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      • Boys' Clothing (Sizes 4 & Up)
        • Selected categoryShorts
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        SMLXL45Filter Applied6781010-12121416Filter Applied1820
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        • Preppy (35) Items (35)
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35 results

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  • New with tags
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    $20.00
    or Best Offer
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    • Fit: Not SpecifiedRemove filter
    • PreppyRemove filter
    • Size: 16Remove filter
    • Size: 5Remove filter
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    • Boys Vineyard Vines Breaker Shorts Size 16 khaki Vacation Trip Preppy
      Boys Vineyard Vines Breaker Shorts Size 16 khaki Vacation Trip Preppy
      Opens in a new window or tab
      Pre-Owned
      $12.50
      or Best Offer
      +$6.99 delivery
      Sponsored
    • Boys Vineyard Vines Hawaiian Print Shorts 100% Cotton Size 16 * Large * X Large
      Boys Vineyard Vines Hawaiian Print Shorts 100% Cotton Size 16 * Large * X Large
      Opens in a new window or tab
      Pre-Owned
      $18.00
      or Best Offer
      +$6.80 delivery
      Sponsored
    • 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
      Free delivery in 2-4 days
      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
      $13.00
      Buy It Now
      +$5.50 delivery
      Sponsored
    • 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
      Sponsored
    • Vineyard Vines NWT Boy’s Size 16 Blue Embroidered Lacrosse Preppy Cotton Shorts
      Vineyard Vines NWT Boy’s Size 16 Blue Embroidered Lacrosse Preppy Cotton Shorts
      Opens in a new window or tab
      Brand New
      $21.00
      or Best Offer
      +$7.35 delivery
      Sponsored
    • 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
      Buy It Now
      Free delivery
      Free returns
      Sponsored
      Top Rated Plus
    • 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
    • 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
      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
      $12.23
      or Best Offer
      +$5.99 delivery
      Free returns
      Sponsored
      Top Rated Plus
    • Strasburg Boys Shorts Size 5 Solid White Dress Preppy NEW
      Strasburg Boys Shorts Size 5 Solid White Dress Preppy NEW
      Opens in a new window or tab
      Brand New
      $20.00
      or Best Offer
      +$7.31 delivery
      Sponsored
    • Wrangler Khakis Cargo Shorts Adjustable Waist Boys 5 And 6 New
      Wrangler Khakis Cargo Shorts Adjustable Waist Boys 5 And 6 New
      Opens in a new window or tab
      Brand New
      $16.99
      Buy It Now
      +$7.35 delivery
      Sponsored
    • Vineyard Vines Boy Stretch Breaker Shorts Size 16 Khaki Chino Preppy New
      Vineyard Vines Boy Stretch Breaker Shorts Size 16 Khaki Chino Preppy New
      Opens in a new window or tab
      Brand New
      $27.99
      or Best Offer
      +$6.95 delivery in 2-4 days
      Free returns
      Sponsored
      Top Rated Plus
    • POLO RALPH LAUREN Boys Belted Bermuda Shorts Size 16 Navy Blue NEW Chino Uniform
      POLO RALPH LAUREN Boys Belted Bermuda Shorts Size 16 Navy Blue NEW Chino Uniform
      Opens in a new window or tab
      New (Other)
      $20.00
      or Best Offer
      +$5.95 delivery
      Extra 15% off with coupon
      Sponsored
    • Polo Ralph Lauren Boys Shorts 16 Preppy Pink Salmon Cotton Adjustable Waist
      Polo Ralph Lauren Boys Shorts 16 Preppy Pink Salmon Cotton Adjustable Waist
      Opens in a new window or tab
      Pre-Owned
      $17.87
      Was: $23.8325% off
      or Best Offer
      +$5.80 delivery
      Free returns
      Extra 10% off with coupon
      Sponsored
      Top Rated Plus
    • 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
    • Abercrombie Kids Shorts Boys Size 16 Grey White Checkered Plaid Preppy Cotton
      Abercrombie Kids Shorts Boys Size 16 Grey White Checkered Plaid Preppy Cotton
      Opens in a new window or tab
      Pre-Owned
      $12.49
      or Best Offer
      +$4.84 delivery
      Sponsored
    • JANIE & JACK Boys Patchwork Shorts 5T Toddler Size 5 ~Navy Blue Plaid
      JANIE & JACK Boys Patchwork Shorts 5T Toddler Size 5 ~Navy Blue Plaid
      Opens in a new window or tab
      Pre-Owned
      $15.00
      Buy It Now
      +$5.50 delivery
      Free returns
      Sponsored
    • Baby Gap Boys 5 Years Chambray Blue Pink & White Striped Preppy Shorts
      Baby Gap Boys 5 Years Chambray Blue Pink & White Striped Preppy Shorts
