley Nike Dri-Fit and Old Navy
      Lot Of 7 Pairs Of Boys Shorts Youth Size 16 Hurley Nike Dri-Fit and Old Navy
      Opens in a new window or tab
      Pre-Owned
      $44.00
      or Best Offer
      +$21.20 delivery
      Sponsored
    • Vineyard Vines Boys Blue Lacrosse Embroidered Shorts Size 16 Preppy
      Vineyard Vines Boys Blue Lacrosse Embroidered Shorts Size 16 Preppy
      Opens in a new window or tab
      Pre-Owned
      $20.00
      or Best Offer
      +$14.25 delivery
      Sponsored
    • 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 (1,027) 100%
        • Polo Ralph Lauren Boys Sz 18 Red Sullivan Slim Fit Cut Off Raw Edge Denim Shorts
          Polo Ralph Lauren Boys Sz 18 Red Sullivan Slim Fit Cut Off Raw Edge Denim Shorts
          Opens in a new window or tab
          $24.99
          kusgen123 (19,021) 99.4%
          Last one
        • 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 (2,247) 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
          $15.62
          pbezler (55,991) 99.5%
        • Polo Ralph Lauren Boys Sz 14 Red Sullivan Slim Fit Cut Off Raw Edge Denim Shorts
          Polo Ralph Lauren Boys Sz 14 Red Sullivan Slim Fit Cut Off Raw Edge Denim Shorts
          Opens in a new window or tab
          $24.99
          kusgen123 (19,021) 99.4%
        • Gymboree Boy's Shorts Size 4 Gray Green Plaid 100% Cotton
          Gymboree Boy's Shorts Size 4 Gray Green Plaid 100% Cotton
          Opens in a new window or tab
          $12.44
          kjcouch-1 (8,222) 100%
    • Abercrombie Kids Shorts Boys Youth 15 16 Gray your personal best
      Abercrombie Kids Shorts Boys Youth 15 16 Gray your personal best
      Opens in a new window or tab
      Brand New
      $11.99
      Buy It Now
      Free delivery
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    • Vineyard Vines Adjustable Waist Zip Flat Front Shorts Boys 16 Coral Pockets
      Vineyard Vines Adjustable Waist Zip Flat Front Shorts Boys 16 Coral Pockets
      Opens in a new window or tab
      Pre-Owned
      $15.81
      Was: $19.7620% off
      or Best Offer
      +$5.95 delivery in 2-4 days
      Free returns
      10% off 2+ with coupon
      Sponsored
      Top Rated Plus
    • janie and jack boys new with tags size 16 red elastic waist chino shorts
      janie and jack boys new with tags size 16 red elastic waist chino shorts
      Opens in a new window or tab
      Brand New
      $18.00
      0 bids · Time left4d 23h
      $23.40
      Buy It Now
      +$8.71 delivery
      Sponsored
    • Vineyard Vines Shorts Boys size 16 Seer Sucker Stripe Chino Preppy Yacht Summer
      Vineyard Vines Shorts Boys size 16 Seer Sucker Stripe Chino Preppy Yacht Summer
      Opens in a new window or tab
      Pre-Owned
      $5.00
      0 bids · Time left3d 1h
      $14.00
      Buy It Now
      +$5.65 delivery
      Sponsored
    • Polo Ralph Lauren Bermuda Shorts Boy's Size 16 Blue Emboidered Flags Preppy
      Polo Ralph Lauren Bermuda Shorts Boy's Size 16 Blue Emboidered Flags Preppy
      Opens in a new window or tab
      Pre-Owned
      $11.70
      Was: $13.0010% off
      or Best Offer
      +$5.50 delivery in 2-4 days
      Sponsored
    • Vintage Abercrombie & Fitch Cargo Shorts Youth 16 Red Plaid Heavyweight Y2K 90s
      Vintage Abercrombie & Fitch Cargo Shorts Youth 16 Red Plaid Heavyweight Y2K 90s
      Opens in a new window or tab
      Pre-Owned
      $25.00
      or Best Offer
      +$9.99 delivery in 2-4 days
      Sponsored
    • Polo Ralph Lauren Khaki Shorts Boys 16 Beige Flat Front Chino Casual Youth
      Polo Ralph Lauren Khaki Shorts Boys 16 Beige Flat Front Chino Casual Youth
      Opens in a new window or tab
