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203 results

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    • PreppyRemove filter
    • Size: 5Remove filter
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    • Properly Tied Mallard Short Preppy Southern Fish Printed Outdoor Green Boys 5
      Properly Tied Mallard Short Preppy Southern Fish Printed Outdoor Green Boys 5
      Opens in a new window or tab
      Pre-Owned
      $24.98
      or Best Offer
      +$8.84 delivery
      Sponsored
    • 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
      $13.59
      Was: $15.9915% off
      or Best Offer
      +$4.84 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
    • 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
    • Properly Tied Youth Small 8 Boys Shorts Grey Elastic Waist Preppy
      Find similar itemsSee all the items on eBay that match this style
      Properly Tied Youth Small 8 Boys Shorts Grey Elastic Waist Preppy
      Opens in a new window or tab
      Brand New
      $20.26
      or Best Offer
      +$8.71 delivery
      Sponsored
    • Adidas athletic shorts Boy Large (14/16)black+red trims/elstc w+drwstrn/pockets
      Adidas athletic shorts Boy Large (14/16)black+red trims/elstc w+drwstrn/pockets
      Opens in a new window or tab
      Pre-Owned
      $5.99
      or Best Offer
      +$4.52 delivery in 2-4 days
      Free returns
      Sponsored
      Top Rated Plus
    • Old Navy Carter’s TCP Jumping Beans Boys Shorts Cargo Khaki Sz 5 Lot Of 5
      Old Navy Carter’s TCP Jumping Beans Boys Shorts Cargo Khaki Sz 5 Lot Of 5
      Opens in a new window or tab
      Pre-Owned
      $25.00
      Buy It Now
      +$7.35 delivery
      Sponsored
    • Janie & Jack Shorts Boys Linen Cotton White Blue Pink Plaid , Sz 4T NWT
      Janie & Jack Shorts Boys Linen Cotton White Blue Pink Plaid , Sz 4T NWT
      Opens in a new window or tab
      Brand New
      $12.00
      0 bids · Time left3d 12h
      or Best Offer
      +$4.71 delivery
      Sponsored
    • Polo Ralph Lauren Shorts 4T Navy Blue Big Pony Casual Flat Front Chino
      Polo Ralph Lauren Shorts 4T Navy Blue Big Pony Casual Flat Front Chino
      Opens in a new window or tab
      Pre-Owned
      $15.50
      or Best Offer
      +$5.80 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
    • 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
      10 watchers
      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
      Buy It Now
      +$5.00 delivery
      Sponsored
    • Tailor Vintage Boys 4 Shorts Striped Lobster Print Blue Preppy Fun Summer
      Tailor Vintage Boys 4 Shorts Striped Lobster Print Blue Preppy Fun Summer
      Opens in a new window or tab
      Pre-Owned
      $22.99
      or Best Offer
      +$4.52 delivery
      Sponsored
    • Janie & Jack Shorts Boys 4 Plaid Zipper Fly Pockets Preppy Casual Cotton Bermuda
      Janie & Jack Shorts Boys 4 Plaid Zipper Fly Pockets Preppy Casual Cotton Bermuda
      Opens in a new window or tab
      Pre-Owned
      $14.44
      Was: $16.9915% off
      or Best Offer
      +$5.75 delivery
      Free returns
      Extra 15% off with coupon
      Sponsored
      Top Rated Plus
    • U.S. Polo ASSN Boys Adjustable Waist Blue Stripe Bermudas Chino Shorts Size 5
      U.S. Polo ASSN Boys Adjustable Waist Blue Stripe Bermudas Chino Shorts Size 5
      Opens in a new window or tab
      Pre-Owned
      $9.99
      or Best Offer
      +$6.98 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
      Extra 40% off with coupon
      Sponsored
      Top Rated Plus
    • 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
      Buy It Now
      Free delivery
      Free returns
      Sponsored
      Top Rated Plus
    • 2pr Boys Sz 5 Plaid Shorts NICE!
      2pr Boys Sz 5 Plaid Shorts NICE!
