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    • PreppyRemove filter
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    • 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
    • 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
    • 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
    • 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
      Sponsored
      Top Rated Plus
    • 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
      or Best Offer
      +$6.25 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
    • 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
      Buy It Now
      Free delivery in 2-4 days
      Free returns
      Save up to 30% when you buy more
      Sponsored
    • Boys Shorts Size 7-8 Cargo Summer Lee Dungarees Gap Kids Urban Pipeline Lot of 3
      Boys Shorts Size 7-8 Cargo Summer Lee Dungarees Gap Kids Urban Pipeline Lot of 3
      Opens in a new window or tab
      Pre-Owned
      $25.00
      Buy It Now
      +$8.24 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%
        • 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%
        • 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 (55,977) 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 (2,245) 100%
        • Shorts Chino Capri Bermuda Shorts Children Boys 30057
          Shorts Chino Capri Bermuda Shorts Children Boys 30057
          Opens in a new window or tab
          $35.50
          pbezler (55,977) 100%
    • Polo Ralph Lauren Boys 5 Seersucker Shorts Blue White Adj Waist EUC
      Polo Ralph Lauren Boys 5 Seersucker Shorts Blue White Adj Waist EUC
      Opens in a new window or tab
      Pre-Owned
      $17.00
      Buy It Now
      +$5.00 delivery
      11 watchers
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    • UA Match Play Boys' Shorts Size Youth Medium Navy Blue Lightweight Golf Preppy
      UA Match Play Boys' Shorts Size Youth Medium Navy Blue Lightweight Golf Preppy
      Opens in a new window or tab
      Pre-Owned
      $19.00
      or Best Offer
      +$6.40 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
    • Under Armour Loose Fit Shorts Lot Of 2 Boys Youth M Stretch Logo Heatgear Preppy
      Under Armour Loose Fit Shorts Lot Of 2 Boys Youth M Stretch Logo Heatgear Preppy
      Opens in a new window or tab
      Pre-Owned
      $19.95
      Buy It Now
      +$8.95 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 2-4 days
      Free returns
      Extra 10% off with coupon
      Sponsored
      Top Rated Plus
    • Crewcuts Shorts Boys Size 7 Green Fish Pattern Playful Coastal Preppy Casual
      Crewcuts Shorts Boys Size 7 Green Fish Pattern Playful Coastal Preppy Casual
      Opens in a new window or tab
      Pre-Owned
      $16.89
      or Best Offer
      +$7.99 delivery
      Free returns
      Sponsored
      Top Rated Plus
    • 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
    • Polo Ralph Lauren Jean Shorts Youth Boys Blue Denim Size 14
      Polo Ralph Lauren Jean Shorts Youth Boys Blue Denim Size 14
      Opens in a new window or tab
      Pre-Owned
      $12.00
      or Best Offer
      +$13.20 delivery
      Sponsored
    • Jumping Beans Boys Athletic Shorts Sz 7 Lot
      Jumping Beans Boys Athletic Shorts Sz 7 Lot
      Opens in a new window or tab
      Pre-Owned
      $25.00
      or Best Offer
      +$7.35 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
    • The Children’s Place Boy’s Size 5 T Olive Green Khaki Shorts
      The Children’s Place Boy’s Size 5 T Olive Green Khaki Shorts
      Opens in a new window or tab
      Pre-Owned
      $7.00
      or Best Offer
      +$4.71 delivery
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    • Vineyard Vines Boy’s Size 7 Beige Whale Shorts American Flag Adjustable Waist
      Vineyard Vines Boy’s Size 7 Beige Whale Shorts American Flag Adjustable Waist
      Opens in a new window or tab
      Pre-Owned
      $15.99
      or Best Offer
      +$5.99 delivery
      Sponsored
    • 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
      Buy It Now
      Free delivery
      Free returns
      Save up to 30% when you buy more
      Sponsored
    • Polo Ralph Lauren Vintage Shorts Boys Size 5 Navy Plaid Chino Preppy Logo
      Polo Ralph Lauren Vintage Shorts Boys Size 5 Navy Plaid Chino Preppy Logo
