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      • Boys' Clothing (Sizes 4 & Up)
        • Selected categoryShorts
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        SMLXL45Filter Applied67Filter Applied810121414-16161820
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        • Preppy (45) Items (45)
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45 results

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    • Free ReturnsRemove filter
    • Size: 5Remove filter
    • Size: 7Remove filter
    • PreppyRemove filter
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    • 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
    • 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
    • Mini Boden Shorts Boys Red Casual Drawstring Size 5Y
      Mini Boden Shorts Boys Red Casual Drawstring Size 5Y
      Opens in a new window or tab
      Pre-Owned
      $10.99
      or Best Offer
      +$5.00 delivery
      Free returns
      Sponsored
      Top Rated Plus
    • New Crewcuts Boys Classic Pinstripe Gramercy Shorts Blue White Seersucker Size 5
      New Crewcuts Boys Classic Pinstripe Gramercy Shorts Blue White Seersucker Size 5
      Opens in a new window or tab
      New (Other)
      $19.44
      or Best Offer
      +$5.54 delivery
      Free returns
      Sponsored
      Top Rated Plus
    • Polo Ralph Lauren Boys Size 5 Chino Adjustable Waist Blue Navy Shorts Preppy
      Polo Ralph Lauren Boys Size 5 Chino Adjustable Waist Blue Navy Shorts Preppy
      Opens in a new window or tab
      Pre-Owned
      $9.00
      Was: $12.0025% off
      Buy It Now
      +$5.50 delivery
      Free returns
      Sponsored
    • 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
    • 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
    • 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
    • 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
      Sponsored
      Top Rated Plus
    • 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
    • 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
    • 2010 GAP KIDS Embroidered Pirate Skull Crossbones Bermuda Shorts 5 Yrs Khaki
      2010 GAP KIDS Embroidered Pirate Skull Crossbones Bermuda Shorts 5 Yrs Khaki
      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
    • Polo Ralph Lauren Boys Size 7 Black Cotton Chino Drawstring Shorts
      Polo Ralph Lauren Boys Size 7 Black Cotton Chino Drawstring Shorts
      Opens in a new window or tab
      Pre-Owned
      $14.99
      or Best Offer
      +$5.10 delivery
      Free returns
      Sponsored
      Top Rated Plus
    • Polo Ralph Lauren Shorts Boys 7 Colorful Chino Preppy Youth School Plaid
      Polo Ralph Lauren Shorts Boys 7 Colorful Chino Preppy Youth School Plaid
      Opens in a new window or tab
      Pre-Owned
      $14.75
      or Best Offer
      +$6.40 delivery
      Free returns
      Sponsored
    • Polo Ralph Lauren Classic Chino Shorts Youth 7 Navy Blue Belted Preppy Kids
      Polo Ralph Lauren Classic Chino Shorts Youth 7 Navy Blue Belted Preppy Kids
      Opens in a new window or tab
      Pre-Owned
      $14.39
      Buy It Now
      +$5.50 delivery
      Free returns
      Sponsored
      Top Rated Plus
    • Tucker & Tate Shorts Boys 5 Tan Chino Cargo Pockets Pull On Utility Knit Waist
      Tucker & Tate Shorts Boys 5 Tan Chino Cargo Pockets Pull On Utility Knit Waist
      Opens in a new window or tab
      Pre-Owned
      $9.99
      or Best Offer
      +$6.99 delivery
      Free returns
      Extra 15% off with coupon
      Sponsored
      Top Rated Plus
    • Janie and Jack Shorts Boy 5 White Green Tennis  Embroidered Twill Preppy Stretch
      Janie and Jack Shorts Boy 5 White Green Tennis Embroidered Twill Preppy Stretch
      Opens in a new window or tab
      Pre-Owned
      $15.99
      or Best Offer
      +$5.75 delivery
      Free returns
      Extra 15% off with coupon
      Sponsored
      Top Rated Plus
    • Janie and Jack Boys Classic Pinstripe Seersucker Shorts Pink and White Size 5
      Janie and Jack Boys Classic Pinstripe Seersucker Shorts Pink and White Size 5
      Opens in a new window or tab
      Pre-Owned
      $15.44
      or Best Offer
      +$5.54 delivery
      Free returns
      Sponsored
      Top Rated Plus