      Opens in a new window or tab
      Pre-Owned
      $8.00
      0 bids · Time left6d 8h
      $12.00
      Buy It Now
      +$10.00 delivery
      Sponsored
    • Oshkosh Old Navy Sonoma Toughskins Chaps Boys Shorts Cargo Khaki Sz 5 Lot Of 5
      Oshkosh Old Navy Sonoma Toughskins Chaps Boys Shorts Cargo Khaki Sz 5 Lot Of 5
      Opens in a new window or tab
      Pre-Owned
      $30.00
      Buy It Now
      +$7.35 delivery
      Sponsored
    • Gap Kids Boys Size 4 Madras Patchwork Plaid Adjustable Waist Shorts
      Gap Kids Boys Size 4 Madras Patchwork Plaid Adjustable Waist Shorts
      Opens in a new window or tab
      Pre-Owned
      $8.99
      or Best Offer
      +$5.60 delivery
      Free returns
      Sponsored
      Top Rated Plus
    • 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
      Buy It Now
      +$4.84 delivery
      Sponsored
    • Polo Ralph Lauren Seersucker Shorts Stretch Blue/White Classic Fit Size 4 / 4T
      Polo Ralph Lauren Seersucker Shorts Stretch Blue/White Classic Fit Size 4 / 4T
      Opens in a new window or tab
      Brand New
      $22.97
      Buy It Now
      Free delivery in 2-4 days
      5 watchers
      Sponsored
    • POLO RALPH LAUREN BOYS Bermuda Chino Cargo Khaki Shorts 4 Yrs British Tan
      POLO RALPH LAUREN BOYS Bermuda Chino Cargo Khaki Shorts 4 Yrs British Tan
      Opens in a new window or tab
      Pre-Owned
      $12.99
      or Best Offer
      +$8.35 delivery in 2-3 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
    • Boys OLD NAVY BLUE Shorts 18 Cotton XXL Drawstring Active Breathe Pockets
      Boys OLD NAVY BLUE Shorts 18 Cotton XXL Drawstring Active Breathe Pockets
      Opens in a new window or tab
      Pre-Owned
      $6.60
      Was: $6.955% off
      or Best Offer
      +$5.80 delivery
      Sponsored
    • Plaid Shorts 4-5 Boys Gap Golf Pleated Check Colorful Purple Green 90s Size XS
      Plaid Shorts 4-5 Boys Gap Golf Pleated Check Colorful Purple Green 90s Size XS
      Opens in a new window or tab
      Pre-Owned
      $7.03
      0 bids · Time left7h 35m
      $9.99
      Buy It Now
      +$5.80 delivery
      Sponsored
    • 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 2-3 days
      Free returns
      Sponsored
      Top Rated Plus
    • Janie & Jack Boys Yellow Seersucker striped Shorts size 4 Preppy Easter  NWOT
      Janie & Jack Boys Yellow Seersucker striped Shorts size 4 Preppy Easter NWOT
      Opens in a new window or tab
      New (Other)
      $10.00
      0 bids · Time left2d 9h
      $15.00
      Buy It Now
      +$4.33 delivery
      Sponsored
    • NWT CREWCUTS CHINO SHORTS BOYS SIZE 4 YELLOW SPRING EASTER
      NWT CREWCUTS CHINO SHORTS BOYS SIZE 4 YELLOW SPRING EASTER
      Opens in a new window or tab
      Brand New
      $13.39
      Was: $19.9933% off
      or Best Offer
      +$6.95 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
      Extra 40% off with coupon
      Sponsored
      Top Rated Plus
    • The Oaks Apparel Size 5 Boys? Shorts Preppy Aqua Blue Linen Cotton Boutique
      The Oaks Apparel Size 5 Boys? Shorts Preppy Aqua Blue Linen Cotton Boutique
      Opens in a new window or tab
      Pre-Owned
      $14.39
      Was: $15.9910% off
      or Best Offer
      +$6.99 delivery
      Sponsored
    • JANIE and JACK Preppy Stripe Cotton Adjustable Waist Flat Front Shorts I Sz 5
      JANIE and JACK Preppy Stripe Cotton Adjustable Waist Flat Front Shorts I Sz 5
      Opens in a new window or tab
      Pre-Owned
      $16.95
      or Best Offer
      +$6.55 delivery
      Sponsored
    • James & Lottie Play Pima Cotton Preppy Conrad Shorts - Let's Go Fishing Boys 5
      James & Lottie Play Pima Cotton Preppy Conrad Shorts - Let's Go Fishing Boys 5
      Opens in a new window or tab
      Pre-Owned
      $12.80
      Was: $16.0020% off
      or Best Offer
      +$4.33 delivery
      Sponsored
