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421 results

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    • Season: Not SpecifiedRemove filter
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    • JANIE & JACK Boys Striped Seersucker Capri Blue Shorts 10 Preppy Casual Classic
      JANIE & JACK Boys Striped Seersucker Capri Blue Shorts 10 Preppy Casual Classic
      Opens in a new window or tab
      Pre-Owned
      $17.60
      Was: $22.0020% off
      or Best Offer
      +$4.84 delivery
      Sponsored
    • Polo Ralph Lauren Shorts Boys 12 Blue Chino Preppy Childrenswear Youth School
      Polo Ralph Lauren Shorts Boys 12 Blue Chino Preppy Childrenswear Youth School
      Opens in a new window or tab
      Pre-Owned
      $14.75
      or Best Offer
      +$6.40 delivery
      Free returns
      Sponsored
    • Gap Kids Shorts Boys 18 Husky Chino Cotton Stretch Flat Front Lot of 4 Gray Blue
      Gap Kids Shorts Boys 18 Husky Chino Cotton Stretch Flat Front Lot of 4 Gray Blue
      Opens in a new window or tab
      Pre-Owned
      $21.59
      Was: $26.9920% off
      or Best Offer
      +$29.68 delivery
      Sponsored
    • Lacoste Boys Two Tone White/ Olive Green Logo Sweat Shorts W/Pockets Kids Sz 10
      Lacoste Boys Two Tone White/ Olive Green Logo Sweat Shorts W/Pockets Kids Sz 10
      Opens in a new window or tab
      Pre-Owned
      $25.00
      or Best Offer
      +$8.54 delivery
      Sponsored
    • EUC Lot Of 4 Boys Sonoma Size 10-12 Pull On Shorts Soft Cotton
      Find similar itemsSee all the items on eBay that match this style
      EUC Lot Of 4 Boys Sonoma Size 10-12 Pull On Shorts Soft Cotton
      Opens in a new window or tab
      Pre-Owned
      $16.00
      Buy It Now
      +$8.71 delivery
      Sponsored
    • 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
      $1.99
      0 bids · Time left7h 13m
      +$6.99 delivery
      Free returns
      Sponsored
      Top Rated Plus
    • Lot of 9 Boy's Youth Small 7 8 Athletic Shorts Adidas New Balance Nike Reebok
      Lot of 9 Boy's Youth Small 7 8 Athletic Shorts Adidas New Balance Nike Reebok
      Opens in a new window or tab
      Pre-Owned
      $50.00
      or Best Offer
      +$15.71 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 (2,021) 99.6%
        • 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%
        • NAUTICA Shorts Boys Size 18 Beige Chino Anchor School Uniform Boat Preppy
          NAUTICA Shorts Boys Size 18 Beige Chino Anchor School Uniform Boat Preppy
          Opens in a new window or tab
          $19.50
          tommycshop (1,564) 100%
    • NEW Crown & Ivy Kids Boys Pink Shorts Size 20 Regular Adjustable Waist NWT
      NEW Crown & Ivy Kids Boys Pink Shorts Size 20 Regular Adjustable Waist NWT
      Opens in a new window or tab
      Brand New
      $16.99
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      +$8.99 delivery
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    • Polo Ralph Lauren Sailboat Terry Lightweight Shorts Boy Size Large 14-16
      Polo Ralph Lauren Sailboat Terry Lightweight Shorts Boy Size Large 14-16
      Opens in a new window or tab
      Brand New
      $25.00
      Buy It Now
      Free delivery
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    • Polo Ralph Lauren Boys Madras Plaid Preppy Cotton Shorts Sz 12 (26x9)
      Polo Ralph Lauren Boys Madras Plaid Preppy Cotton Shorts Sz 12 (26x9)
      Opens in a new window or tab
      Pre-Owned
      $25.00
      or Best Offer
      +$6.40 delivery
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    • 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
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      +$5.00 delivery
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    • 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
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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
      Extra 15% off with coupon
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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
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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
    • 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
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    • Nike Boys Large Tour Performance Golf Shorts Dri Fit Green Gray Plaid
      Nike Boys Large Tour Performance Golf Shorts Dri Fit Green Gray Plaid
