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261 results

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    • PreppyRemove filter
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    • 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
    • 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
      $32.97
      or Best Offer
      +$9.99 delivery
      Free returns
      Sponsored
      Top Rated Plus
    • Vineyard Vines Shorts Anchor Nautical Boys 16 XL EUC
      Vineyard Vines Shorts Anchor Nautical Boys 16 XL EUC
      Opens in a new window or tab
      Pre-Owned
      $14.00
      or Best Offer
      +$4.84 delivery
      Sponsored
    • Eddie Bauer Shorts Boys 16 Khaki Cargo Knee Length Baggy Flat Front Skate Cotton
      Eddie Bauer Shorts Boys 16 Khaki Cargo Knee Length Baggy Flat Front Skate Cotton
      Opens in a new window or tab
      Pre-Owned
      $19.99
      or Best Offer
      +$5.99 delivery
      Free returns
      Extra 15% off with coupon
      Sponsored
      Top Rated Plus
    • Vntg Polo Ralph Lauren Jean Shorts Youth Boys Blue Denim Carpenter Sz 16
      Vntg Polo Ralph Lauren Jean Shorts Youth Boys Blue Denim Carpenter Sz 16
      Opens in a new window or tab
      Brand New
      $19.99
      or Best Offer
      +$8.19 delivery
      Sponsored
    • J Crew Boys Chino Shorts Bleecker Size 16 Khaki Straight Stretch Cotton Casual
      J Crew Boys Chino Shorts Bleecker Size 16 Khaki Straight Stretch Cotton Casual
      Opens in a new window or tab
      Brand New
      $33.24
      or Best Offer
      +$5.80 delivery
      Sponsored
    • Vtg Jean Shorts Tommy Hilfiger Boys 16 Denim Jorts 90s Y2K Flag Logo Carpenter
      Vtg Jean Shorts Tommy Hilfiger Boys 16 Denim Jorts 90s Y2K Flag Logo Carpenter
      Opens in a new window or tab
      Pre-Owned
      $19.99
      Buy It Now
      +$6.99 delivery
      Free returns
      Sponsored
      Top Rated Plus
    • Vineyard Vines Blue Boys Shorts! Size 16! NWT! Great For Any Occasion!
      Vineyard Vines Blue Boys Shorts! Size 16! NWT! Great For Any Occasion!
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      Brand New
      $20.00
      or Best Offer
      +$8.71 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 (1,021) 100%
        • 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
          $15.29
          fre-boon (1,902) 99.8%
        • Polo Ralph Lauren Boys Size 16 Cobalt Blue Classic Elastic Sides Shorts Logo
          Polo Ralph Lauren Boys Size 16 Cobalt Blue Classic Elastic Sides Shorts Logo
          Opens in a new window or tab
          $16.00
          alwaysopen-9 (1,841) 100%
        • Polo Ralph Lauren Big Boys Cotton Denim Cutoff Shorts - Finn Wash Red (Red, 16)
          Polo Ralph Lauren Big Boys Cotton Denim Cutoff Shorts - Finn Wash Red (Red, 16)
          Opens in a new window or tab
          $30.98
          2015market (99,651) 98.9%
    • Vineyard Vines Performance Khaki Tan Shorts Youth Boys Sz. 16  Preppy Whale EUC
      Vineyard Vines Performance Khaki Tan Shorts Youth Boys Sz. 16 Preppy Whale EUC
      Opens in a new window or tab
      Pre-Owned
      $24.99
      or Best Offer
      +$8.71 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
      Opens in a new window or tab
      Pre-Owned
      $20.00
      or Best Offer
      +$14.00 delivery
      Sponsored
    • Properly Tied Boys shorts size 16 Salmon Dress Preppy School
      Properly Tied Boys shorts size 16 Salmon Dress Preppy School
      Opens in a new window or tab
      Pre-Owned
      $13.13
      Was: $17.2724% off
      or Best Offer
      +$6.55 delivery
      Sponsored
    • Gap Kids Shorts Boys Size 16 Gray Chino Stretch Uniform Dressy, NEW
      Gap Kids Shorts Boys Size 16 Gray Chino Stretch Uniform Dressy, NEW
      Opens in a new window or tab
      Brand New
      $15.99
      or Best Offer
      +$6.25 delivery
      Sponsored
    • Polo Ralph Lauren Shorts Chino Boys Youth Size 16 Coral Casual Preppy
      Polo Ralph Lauren Shorts Chino Boys Youth Size 16 Coral Casual Preppy
      Opens in a new window or tab
      Pre-Owned
      $14.00
      or Best Offer
      +$5.99 delivery
      Free returns
      Extra 15% off with coupon
      Sponsored
      Top Rated Plus
    • Vineyard Vines Boys' Breaker Shorts Size 16 Khaki
      Vineyard Vines Boys' Breaker Shorts Size 16 Khaki
      Opens in a new window or tab
      Pre-Owned
      $18.00
      or Best Offer
      +$8.71 delivery
      Sponsored
    • 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
      Sponsored
      Top Rated Plus
    • 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