    • 2011 GYMBOREE BOYS Golf Pro Tee Off Patchwork Mixed Plaid Check Shorts 5T 5 Yrs
      2011 GYMBOREE BOYS Golf Pro Tee Off Patchwork Mixed Plaid Check Shorts 5T 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
      Sponsored
      Top Rated Plus
    • Gymboree Boys Classic Seersucker Bermuda Shorts Blue White Pinstripe Size 5
      Gymboree Boys Classic Seersucker Bermuda Shorts Blue White Pinstripe Size 5
      Opens in a new window or tab
      Pre-Owned
      $14.44
      or Best Offer
      +$5.54 delivery
      Free returns
      Sponsored
      Top Rated Plus
    • 2013 OLD NAVY BOYS Classic Plaid Bermuda Summer Shorts 5T 5 Yrs Blue Red Multi
      2013 OLD NAVY BOYS Classic Plaid Bermuda Summer Shorts 5T 5 Yrs Blue Red Multi
      Opens in a new window or tab
      Pre-Owned
      $7.99
      or Best Offer
      +$6.75 delivery in 2-4 days
      Free returns
      Sponsored
      Top Rated Plus
    • 2007 GYMBOREE OUTLET BOYS Resort Getaway Dapper Plaid Bermuda Shorts 5 Yrs Blue
      2007 GYMBOREE OUTLET BOYS Resort Getaway Dapper Plaid Bermuda Shorts 5 Yrs Blue
      Opens in a new window or tab
      Pre-Owned
      $6.99
      or Best Offer
      +$6.75 delivery in 2-4 days
      Free returns
      Sponsored
      Top Rated Plus
    • VTG 2004 GAP KIDS Durable Goods Cargo Pocket Bermuda Shorts 5T 5 Yrs Moss Green
      VTG 2004 GAP KIDS Durable Goods Cargo Pocket Bermuda Shorts 5T 5 Yrs Moss Green
      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
    • Polo Ralph Lauren Shorts Boys 7 Blue Straight Leg Preppy Casual Pockets Cotton
      Polo Ralph Lauren Shorts Boys 7 Blue Straight Leg Preppy Casual Pockets Cotton
      Opens in a new window or tab
      Pre-Owned
      $20.00
      or Best Offer
      +$7.65 delivery
      Free returns
      Sponsored
      Top Rated Plus
    • 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
    • Adidas Shorts Boys 14/16 Linear Logo Black Elastic Waistband Activewear Stretch
      Adidas Shorts Boys 14/16 Linear Logo Black Elastic Waistband Activewear Stretch
      Opens in a new window or tab
      Pre-Owned
      $18.00
      or Best Offer
      +$7.99 delivery
      Free returns
      Sponsored
    • 2010 GAP KIDS FACTORY Beach Resort Madras Plaid Bermuda Shorts 5 Yrs Light Blue
      2010 GAP KIDS FACTORY Beach Resort Madras Plaid Bermuda Shorts 5 Yrs Light Blue
      Opens in a new window or tab
      Pre-Owned
      $5.99
      or Best Offer
      +$6.75 delivery in 2-4 days
      Free returns
      Sponsored
      Top Rated Plus
    • HAWK Gray Checkered Preppy Shorts Youth Boys Size 7
      HAWK Gray Checkered Preppy Shorts Youth Boys Size 7
      Opens in a new window or tab
      Pre-Owned
      $5.40
      Was: $6.0010% off
      or Best Offer
      +$5.50 delivery
      Free returns
      Sponsored
      Top Rated Plus
    • Gymboree Shorts Boys 5 Blue Nautical Sailboat Prep Fit Soft 100% Cotton Preppy
      Gymboree Shorts Boys 5 Blue Nautical Sailboat Prep Fit Soft 100% Cotton Preppy
      Opens in a new window or tab
      Pre-Owned
      $9.99
      or Best Offer
      +$6.99 delivery
      Free returns
      Sponsored
    • Gap Kids Cargo Shorts Boys Size 5 Tan Lightweight Elastic Waist Pockets
      Gap Kids Cargo Shorts Boys Size 5 Tan Lightweight Elastic Waist Pockets
      Opens in a new window or tab
      Pre-Owned
      $9.88
      or Best Offer
      +$5.40 delivery
      Free returns
      Extra 10% off with coupon
      Sponsored
      Top Rated Plus
    • Mini Boden Corduroy Shorts Boys 7Y Youth Orange Bermuda Cut Offs Coastal Beach*
      Mini Boden Corduroy Shorts Boys 7Y Youth Orange Bermuda Cut Offs Coastal Beach*
      Opens in a new window or tab
      Pre-Owned
      $6.82
      Was: $17.0660% off
      or Best Offer
      +$6.49 delivery
      Free returns
      Sponsored
      Top Rated Plus
    • Tommy Hilfiger Cargo Short Youth Size 5 Blue Jean Denim Adjustable Waste Comfort
      Tommy Hilfiger Cargo Short Youth Size 5 Blue Jean Denim Adjustable Waste Comfort
      Opens in a new window or tab
      Pre-Owned
      $19.99
      or Best Offer
      +$14.40 delivery
      Free returns
      Sponsored
    • 2007 GAP KIDS FACTORY Beach Resort Madras Plaid Bermuda Shorts 5 Yrs Olive Navy