      Opens in a new window or tab
      Pre-Owned
      $20.00
      or Best Offer
      +$4.84 delivery
      Sponsored
    • POLO Ralph Lauren Y2K Boys Size 6 Color Block Cotton Fleece Shorts with Logo EUC
      POLO Ralph Lauren Y2K Boys Size 6 Color Block Cotton Fleece Shorts with Logo EUC
      Opens in a new window or tab
      Pre-Owned
      $23.00
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      +$4.71 delivery
      Free returns
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    • RALPH LAUREN POLO Shorts Boy's Sz 16 Light Blue Pony Logo Flat Front Cotton
      RALPH LAUREN POLO Shorts Boy's Sz 16 Light Blue Pony Logo Flat Front Cotton
      Opens in a new window or tab
      Pre-Owned
      $9.99
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      +$5.90 delivery
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    • Crewcuts Factory Pink Shorts Boy’s Size 10 Cotton Adjustable Waist Preppy Easter
      Crewcuts Factory Pink Shorts Boy’s Size 10 Cotton Adjustable Waist Preppy Easter
      Opens in a new window or tab
      Pre-Owned
      $20.00
      or Best Offer
      +$6.99 delivery
      Extra 15% off with coupon
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    • Polo Ralph Lauren Shorts Boys 12 White Cotton Preppy Pockets Pull on Casual
      Polo Ralph Lauren Shorts Boys 12 White Cotton Preppy Pockets Pull on Casual
      Opens in a new window or tab
      Pre-Owned
      $15.99
      or Best Offer
      +$7.25 delivery
      Sponsored
    • NWT Polo Ralph Lauren $50 Big Boy's Chino Drawstring Short, Newport Navy, Sz L
      NWT Polo Ralph Lauren $50 Big Boy's Chino Drawstring Short, Newport Navy, Sz L
      Opens in a new window or tab
      Brand New
      $29.99
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    • POLO Ralph Lauren Lot of 2 Boys Shorts Size 16 Madras & Embroidered Chino EUC
      POLO Ralph Lauren Lot of 2 Boys Shorts Size 16 Madras & Embroidered Chino EUC
      Opens in a new window or tab
      Pre-Owned
      $15.00
      0 bids · Time left1d 5h
      $21.00
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    • Crewcuts Shorts Boy’s Size 5 Cotton Adjustable Waist Preppy - Easter - Purple
      Crewcuts Shorts Boy’s Size 5 Cotton Adjustable Waist Preppy - Easter - Purple
      Opens in a new window or tab
      Pre-Owned
      $11.00
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    • NWT Boy’s Polo Ralph Lauren Khaki Pants “Basic Sand” Sz 8 preppy classic
      NWT Boy’s Polo Ralph Lauren Khaki Pants “Basic Sand” Sz 8 preppy classic
      Opens in a new window or tab
      Brand New
      $26.00
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      +$3.99 delivery
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    • Vineyard Vines Shorts Size S Kids
      Vineyard Vines Shorts Size S Kids
      Opens in a new window or tab
      Pre-Owned
      $1.99
      0 bids · Time left6d 6h
      $4.00
      Buy It Now
      +$4.84 delivery
      Sponsored
    • 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 left1d 6h
      $23.40
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      +$8.71 delivery
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    • Vineyard Vines Boy's Khaki Embroidered Whale Shorts Size 16 – Preppy Chino Style
      Vineyard Vines Boy's Khaki Embroidered Whale Shorts Size 16 – Preppy Chino Style
      Opens in a new window or tab
      New (Other)
      $7.50
      or Best Offer
      +$8.71 delivery
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    • Vineyard Vines Shorts Boys 12 Mint Green Flat Front Breaker Club Golf Chinos
      Vineyard Vines Shorts Boys 12 Mint Green Flat Front Breaker Club Golf Chinos
      Opens in a new window or tab
      Pre-Owned
      $10.35
      Was: $23.0055% off
      or Best Offer
      +$9.00 delivery
      Free returns
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      Top Rated Plus
    • Katin USA Boys Kord Patio Short Youth Lg 14-16 Tan Pull On Surf California Coast
      Katin USA Boys Kord Patio Short Youth Lg 14-16 Tan Pull On Surf California Coast
      Opens in a new window or tab
      Pre-Owned
      $17.99
      Was: $29.9940% off
      Buy It Now
      +$5.99 delivery in 2-4 days
      Free returns
      Sponsored
      Top Rated Plus
    • 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
      $13.99
      Was: $19.9930% off