      Pre-Owned
      $16.87
      or Best Offer
      +$6.49 delivery
      Free returns
      Extra 20% off with coupon
      Sponsored
      Top Rated Plus
    • Evolution In Design Torn Ripped Patches Shorts Boys 16 28x12 Urban Streetwear
      Evolution In Design Torn Ripped Patches Shorts Boys 16 28x12 Urban Streetwear
      Opens in a new window or tab
      Pre-Owned
      $19.99
      or Best Offer
      +$6.99 delivery
      Free returns
      Sponsored
      Top Rated Plus
    • Crewcuts Boys Chino Shorts Size 16 Salmon Preppy Classic Summer Staple School
      Crewcuts Boys Chino Shorts Size 16 Salmon Preppy Classic Summer Staple School
      Opens in a new window or tab
      Brand New
      $14.88
      Buy It Now
      +$9.45 delivery
      Free returns
      Sponsored
      Top Rated Plus
    • Mini Boden Shorts Boy 4Y Blue White  Seersucker Stripe Roll-Up Hem Elastic Waist
      Mini Boden Shorts Boy 4Y Blue White Seersucker Stripe Roll-Up Hem Elastic Waist
      Opens in a new window or tab
      Pre-Owned
      $8.95
      or Best Offer
      +$5.50 delivery
      Free returns
      Sponsored
      Top Rated Plus
    • Gap Kids Flat Front Chino Shorts Boys Size 16 Adjustable Waist Stretch Cotton
      Gap Kids Flat Front Chino Shorts Boys Size 16 Adjustable Waist Stretch Cotton
      Opens in a new window or tab
      Pre-Owned
      $8.94
      or Best Offer
      +$5.99 delivery
      Sponsored
    • Polo Ralph Lauren Seersucker Shorts Stretch Blue/White Classic Fit Size 4 / 4T
      Polo Ralph Lauren Seersucker Shorts Stretch Blue/White Classic Fit Size 4 / 4T
      Opens in a new window or tab
      Brand New
      $20.97
      Buy It Now
      Free delivery in 2-4 days
      Sponsored
    • Polo Ralph Lauren Size 16 Prepster Color Block Four Pocket Boys Shorts
      Polo Ralph Lauren Size 16 Prepster Color Block Four Pocket Boys Shorts
      Opens in a new window or tab
      Brand New
      $24.95
      Buy It Now
      +$7.99 delivery
      Sponsored
    • Polo Ralph Lauren Shorts Boys 16 White All Over Pony Logos Drawstring Preppy Kid
      Polo Ralph Lauren Shorts Boys 16 White All Over Pony Logos Drawstring Preppy Kid
      Opens in a new window or tab
      Pre-Owned
      $18.93
      or Best Offer
      +$7.99 delivery
      Sponsored
    • NEW Boys La Jenns 4T Brown Gingham Shorts Preppy
      NEW Boys La Jenns 4T Brown Gingham Shorts Preppy
      Opens in a new window or tab
      Brand New
      $12.00
      or Best Offer
      +$4.50 delivery
      Extra 30% off with coupon
      Sponsored
    • Vineyard Vines Performance Shorts Boys 16 Pink Breathable
      Vineyard Vines Performance Shorts Boys 16 Pink Breathable
      Opens in a new window or tab
      Pre-Owned
      $11.62
      or Best Offer
      +$5.99 delivery
      Free returns
      Sponsored
      Top Rated Plus
    • Vineyard Vines Shorts Boys 16 White Flat Front Chino Preppy
      Vineyard Vines Shorts Boys 16 White Flat Front Chino Preppy
      Opens in a new window or tab
      Pre-Owned
      $18.45
      or Best Offer
      +$6.95 delivery
      Free returns
      Extra 20% off with coupon
      Sponsored
      Top Rated Plus
    • POLO BY RALPH LAUREN Boys Shorts Madras Plaid Lightweight Preppy Casual SIZE 16
      POLO BY RALPH LAUREN Boys Shorts Madras Plaid Lightweight Preppy Casual SIZE 16
      Opens in a new window or tab
      Pre-Owned
      $16.99
      or Best Offer
      Free delivery
      Sponsored
    • Boy’s Size 16 Gap Kids Khaki Short
      Boy’s Size 16 Gap Kids Khaki Short
      Opens in a new window or tab
      Pre-Owned
      $12.00
      or Best Offer
      +$5.62 delivery
      Sponsored