      2007 GAP KIDS FACTORY Beach Resort Madras Plaid Bermuda Shorts 5 Yrs Olive Navy
      Opens in a new window or tab
      Pre-Owned
      $5.99
      or Best Offer
      +$6.75 delivery in 2-4 days
      Free returns
      Sponsored
      Top Rated Plus
    • Jumping Beans Boys Sz 7 Striped Pull On Shorts 100% Cotton Preppy
      Jumping Beans Boys Sz 7 Striped Pull On Shorts 100% Cotton Preppy
      Opens in a new window or tab
      Pre-Owned
      $8.00
      or Best Offer
      +$6.00 delivery
      Free returns
      Sponsored
      Top Rated Plus
    • 2007 GYMBOREE BOYS Summer Stock Up Pull-On Cargo Pocket Knit Shorts 5 Yrs Olive
      2007 GYMBOREE BOYS Summer Stock Up Pull-On Cargo Pocket Knit Shorts 5 Yrs Olive
      Opens in a new window or tab
      Pre-Owned
      $7.99
      or Best Offer
      +$6.75 delivery in 2-4 days
      Free returns
      Sponsored
      Top Rated Plus
    • Polo Ralph Lauren Shorts Boys 7 Blue Chambray Pockets Logo Navy PRL #67 Belt
      Polo Ralph Lauren Shorts Boys 7 Blue Chambray Pockets Logo Navy PRL #67 Belt
      Opens in a new window or tab
      Pre-Owned
      $21.99
      or Best Offer
      +$16.55 delivery
      Free returns
      Sponsored
      Top Rated Plus
    • Garanimals Boys Sz 7 Shorts Gray Checkered Pull On 100% Cotton Preppy Summer
      Garanimals Boys Sz 7 Shorts Gray Checkered Pull On 100% Cotton Preppy Summer
      Opens in a new window or tab
      Pre-Owned
      $7.00
      or Best Offer
      +$6.00 delivery
      Free returns
      Sponsored
      Top Rated Plus
    • Tony Hawk Boys Shorts Size 5 Bermuda Grey Plaid 22"Waist 7"Inseam
      Tony Hawk Boys Shorts Size 5 Bermuda Grey Plaid 22"Waist 7"Inseam
      Opens in a new window or tab
      Pre-Owned
      $4.85
      or Best Offer
      +$5.99 delivery
      Free returns
      Sponsored
    • NWT Tucker + Tate Boys Size 7 Pull On Chino Shorts Navy Blue Drawstring
      NWT Tucker + Tate Boys Size 7 Pull On Chino Shorts Navy Blue Drawstring
      Opens in a new window or tab
      Brand New
      $11.99
      Was: $14.9920% off
      Buy It Now
      +$5.99 delivery
      Free returns
      Extra 20% off with coupon
      Sponsored
      Top Rated Plus
    • 2010 GAP KIDS Distressed Cargo Flap Snap Pocket Bermuda Shorts 5T 5 Yrs Khaki
      2010 GAP KIDS Distressed Cargo Flap Snap Pocket Bermuda Shorts 5T 5 Yrs Khaki
      Opens in a new window or tab
      Pre-Owned
      $7.99
      or Best Offer
      +$6.75 delivery in 2-4 days
      Free returns
      Sponsored
      Top Rated Plus
    • Gymboree Toddler Boys Size 5 Multicolor Striped Chino Shorts Casual Preppy
      Gymboree Toddler Boys Size 5 Multicolor Striped Chino Shorts Casual Preppy
      Opens in a new window or tab
      Pre-Owned
      $13.99
      or Best Offer
      +$5.99 delivery
      Free returns
      Sponsored
      Top Rated Plus
    • 2008 GYMBOREE OUTLET BOYS Safari Outback Plaid Bermuda Shorts 5 Yrs Brown
      2008 GYMBOREE OUTLET BOYS Safari Outback Plaid Bermuda Shorts 5 Yrs Brown
      Opens in a new window or tab
      Pre-Owned
      $7.99
      or Best Offer
      +$6.75 delivery in 2-4 days
      Free returns
      Sponsored
      Top Rated Plus
    • 2010 GAP KIDS Durable Goods Cargo Back Pocket Relaxed Bermuda Shorts 5 Yrs Khaki
      2010 GAP KIDS Durable Goods Cargo Back Pocket Relaxed Bermuda Shorts 5 Yrs Khaki
      Opens in a new window or tab
      Pre-Owned
      $7.99
      or Best Offer
      +$6.75 delivery in 2-4 days
      Free returns
      Sponsored
      Top Rated Plus
    • GAP Kids Boy's 7 Regular Plaid Check Patchwork Shorts Adjustable Waist Preppy
      GAP Kids Boy's 7 Regular Plaid Check Patchwork Shorts Adjustable Waist Preppy
      Opens in a new window or tab
      Pre-Owned
      $9.50
      or Best Offer
      +$6.00 delivery
      Free returns
      Sponsored
      Top Rated Plus
    • Boy JK J Khaki Blue& White Seer Sucker Adjustable Waist Preppy Shorts EUC Size 5
      Boy JK J Khaki Blue& White Seer Sucker Adjustable Waist Preppy Shorts EUC Size 5
      Opens in a new window or tab
      Pre-Owned
      $7.75
      or Best Offer
      +$4.65 delivery
      Free returns
      Sponsored
      Top Rated Plus
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