      or Best Offer
      +$6.99 delivery in 2-4 days
      Free returns
      Extra 15% off with coupon
      Sponsored
      Top Rated Plus
    • Polo Ralph Lauren Chino Shorts Youth 18 28x10 Pink Corduroy Sailboats AOP
      Polo Ralph Lauren Chino Shorts Youth 18 28x10 Pink Corduroy Sailboats AOP
      Opens in a new window or tab
      Pre-Owned
      $9.74
      Was: $12.9925% off
      or Best Offer
      +$5.95 delivery
      Free returns
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      Top Rated Plus
    • 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
      Buy It Now
      +$4.57 delivery
      Free returns
      Sponsored
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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
      $15.99
      or Best Offer
      +$4.84 delivery
      Sponsored
    • Old Navy Plain Front Khaki Chino Shorts Preppy 12" Inseam - Size Boy's 16
      Old Navy Plain Front Khaki Chino Shorts Preppy 12" Inseam - Size Boy's 16
      Opens in a new window or tab
      Pre-Owned
      $11.99
      or Best Offer
      +$7.35 delivery
      Sponsored
    • Polo Ralph Lauren Plaid Patchwork Madras Chino Shorts Boys Size 8 Preppy
      Polo Ralph Lauren Plaid Patchwork Madras Chino Shorts Boys Size 8 Preppy
      Opens in a new window or tab
      Pre-Owned
      $13.99
      Buy It Now
      +$4.84 delivery
      Sponsored
    • Murrays Toggery Shop Boys Sz 10 Shorts Nantucket Reds Cotton Adjustable Waist
      Murrays Toggery Shop Boys Sz 10 Shorts Nantucket Reds Cotton Adjustable Waist
      Opens in a new window or tab
      Pre-Owned
      $24.00
      or Best Offer
      Free delivery
      Free returns
      Sponsored
      Top Rated Plus
    • Polo by Ralph Lauren Boys Navy Blue Flat Front Cotton Chino Shorts 6X Preppy
      Polo by Ralph Lauren Boys Navy Blue Flat Front Cotton Chino Shorts 6X Preppy
      Opens in a new window or tab
      Pre-Owned
      $25.00
      or Best Offer
      +$6.40 delivery
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    • GAP Kids Easy Fit Shorts Youth 10 Blue Chino Long Adjust Waist School Uniform
      GAP Kids Easy Fit Shorts Youth 10 Blue Chino Long Adjust Waist School Uniform
      Opens in a new window or tab
      Pre-Owned
      $15.99
      or Best Offer
      +$6.98 delivery
      Free returns
      Sponsored
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    • NWT Vineyard Vines Boy's Stone Beige Flat Front Stretch Breaker Shorts sz 10
      NWT Vineyard Vines Boy's Stone Beige Flat Front Stretch Breaker Shorts sz 10
      Opens in a new window or tab
      Brand New
      $28.00
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      +$5.49 delivery
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    • Nautica Shorts Youth 10 Turquoise Chino Casual Cotton Preppy Kids
      Nautica Shorts Youth 10 Turquoise Chino Casual Cotton Preppy Kids
      Opens in a new window or tab
      Pre-Owned
      $5.00
      Buy It Now
      +$4.52 delivery in 2-4 days
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    • VTG Polo Ralph Lauren Shorts Boys 12 White BIG Pony 3 Preppy Bermuda Chino Patch
      VTG Polo Ralph Lauren Shorts Boys 12 White BIG Pony 3 Preppy Bermuda Chino Patch
      Opens in a new window or tab
      Pre-Owned
      $29.99
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      +$5.98 delivery
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    • 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
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      +$5.99 delivery
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    • Abercrombie Kids Khaki Shorts Sz 12 Board Skater Vintage Preppy Teen Tween Y2K
      Abercrombie Kids Khaki Shorts Sz 12 Board Skater Vintage Preppy Teen Tween Y2K
      Opens in a new window or tab
      Pre-Owned
      $15.99
      or Best Offer
      +$9.25 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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    • 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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      +$4.84 delivery
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    • Polo Ralph Lauren Blue Spa Terry Shorts Boy’s Size L 14-16 Large Drawstring NWT
      Polo Ralph Lauren Blue Spa Terry Shorts Boy’s Size L 14-16 Large Drawstring NWT
      Opens in a new window or tab
      Brand New
      $39.90