      Opens in a new window or tab
      Pre-Owned
      $10.00
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      +$5.00 delivery
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    • 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
      Opens in a new window or tab
      Pre-Owned
      $20.00
      or Best Offer
      +$14.00 delivery
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    • Janie and Jack Boys Size 7 / Plaid Short, adjustable waist, Field Green and Navy
      Janie and Jack Boys Size 7 / Plaid Short, adjustable waist, Field Green and Navy
      Opens in a new window or tab
      Pre-Owned
      $8.99
      or Best Offer
      +$4.99 delivery in 2-4 days
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    • J Crew Crewcuts Boys Classic Chino Bermuda Shorts Blue Adjustable Waist Size 7
      J Crew Crewcuts Boys Classic Chino Bermuda Shorts Blue Adjustable Waist Size 7
      Opens in a new window or tab
      Pre-Owned
      $15.44
      or Best Offer
      +$5.54 delivery
      Free returns
      Sponsored
      Top Rated Plus
    • 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
    • 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
    • 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
      Sponsored
    • Boys Sz 7 POLO Ralph Lauren Summer Lot Paint Splatter Bermuda Polo Shorts
      Boys Sz 7 POLO Ralph Lauren Summer Lot Paint Splatter Bermuda Polo Shorts
      Opens in a new window or tab
      Pre-Owned
      $55.00
      Buy It Now
      +$6.84 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
      Sponsored
      Top Rated Plus
    • JANIE AND JACK BLACK SHORTS BOYS SIZE 7 PERFORMANCE STRETCH
      JANIE AND JACK BLACK SHORTS BOYS SIZE 7 PERFORMANCE STRETCH
      Opens in a new window or tab
      Pre-Owned
      $18.99
      or Best Offer
      +$6.95 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
    • 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
    • NWT Crewcuts Boys' Spring/Summer Preppy Shorts - Gray - Cotton Size 7
      NWT Crewcuts Boys' Spring/Summer Preppy Shorts - Gray - Cotton Size 7
      Opens in a new window or tab
      Brand New
      $13.95
      Buy It Now
      +$6.95 delivery in 2-4 days
      Sponsored
    • 2010 GAP KIDS Camo Camouflage Cargo Pocket Bermuda Long Shorts 5T 5 Yrs Olive
      2010 GAP KIDS Camo Camouflage Cargo Pocket Bermuda Long Shorts 5T 5 Yrs Olive
      Opens in a new window or tab
      Pre-Owned
      $9.99
      or Best Offer
      +$8.35 delivery in 2-4 days
      Free returns
      Sponsored
      Top Rated Plus
    • 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 19h
      $24.70
      Buy It Now
      +$10.00 delivery
      Sponsored
    • Boys POLO Ralph Lauren Size 7 Seersucker Shorts Blue White  Stripe Adj waist
      Boys POLO Ralph Lauren Size 7 Seersucker Shorts Blue White Stripe Adj waist
      Opens in a new window or tab
      Pre-Owned
      $17.43
      Was: $18.958% off
      or Best Offer
      +$5.25 delivery
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    • 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
    • Polo Ralph Lauren Casual Shorts Boys Size 14 (9" Inseam)
      Polo Ralph Lauren Casual Shorts Boys Size 14 (9" Inseam)
      Opens in a new window or tab
      Pre-Owned
      $20.00
      Was: $25.0020% off
      or Best Offer
      +$7.25 delivery
      Sponsored
    • New Mayoral Boys Tailored Dress Shorts Gray Black Microprint Size 5 (110cm)
      New Mayoral Boys Tailored Dress Shorts Gray Black Microprint Size 5 (110cm)
      Opens in a new window or tab
      Brand New
      $24.44
      or Best Offer
      +$5.54 delivery
      Free returns
      Sponsored
      Top Rated Plus
    • 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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    • 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
      Buy It Now
      +$6.55 delivery
      Sponsored
    • 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
      $12.95
      or Best Offer
      +$8.19 delivery
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    • Polo Ralph Lauren Shorts Boys 7 Khaki Flat Front Classic Polo Chino Stretch
      Polo Ralph Lauren Shorts Boys 7 Khaki Flat Front Classic Polo Chino Stretch