      $16.02
      Was: $22.8830% off
      or Best Offer
      +$7.49 delivery
      Free returns
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      Top Rated Plus
    • POLO RALPH LAUREN Big Boy Lightweight Parachute Rugby Twill Shorts White Size 16
      POLO RALPH LAUREN Big Boy Lightweight Parachute Rugby Twill Shorts White Size 16
      Opens in a new window or tab
      Pre-Owned
      $17.98
      or Best Offer
      +$8.71 delivery
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    • Abercrombie Fitch Cargo Shorts Youth 16 Red Y2K Utility Faded Outdoors
      Abercrombie Fitch Cargo Shorts Youth 16 Red Y2K Utility Faded Outdoors
      Opens in a new window or tab
      Pre-Owned
      $4.99
      0 bids · Time left3d 23h
      +$6.99 delivery
      Free returns
      Sponsored
      Top Rated Plus
    • Polo Ralph Lauren Boys Size 10/12 Pastel Polo Prepster Drawstring Shorts Pony
      Polo Ralph Lauren Boys Size 10/12 Pastel Polo Prepster Drawstring Shorts Pony
      Opens in a new window or tab
      Pre-Owned
      $19.99
      or Best Offer
      +$5.99 delivery
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    • Boys Wonder Nation Gray Tough Core Drawstring Shorts Size S(6-7) School Approved
      Boys Wonder Nation Gray Tough Core Drawstring Shorts Size S(6-7) School Approved
      Opens in a new window or tab
      Brand New
      $8.50
      Buy It Now
      Free delivery
      44 sold
      Sponsored
    • Vineyard Vines NWT Boys Sz 16 Red Blue Gingham Plaid Breaker Adjustable Shorts
      Vineyard Vines NWT Boys Sz 16 Red Blue Gingham Plaid Breaker Adjustable Shorts
      Opens in a new window or tab
      Brand New
      $29.99
      or Best Offer
      +$8.71 delivery
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    • NWT Polo Ralph Lauren Classic Boys Madras Plaid Preppy Cotton Shorts Sz. 12
      NWT Polo Ralph Lauren Classic Boys Madras Plaid Preppy Cotton Shorts Sz. 12
      Opens in a new window or tab
      Brand New
      $35.00
      or Best Offer
      +$8.24 delivery
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    • POLO RALPH LAUREN Jeans Shorts Youth 16 Sullivan Slim Fit Fray Blue Denim NWT
      POLO RALPH LAUREN Jeans Shorts Youth 16 Sullivan Slim Fit Fray Blue Denim NWT
      Opens in a new window or tab
      Brand New
      $18.85
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      +$6.99 delivery
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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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      +$5.99 delivery
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    • 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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      +$5.99 delivery
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    • NWT Vineyard Vines Boy’s L 16 Chino Jetty Shorts Sage Green RV $39.99 Drawstring
      NWT Vineyard Vines Boy’s L 16 Chino Jetty Shorts Sage Green RV $39.99 Drawstring
      Opens in a new window or tab
      Brand New
      $16.00
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      +$6.50 delivery
      Extra 10% off with coupon
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    • NWT Polo Ralph Lauren The Sullivan Slim Denim Shorts Paint Splatter Size 16 (6)
      NWT Polo Ralph Lauren The Sullivan Slim Denim Shorts Paint Splatter Size 16 (6)
      Opens in a new window or tab
      Brand New
      $33.95
      or Best Offer
      +$5.99 delivery
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    • 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
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    • 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
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    • 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
      $19.99
      or Best Offer
      +$5.99 delivery
      Free returns
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      Top Rated Plus
    • Polo Ralph Lauren Shorts Youth 16 Brown Khaki Tan Cargo Cotton Classic Fit Boys
      Polo Ralph Lauren Shorts Youth 16 Brown Khaki Tan Cargo Cotton Classic Fit Boys
      Opens in a new window or tab
      Pre-Owned
      $24.99
      or Best Offer
      +$6.99 delivery
      Free returns
      Sponsored
      Top Rated Plus
    • Vineyard Vines Chino Shorts Youth Boy Size 16 Blue Shark Embroidered Preppy
      Vineyard Vines Chino Shorts Youth Boy Size 16 Blue Shark Embroidered Preppy
      Opens in a new window or tab
      Pre-Owned
      $16.99
      or Best Offer
      +$7.29 delivery