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      +$7.35 delivery
      12 watchers
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    • J.Crew Boys Crewcuts Active Shorts Size 8 Brown Tan Outdoors Training Preppy
      J.Crew Boys Crewcuts Active Shorts Size 8 Brown Tan Outdoors Training Preppy
      Opens in a new window or tab
      Pre-Owned
      $20.99
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    • Crewcuts Shorts Boy’s Size 2 Cotton Adjustable Waist Preppy - Easter - Purple
      Crewcuts Shorts Boy’s Size 2 Cotton Adjustable Waist Preppy - Easter - Purple
      Opens in a new window or tab
      Pre-Owned
      $11.00
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      Free delivery
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    • Vineyard Vines Boys Light Khaki Breaker Chino Casual Shorts Adjustable Waist 16
      Vineyard Vines Boys Light Khaki Breaker Chino Casual Shorts Adjustable Waist 16
      Opens in a new window or tab
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      +$5.80 delivery
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    • POLO RALPH LAUREN BOYS KIDS MADRAS PATCHWORK PLAID SHORTS SZ 8 PREPPY COTTON
      POLO RALPH LAUREN BOYS KIDS MADRAS PATCHWORK PLAID SHORTS SZ 8 PREPPY COTTON
      Opens in a new window or tab
      Pre-Owned
      $27.19
      Was: $33.9920% off
      or Best Offer
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    • 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
      $17.62
      Was: $18.957% off
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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 Boys Fleece Shorts XL 18/20 Colorblock Blue Green Yellow
      Polo Ralph Lauren Boys Fleece Shorts XL 18/20 Colorblock Blue Green Yellow
      Opens in a new window or tab
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      $18.99
      or Best Offer
      +$4.84 delivery
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    • Old Navy Shorts  Lot Of 3 Boys Size 12 Chino Preppy Schoolcore Minimalist Casual
      Old Navy Shorts Lot Of 3 Boys Size 12 Chino Preppy Schoolcore Minimalist Casual
      Opens in a new window or tab
      Brand New
      $31.99
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      +$9.99 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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    • NEW POLO RALPH LAUREN CHAMBRAY PREPPY COTTON SHORTS BOYS SZ 16
      NEW POLO RALPH LAUREN CHAMBRAY PREPPY COTTON SHORTS BOYS SZ 16
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      $30.00
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      +$4.00 delivery
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    • Vinyard Vines BOYS french terry shorts Size 6 PREPPY pink NWT
      Vinyard Vines BOYS french terry shorts Size 6 PREPPY pink NWT
      Opens in a new window or tab
      Brand New
      $29.99
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    • Polo Ralph Lauren Shorts Boys Youth XL 18-20 Blue 2012 Olympics Sweatshorts Logo
      Polo Ralph Lauren Shorts Boys Youth XL 18-20 Blue 2012 Olympics Sweatshorts Logo
      Opens in a new window or tab
      Pre-Owned
      $14.99
      or Best Offer
      +$6.99 delivery
      Free returns
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    • BNWT Vineyard Vines Boys 10 Tan Breaker Short Classic Preppy Very Nice Quality
      BNWT Vineyard Vines Boys 10 Tan Breaker Short Classic Preppy Very Nice Quality
      Opens in a new window or tab
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      $19.99
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      +$6.75 delivery
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    • 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
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      +$4.84 delivery
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    • Gap Shorts Boys Size 10 Husky Brown Chino Khaki Preppy Youth Kids
      Gap Shorts Boys Size 10 Husky Brown Chino Khaki Preppy Youth Kids
      Opens in a new window or tab
      Brand New
      $5.66
      Was: $18.8870% off
      or Best Offer
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      New (Other)
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      Was: $18.0020% off
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      Pre-Owned
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