    • Vintage NOS Boys 16 RALPH LAUREN Shorts Navy Blue $45 POLO 100% Cotton Chinos
      Vintage NOS Boys 16 RALPH LAUREN Shorts Navy Blue $45 POLO 100% Cotton Chinos
      Opens in a new window or tab
      Brand New
      $14.20
      Was: $14.955% off
      Buy It Now
      +$5.80 delivery
      Sponsored
    • POLO RALPH LAUREN Shorts Boys 16 Embroidered Navy Blue Pony AOP Drawstring Prep
      POLO RALPH LAUREN Shorts Boys 16 Embroidered Navy Blue Pony AOP Drawstring Prep
      Opens in a new window or tab
      Pre-Owned
      $15.99
      Was: $19.9920% off
      or Best Offer
      +$5.99 delivery
      Free returns
      Extra 15% off with coupon
      Sponsored
      Top Rated Plus
    • POLO by Ralph Lauren Orange Preppy 100% Cotton Shorts Boy's Size 16
      POLO by Ralph Lauren Orange Preppy 100% Cotton Shorts Boy's Size 16
      Opens in a new window or tab
      Pre-Owned
      $18.00
      or Best Offer
      +$5.75 delivery
      Sponsored
    • Vineyard Vines Yellowfin Plaid Club Shorts Boys 16 Preppy Beach Coastal Chinos
      Vineyard Vines Yellowfin Plaid Club Shorts Boys 16 Preppy Beach Coastal Chinos
      Opens in a new window or tab
      Pre-Owned
      $13.73
      Was: $22.8840% off
      or Best Offer
      +$7.49 delivery
      Free returns
      Sponsored
      Top Rated Plus
    • 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
      Pre-Owned
      $24.99
      Buy It Now
      Free delivery
      Sponsored
    • Chaps Boy’s Bermuda Shorts 4 Madras Red Blue Plaid Adjustable Waist New
      Chaps Boy’s Bermuda Shorts 4 Madras Red Blue Plaid Adjustable Waist New
      Opens in a new window or tab
      Brand New
      $5.99
      or Best Offer
      +$5.85 delivery
      Free returns
      Sponsored
      Top Rated Plus
    • Polo Ralph Lauren Shorts Boys 16 Beige Khaki Cargo 11 Inch Casual Preppy Neutral
      Polo Ralph Lauren Shorts Boys 16 Beige Khaki Cargo 11 Inch Casual Preppy Neutral
      Opens in a new window or tab
      Pre-Owned
      $29.99
      or Best Offer
      +$5.99 delivery
      Free returns
      Extra 10% off with coupon
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      Top Rated Plus
    • NWT Gap Boys Chambray Shorts Youth Size XXL (14-16) Washwell
      NWT Gap Boys Chambray Shorts Youth Size XXL (14-16) Washwell
      Opens in a new window or tab
      Brand New
      $14.99
      or Best Offer
      +$4.84 delivery
      Free returns
      Sponsored
      Top Rated Plus
    • janie and jack boys new with tags size 16 yellow cotton linen chino style shorts
      janie and jack boys new with tags size 16 yellow cotton linen chino style shorts
      Opens in a new window or tab
      Brand New
      $19.99
      0 bids · Time left3d 16h
      $25.99
      Buy It Now
      +$8.71 delivery
      Sponsored
    • Polo Ralph Lauren Boys Size 16 Denim Chino Shorts Blue Jean NWT
      Polo Ralph Lauren Boys Size 16 Denim Chino Shorts Blue Jean NWT
      Opens in a new window or tab
      Brand New
      $21.24
      Was: $24.9915% off
      Buy It Now
      +$6.85 delivery
      Free returns
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      Top Rated Plus
    • Polo Ralph Lauren Boys Sz 18 Red Sullivan Slim Fit Cut Off Raw Edge Denim Shorts
      Polo Ralph Lauren Boys Sz 18 Red Sullivan Slim Fit Cut Off Raw Edge Denim Shorts
      Opens in a new window or tab
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      $24.99
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    • Crewcuts Stanton Chino Shorts Boys Sz 16 Gray Cotton Flat Front NWOT YGI L4-18
      Crewcuts Stanton Chino Shorts Boys Sz 16 Gray Cotton Flat Front NWOT YGI L4-18
      Opens in a new window or tab
      New (Other)
      $22.39