      Extra 15% off with coupon
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    • Polo Ralph Lauren Boys Sz 16 Red Sullivan Slim Fit Cut Off Raw Edge Denim Shorts
      Polo Ralph Lauren Boys Sz 16 Red Sullivan Slim Fit Cut Off Raw Edge Denim Shorts
      Opens in a new window or tab
      Brand New
      $24.99
      Buy It Now
      Free delivery
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    • NWT Vineyard Vines Boys Ocean Breeze Blue Flat Front Stretch Breaker Shorts 16
      NWT Vineyard Vines Boys Ocean Breeze Blue Flat Front Stretch Breaker Shorts 16
      Opens in a new window or tab
      Brand New
      $14.99
      or Best Offer
      +$7.25 delivery
      Sponsored
    • Gap Boys Flat Front Twill Chino YOU CHOOSE Size & Color NWT
      Gap Boys Flat Front Twill Chino YOU CHOOSE Size & Color NWT
      Opens in a new window or tab
      Brand New
      $11.88
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      +$7.35 delivery
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    • 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
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      Free delivery
      Free returns
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    • Polo Ralph Lauren Core Replen Khaki Pants Size 16
      Polo Ralph Lauren Core Replen Khaki Pants Size 16
      Opens in a new window or tab
      New (Other)
      $25.00
      or Best Offer
      +$18.95 delivery
      Sponsored
    • Childrens Place Cargo Shorts Boys Size 16 Adjustable Waist School Black
      Childrens Place Cargo Shorts Boys Size 16 Adjustable Waist School Black
      Opens in a new window or tab
      Pre-Owned
      $7.75
      Buy It Now
      +$5.80 delivery
      Sponsored
    • Polo Ralph Lauren Boys Size 16 White Embroidered Logo Dress Chino Shorts
      Polo Ralph Lauren Boys Size 16 White Embroidered Logo Dress Chino Shorts
      Opens in a new window or tab
      Pre-Owned
      $11.25
      or Best Offer
      +$6.79 delivery
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    • Polo Ralph Lauren Cargo Shorts Boys Size 16 Tan 10" Inseam Pockets Preppy
      Polo Ralph Lauren Cargo Shorts Boys Size 16 Tan 10" Inseam Pockets Preppy
      Opens in a new window or tab
      Pre-Owned
      $19.99
      or Best Offer
      +$8.99 delivery
      Free returns
      Extra 20% off with coupon
      Sponsored
      Top Rated Plus
    • Childrens Place Boys Shorts 16 Multicolor Cotton Madras Patchwork Adjustable Wst
      Childrens Place Boys Shorts 16 Multicolor Cotton Madras Patchwork Adjustable Wst
      Opens in a new window or tab
      Pre-Owned
      $12.50
      Was: $24.9950% off
      or Best Offer
      +$5.62 delivery
      Sponsored
    • Vineyard Vines Boys Red Embroidered Candy Cane Whale Breaker Shorts 16 3H0227
      Vineyard Vines Boys Red Embroidered Candy Cane Whale Breaker Shorts 16 3H0227
      Opens in a new window or tab
      Brand New
      $56.10
      Was: $66.0015% off
      or Best Offer
      +$6.57 delivery
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    • *** BRAND NEW WITH TAG The Childrens Place TCP Boys size 16 Bermuda Shorts ***
      *** BRAND NEW WITH TAG The Childrens Place TCP Boys size 16 Bermuda Shorts ***
      Opens in a new window or tab
      Brand New
      $9.99
      0 bids · Time left22h 52m
      $16.99
      Buy It Now
      Free delivery
      Sponsored
    • Tommy Bahama Boys Shorts Large 10/12 Blue Pull On Pockets Preppy Casual Outdoor
      Tommy Bahama Boys Shorts Large 10/12 Blue Pull On Pockets Preppy Casual Outdoor
      Opens in a new window or tab
      Pre-Owned
      $9.99
      or Best Offer
      +$5.80 delivery
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    • Vineyard vines performance shorts boys size 14 tan Golf Adjustable Waist
      Vineyard vines performance shorts boys size 14 tan Golf Adjustable Waist
      Opens in a new window or tab
      Pre-Owned
      $15.99
      or Best Offer
      +$8.71 delivery
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    • Tailorbyrd Boys Button Down Shirt Sz 16 Stripe Check L-Sleeve Nautical Sailing
      Tailorbyrd Boys Button Down Shirt Sz 16 Stripe Check L-Sleeve Nautical Sailing
      Opens in a new window or tab
      Pre-Owned
      $16.00
      or Best Offer
      +$5.80 delivery
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    • 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
      $19.99
      0 bids · Time left3d 15h
      $25.99
      Buy It Now
      +$8.71 delivery
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    • Vineyard Vines Shorts Boys Size 16 Gray Breaker Shorts Stretch