      Opens in a new window or tab
      Pre-Owned
      $14.99
      or Best Offer
      +$4.84 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
      Free returns
      Sponsored
      Top Rated Plus
    • Gap Place Chino Shorts Size 7 Seersucker Blue White Green Shark Print Beach
      Gap Place Chino Shorts Size 7 Seersucker Blue White Green Shark Print Beach
      Opens in a new window or tab
      Pre-Owned
      $12.99
      or Best Offer
      +$5.80 delivery
      Sponsored
    • Ralph Lauren Boys Slim Stretch Embroidered Seersucker Shorts White/Pink Sz 5
      Ralph Lauren Boys Slim Stretch Embroidered Seersucker Shorts White/Pink Sz 5
      Opens in a new window or tab
      Pre-Owned
      $13.50
      or Best Offer
      +$4.84 delivery
      Sponsored
    • Janie and Jack Blue Pull On Linen Shorts Boys Size 14 NWT
      Janie and Jack Blue Pull On Linen Shorts Boys Size 14 NWT
      Opens in a new window or tab
      Brand New
      $17.00
      or Best Offer
      +$6.20 delivery
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    • 2010 OLD NAVY BOYS Mixed Plaid Madras Patchwork Bermuda Trouser Shorts 5 Yrs
      2010 OLD NAVY BOYS Mixed Plaid Madras Patchwork Bermuda Trouser Shorts 5 Yrs
      Opens in a new window or tab
      Pre-Owned
      $7.99
      or Best Offer
      +$6.75 delivery in 2-4 days
      Free returns
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      Top Rated Plus
    • Bundle (4) Boys Shorts Ralph Lauren Carters Dogs Preppy Khaki Navy White 5T
      Bundle (4) Boys Shorts Ralph Lauren Carters Dogs Preppy Khaki Navy White 5T
      Opens in a new window or tab
      Pre-Owned
      $53.00
      Buy It Now
      +$17.55 delivery
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    • Polo Ralph Lauren Boys Blue Chino Shorts, Adjustable Waist, Size 7
      Polo Ralph Lauren Boys Blue Chino Shorts, Adjustable Waist, Size 7
      Opens in a new window or tab
      Pre-Owned
      $15.65
      or Best Offer
      +$4.84 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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    • 2011 GYMBOREE Surf Rocks Drawstring Pull-On Plaid Pocket Long Shorts 5T 5 Yrs
      2011 GYMBOREE Surf Rocks Drawstring Pull-On Plaid Pocket Long Shorts 5T 5 Yrs
      Opens in a new window or tab
      Pre-Owned
      $9.99
      or Best Offer
      +$6.75 delivery in 2-4 days
      Free returns
      Sponsored
      Top Rated Plus
    • Crewcuts Boys Size 5 Shorts Hawaiian Tropical Tech Linen Short Preppy Beach
      Crewcuts Boys Size 5 Shorts Hawaiian Tropical Tech Linen Short Preppy Beach
      Opens in a new window or tab
      Pre-Owned
      $15.99
      or Best Offer
      +$7.95 delivery
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    • 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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    • Lot of 2 Vineyard Vines Boys Embroidered Whale Breaker Shorts 14 EUC Pink Teal
      Lot of 2 Vineyard Vines Boys Embroidered Whale Breaker Shorts 14 EUC Pink Teal
      Opens in a new window or tab
      Pre-Owned
      $19.99
      0 bids · Time left6d 5h
      +$3.49 delivery
      Sponsored
    • Polo Ralph Lauren Lot Of 2 Pairs Cotton Chino Shorts Kids Size 14
      Polo Ralph Lauren Lot Of 2 Pairs Cotton Chino Shorts Kids Size 14
      Opens in a new window or tab
      Pre-Owned
      $10.00
      or Best Offer
      +$10.00 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
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    • 2009 GYMBOREE Spring Car Classic Stripe Seersucker Patchwork Cargo Shorts 5 Yrs
      2009 GYMBOREE Spring Car Classic Stripe Seersucker Patchwork Cargo Shorts 5 Yrs
      Opens in a new window or tab
      Pre-Owned
      $12.99
      or Best Offer
      +$6.75 delivery in 2-4 days
      Free returns
      Sponsored
      Top Rated Plus
    • Janie and Jack Embroidered Pineapple Linen Blend Shorts Sz 7 NEW W/Tag Hawaiian
      Janie and Jack Embroidered Pineapple Linen Blend Shorts Sz 7 NEW W/Tag Hawaiian
      Opens in a new window or tab
      Brand New
      $19.99
      or Best Offer
      +$4.62 delivery
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    • 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
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