      Was: $31.9930% off
      or Best Offer
      +$6.99 delivery
      Sponsored
    • Vintage O'Neill Shorts Boys 16 Brown Y2K Plaid Chino Skater Surf Punk Rock
      Vintage O'Neill Shorts Boys 16 Brown Y2K Plaid Chino Skater Surf Punk Rock
      Opens in a new window or tab
      Pre-Owned
      $20.00
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      +$5.99 delivery
      Free returns
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    • NEW True Religion Black Jean Shorts Boys 16 Geno Relaxed Slim
      NEW True Religion Black Jean Shorts Boys 16 Geno Relaxed Slim
      Opens in a new window or tab
      Brand New
      $16.97
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    • NWT Polo Ralph Lauren Boys Straight Fit Cotton Classic Chino Shorts, Navy, Sz 16
      NWT Polo Ralph Lauren Boys Straight Fit Cotton Classic Chino Shorts, Navy, Sz 16
      Opens in a new window or tab
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      $24.99
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    • Vineyard Vines Target Youth Boys Whale Logo Patchwork Chino Shorts Preppy XL 16
      Vineyard Vines Target Youth Boys Whale Logo Patchwork Chino Shorts Preppy XL 16
      Opens in a new window or tab
      Pre-Owned
      $14.99
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    • POLO RALPH LAUREN BOYS Bermuda Chino Cargo Khaki Shorts 4 Yrs British Tan
      POLO RALPH LAUREN BOYS Bermuda Chino Cargo Khaki Shorts 4 Yrs British Tan
      Opens in a new window or tab
      Pre-Owned
      $12.99
      or Best Offer
      +$8.35 delivery in 2-3 days
      Free returns
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      Top Rated Plus
    • Gap Camouflage Cargo Shorts Green Drawstring Boys Size 2XL (14-16)
      Gap Camouflage Cargo Shorts Green Drawstring Boys Size 2XL (14-16)
      Opens in a new window or tab
      Brand New
      $20.00
      or Best Offer
      +$6.95 delivery
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    • Vineyard Vines Breaker Shorts Boys Youth 16 Blue Classic Fit Performance Preppy
      Vineyard Vines Breaker Shorts Boys Youth 16 Blue Classic Fit Performance Preppy
      Opens in a new window or tab
      Pre-Owned
      $17.99
      or Best Offer
      +$6.86 delivery
      Sponsored
    • Polo Ralph Lauren Shorts 4T Navy Blue Big Pony Casual Flat Front Chino
      Polo Ralph Lauren Shorts 4T Navy Blue Big Pony Casual Flat Front Chino
      Opens in a new window or tab
      Pre-Owned
      $15.50
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      +$5.80 delivery
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    • Vineyard Vines Boys Breaker Shorts 29 X 9 Chino Whales Jetty Red Embroidered 16
      Vineyard Vines Boys Breaker Shorts 29 X 9 Chino Whales Jetty Red Embroidered 16
      Opens in a new window or tab
      Brand New
      $28.04
      Was: $32.9915% off
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    • Vineyard Vines Khaki Chino Shorts Youth Boys 16 (28 X 9) Beige Cotton Spandex
      Vineyard Vines Khaki Chino Shorts Youth Boys 16 (28 X 9) Beige Cotton Spandex
      Opens in a new window or tab
      Pre-Owned
      $16.95
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      +$6.99 delivery in 2-4 days
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    • Under Armour Boys Loose Heatgear Shorts Size 16 Gray Pockets Logo Zipper NWT
      Under Armour Boys Loose Heatgear Shorts Size 16 Gray Pockets Logo Zipper NWT
      Opens in a new window or tab
      Brand New
      $21.95
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      +$3.99 delivery
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    • Polo Ralph Lauren Chino Khaki Shorts Boys 16 Casual Preppy 10" inseam