      Vineyard Vines Shorts Boys Size 16 Gray Breaker Shorts Stretch
      Opens in a new window or tab
      Brand New
      $17.95
      Was: $19.9510% off
      Buy It Now
      +$5.95 delivery
      Free returns
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    • Polo Ralph Lauren Boys Size 16 Cobalt Blue Classic Elastic Sides Shorts Logo
      Polo Ralph Lauren Boys Size 16 Cobalt Blue Classic Elastic Sides Shorts Logo
      Opens in a new window or tab
      Pre-Owned
      $16.00
      Buy It Now
      Free delivery
      Free returns
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      Top Rated Plus
    • 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
      $11.01
      Was: $12.2310% off
      or Best Offer
      +$5.99 delivery
      Free returns
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    • NEW Vineyard Vines Khaki Tan Hybrid Breaker Shorts Young Size 16 Pocket Bermuda
      NEW Vineyard Vines Khaki Tan Hybrid Breaker Shorts Young Size 16 Pocket Bermuda
      Opens in a new window or tab
      Brand New
      $45.00
      or Best Offer
      +$6.55 delivery
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    • NWT Vineyard Vines Boys' Blue Stretch Breaker Shorts Size 16 Swordfish Sea Turtl
      NWT Vineyard Vines Boys' Blue Stretch Breaker Shorts Size 16 Swordfish Sea Turtl
      Opens in a new window or tab
      Brand New
      $23.00
      or Best Offer
      +$9.45 delivery
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    • Boys Polo Ralph Lauren Straight Fit Twill Khaki Shorts in Basic Sand Size 16
      Boys Polo Ralph Lauren Straight Fit Twill Khaki Shorts in Basic Sand Size 16
      Opens in a new window or tab
      Pre-Owned
      $16.95
      or Best Offer
      +$6.00 delivery
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    • 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
      $10.80
      Was: $18.0040% off
      or Best Offer
      +$6.95 delivery
      Free returns
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    • POLO RALPH LAUREN Boys Shorts Madras Plaid Lightweight Preppy Casual Summer 16
      POLO RALPH LAUREN Boys Shorts Madras Plaid Lightweight Preppy Casual Summer 16
      Opens in a new window or tab
      Pre-Owned
      $12.74
      Was: $14.9915% off
      or Best Offer
      +$6.95 delivery
      Free returns
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    • NWT U.S. Polo Assn Sz16 Rolled Button Cuff Chino Khaki Shorts Adj. Waist Unisex
      NWT U.S. Polo Assn Sz16 Rolled Button Cuff Chino Khaki Shorts Adj. Waist Unisex
      Opens in a new window or tab
      Brand New
      $18.75
      Was: $25.0025% off
      or Best Offer
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    • Vineyard Vines Khaki Chino Shorts Beige Youth Boys Embroidered Cotton Size 16
      Vineyard Vines Khaki Chino Shorts Beige Youth Boys Embroidered Cotton Size 16
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      Pre-Owned
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    • Vineyard Vines Boy's Size 16 Salmon Pink Shorts Performance Golf Chino Shorts
      Vineyard Vines Boy's Size 16 Salmon Pink Shorts Performance Golf Chino Shorts
      Opens in a new window or tab
      Pre-Owned
      $18.99
      or Best Offer
      +$7.35 delivery
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    • 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
      Buy It Now
      +$5.50 delivery
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    • Kids Crown & Ivy Blue  Flat Front Adjustable Shorts Size 16 Preppy, Easter
      Kids Crown & Ivy Blue Flat Front Adjustable Shorts Size 16 Preppy, Easter
      Opens in a new window or tab
      Pre-Owned
      $15.00
      or Best Offer
      +$5.80 delivery
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    • Polo Ralph Lauren Shorts Boys 16 (10” Inseam) Navy Blue Classic Chino Preppy
      Polo Ralph Lauren Shorts Boys 16 (10” Inseam) Navy Blue Classic Chino Preppy
      Opens in a new window or tab
      Pre-Owned
      $17.95
      Was: $19.9510% off
      or Best Offer
      +$7.99 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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    • 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
      or Best Offer
      +$6.85 delivery
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    • Polo Ralph Lauren Cotton Chino Shorts Boys Youth Size 16 Navy Blue New With Tags
      Polo Ralph Lauren Cotton Chino Shorts Boys Youth Size 16 Navy Blue New With Tags
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