      Opens in a new window or tab
      Pre-Owned
      $1.99
      Buy It Now
      +$6.55 delivery
      Sponsored
    • Levis Carpenter Shorts Boys 16R Classiccore Blue Denim Normcore Preppy
      Levis Carpenter Shorts Boys 16R Classiccore Blue Denim Normcore Preppy
      Opens in a new window or tab
      Pre-Owned
      $9.00
      or Best Offer
      +$9.99 delivery
      Sponsored
    • Vineyard Vines boys shorts sz 16 blue green plaid VV wakehurst club shorts
      Vineyard Vines boys shorts sz 16 blue green plaid VV wakehurst club shorts
      Opens in a new window or tab
      Brand New
      $44.03
      Was: $55.0420% off
      Buy It Now
      +$9.45 delivery
      Sponsored
    • Levis Cargo Shorts Youth 16 Adjustable waist Khaki Tan Brown Boys Preppy Western
      Levis Cargo Shorts Youth 16 Adjustable waist Khaki Tan Brown Boys Preppy Western
      Opens in a new window or tab
      Pre-Owned
      $17.54
      Was: $21.9320% off
      or Best Offer
      +$8.19 delivery
      Free returns
      Sponsored
      Top Rated Plus
    • Crewcuts Green Embroidered Navy Scorpians Shorts Size 5 Boys Adjustable waist
      Crewcuts Green Embroidered Navy Scorpians Shorts Size 5 Boys Adjustable waist
      Opens in a new window or tab
      Pre-Owned
      $13.80
      Was: $15.008% off
      or Best Offer
      +$4.75 delivery
      Sponsored
    • Hanna Andersson Baggies Striped Terry Shorts Size 110 5 Green White 100% Cotton
      Hanna Andersson Baggies Striped Terry Shorts Size 110 5 Green White 100% Cotton
      Opens in a new window or tab
      Pre-Owned
      $18.00
      Was: $20.0010% off
      or Best Offer
      +$4.84 delivery
      Sponsored
    • Vinyard vines Boys Preppy Shorts
      Vinyard vines Boys Preppy Shorts
      Opens in a new window or tab
      Brand New
      $29.00
      0 bids · Time left5d 1h
      $42.00
      Buy It Now
      +$4.84 delivery
      Sponsored
    • The Childrens Place 4T Bugs Novelty Shorts Orange Pullon Elastic Waistband NEW
      The Childrens Place 4T Bugs Novelty Shorts Orange Pullon Elastic Waistband NEW
      Opens in a new window or tab
      Brand New
      $12.00
      Buy It Now
      +$4.35 delivery
      Sponsored
    • Vtg Polo Ralph Lauren Shorts Chino Khaki Boys Size 16 Beige Preppy Golf Pony
      Vtg Polo Ralph Lauren Shorts Chino Khaki Boys Size 16 Beige Preppy Golf Pony
      Opens in a new window or tab
      Pre-Owned
      $29.99
      or Best Offer
      +$10.10 delivery
      Sponsored
    • Boys Blue Vineyard Vines Preppy Embroidered Cotton Shorts Size 16 EUC
      Boys Blue Vineyard Vines Preppy Embroidered Cotton Shorts Size 16 EUC
      Opens in a new window or tab
      Pre-Owned
      $19.00
      or Best Offer
      +$4.84 delivery
      Sponsored
    • Vineyard Vines Boys Classic Club | Breaker | Blue Twill Shorts Sz 16
      Vineyard Vines Boys Classic Club | Breaker | Blue Twill Shorts Sz 16
      Opens in a new window or tab
      Pre-Owned
      $18.00
      or Best Offer
      +$8.71 delivery
      Sponsored
    • Children’s Place Green Shorts Boys Size 5 Chinos Elastic Cotton Preppy Y2K
      Children’s Place Green Shorts Boys Size 5 Chinos Elastic Cotton Preppy Y2K
      Opens in a new window or tab
      Pre-Owned
      $4.28
      Was: $4.7510% off
      or Best Offer
      +$6.40 delivery
      Sponsored
    • Janie and Jack Boys Size 5 / Plaid Shorts / Cobalt
      Janie and Jack Boys Size 5 / Plaid Shorts / Cobalt
      Opens in a new window or tab
      Pre-Owned
      $12.99
      or Best Offer
      +$4.99 delivery in 2-4 days
      Sponsored
    • Vineyard Vines pink preppy flat front kids 16 long shorts
      Vineyard Vines pink preppy flat front kids 16 long shorts
      Opens in a new window or tab
      Pre-Owned
      $25.00
      or Best Offer
      +$7.79 delivery
      Sponsored
    • Vineyard Vines Boys Gamefish Embroidered Seersucker Shorts Breaker Blue Size 16
      Vineyard Vines Boys Gamefish Embroidered Seersucker Shorts Breaker Blue Size 16
      Opens in a new window or tab
      Brand New
      $39.00
      Buy It Now
      Free delivery
      Free returns
      Sponsored
      Top Rated Plus
    • 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
      Brand New
      $34.49
      Buy It Now
      Free delivery
      Free returns
      Sponsored
      Top Rated Plus
    • Vineyard Vines Blue Embroidered Fish Breaker Shorts size Boy's 16 Coastal Preppy
      Vineyard Vines Blue Embroidered Fish Breaker Shorts size Boy's 16 Coastal Preppy
      Opens in a new window or tab
      Pre-Owned
      $28.00
      or Best Offer
      +$6.00 delivery
      Sponsored
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