      Polo Ralph Lauren Chino Khaki Shorts Boys 16 Casual Preppy 10" inseam
      Opens in a new window or tab
      Pre-Owned
      $13.99
      or Best Offer
      +$7.35 delivery
      Sponsored
    • Polo Ralph Lauren Youth Boys Shorts 16 Blue Bib Pony Preppy Old Money Casual
      Polo Ralph Lauren Youth Boys Shorts 16 Blue Bib Pony Preppy Old Money Casual
      Opens in a new window or tab
      Pre-Owned
      $16.99
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      +$6.99 delivery
      Free returns
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      Top Rated Plus
    • Under Armour Golf Shorts Boys Size 16 Khaki Chino 10” Inseam
      Under Armour Golf Shorts Boys Size 16 Khaki Chino 10” Inseam
      Opens in a new window or tab
      Pre-Owned
      $9.00
      Was: $18.0050% off
      or Best Offer
      +$6.95 delivery
      Free returns
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      Top Rated Plus
    • NWT Polo Ralph Lauren Boys' Paint Splatter Sullivan Slim Denim Shorts Size 16
      NWT Polo Ralph Lauren Boys' Paint Splatter Sullivan Slim Denim Shorts Size 16
      Opens in a new window or tab
      Brand New
      $24.99
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    • Polo Ralph Lauren Boys Stretch Twill Prepster Chino Shorts, Yellow Size 16
      Polo Ralph Lauren Boys Stretch Twill Prepster Chino Shorts, Yellow Size 16
      Opens in a new window or tab
      Pre-Owned
      $16.00
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      +$6.55 delivery
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    • UNDER AMOUR BOYS Size 16 Tan Showdown HeatGear Golf Shorts Lightweight
      UNDER AMOUR BOYS Size 16 Tan Showdown HeatGear Golf Shorts Lightweight
      Opens in a new window or tab
      Pre-Owned
      $18.00
      or Best Offer
      +$8.84 delivery
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    • RALPH LAUREN POLO Boy's Sz 16 Preppy Plaid Shorts Cotton 10.5" Inseam
      RALPH LAUREN POLO Boy's Sz 16 Preppy Plaid Shorts Cotton 10.5" Inseam
      Opens in a new window or tab
      Pre-Owned
      $11.99
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      +$6.50 delivery
      Sponsored
    • Vineyard Vines Shorts Boys Size 16 Patriotic Shorts
      Vineyard Vines Shorts Boys Size 16 Patriotic Shorts
      Opens in a new window or tab
      Brand New
      $17.00
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      +$8.71 delivery
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    • Nike + Polo Ralph Lauren Shorts Boy 4 4T Navy Blue Chino Pocket
      Nike + Polo Ralph Lauren Shorts Boy 4 4T Navy Blue Chino Pocket
      Opens in a new window or tab
      Pre-Owned
      $19.99
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      Free delivery
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    • Abercrombie Kids-Boys Drawstring Sweat Shorts Sz.15-16/Blue/Cotton Blend/Pockets
      Abercrombie Kids-Boys Drawstring Sweat Shorts Sz.15-16/Blue/Cotton Blend/Pockets
      Opens in a new window or tab
      Brand New
      $24.59
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    • New Old Navy boys youth active go dry cool shorts XL 14/16
      New Old Navy boys youth active go dry cool shorts XL 14/16
      Opens in a new window or tab
      Brand New
      $7.99
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      +$5.84 delivery
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    • JANIE AND JACK Boys’ Blue Pink Plaid Linen Blend Shorts Size 4 Preppy Country
      JANIE AND JACK Boys’ Blue Pink Plaid Linen Blend Shorts Size 4 Preppy Country
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