    • Lot Of 2 Oshkosh & Sonoma Shorts  Size 5 ~ 100 % Cotton
      Lot Of 2 Oshkosh & Sonoma Shorts Size 5 ~ 100 % Cotton
      Opens in a new window or tab
      Pre-Owned
      $14.00
      Buy It Now
      Free delivery
      Sponsored
    • 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
      $16.79
      or Best Offer
      +$7.95 delivery
      Sponsored
    • 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 2-3 days
      Free returns
      Sponsored
      Top Rated Plus
    • NWT Polo Ralph Lauren Boys Spa Terry Logo Graphic Athletic Shorts Navy 2/2T
      NWT Polo Ralph Lauren Boys Spa Terry Logo Graphic Athletic Shorts Navy 2/2T
      Opens in a new window or tab
      Brand New
      $28.00
      Buy It Now
      +$6.99 delivery
      Sponsored
    • Tommy Hilfiger Boys 2T-4 Flat Front Sangria Shorts TBSHC11J  Preppy Minimalist
      Tommy Hilfiger Boys 2T-4 Flat Front Sangria Shorts TBSHC11J Preppy Minimalist
      Opens in a new window or tab
      Brand New
      $14.99
      or Best Offer
      +$7.90 delivery
      Free returns
      Extra 10% off with coupon
      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
      Extra 40% off with coupon
      Sponsored
      Top Rated Plus
    • Janie and Jack Boy’s Blue Hawaiian Cotton Shorts Adjustable Waist Size 4
      Janie and Jack Boy’s Blue Hawaiian Cotton Shorts Adjustable Waist Size 4
      Opens in a new window or tab
      Pre-Owned
      $18.88
      or Best Offer
      +$13.10 delivery
      Sponsored
    • GAP Sonoma Garanimals Timberland Boys Shorts Cargo Khaki Sz 4 Lot Of 4
      GAP Sonoma Garanimals Timberland Boys Shorts Cargo Khaki Sz 4 Lot Of 4
      Opens in a new window or tab
      Pre-Owned
      $25.00
      Buy It Now
      +$7.35 delivery
      Sponsored
    • Jordan Shorts Boys Size 2XL Blue White Jumpman Active Athletic Gym Kids
      Jordan Shorts Boys Size 2XL Blue White Jumpman Active Athletic Gym Kids
      Opens in a new window or tab
      Pre-Owned
      $24.95
      or Best Offer
      +$6.95 delivery
      Free returns
      Sponsored
      Top Rated Plus
    • NWT Gap Boys Chambray Shorts Youth Size XXL (14-16) Washwell
      NWT Gap Boys Chambray Shorts Youth Size XXL (14-16) Washwell
      Opens in a new window or tab
      Brand New
      $14.99
      or Best Offer
      +$4.84 delivery
      Free returns
      Sponsored
      Top Rated Plus
    • 2010 GYMBOREE OUTLET California Surfin' Paddle Out Pup Plaid Cargo Shorts 4 Yrs
      2010 GYMBOREE OUTLET California Surfin' Paddle Out Pup Plaid Cargo Shorts 4 Yrs
      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
    • 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 2-3 days
      Free returns
      Sponsored
      Top Rated Plus
    • Polo Ralph Lauren Boys Embroidered Colored Pony Yellow Preppy Shorts Size 5
      Polo Ralph Lauren Boys Embroidered Colored Pony Yellow Preppy Shorts Size 5
      Opens in a new window or tab
      Pre-Owned
      $22.99
      or Best Offer
      +$6.55 delivery
      Sponsored
    • Nike + Polo Ralph Lauren Shorts Boy 4 4T Navy Blue Chino Pocket
      Nike + Polo Ralph Lauren Shorts Boy 4 4T Navy Blue Chino Pocket
      Opens in a new window or tab
      Pre-Owned
      $19.99
      Buy It Now
      Free delivery
      Sponsored
    • 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 2-3 days
      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
      Sponsored
    • Janie and Jack Boys Size 4 Linen Cotton Pink Chino Shorts Easter
      Janie and Jack Boys Size 4 Linen Cotton Pink Chino Shorts Easter
      Opens in a new window or tab
      Pre-Owned
      $8.99
      or Best Offer
      +$5.10 delivery
      Free returns
      Sponsored
      Top Rated Plus
    • Vineyard Vines Boys Size 5 Mint Green Aqua Flat Front Deck Shorts 100% Cotton
      Vineyard Vines Boys Size 5 Mint Green Aqua Flat Front Deck Shorts 100% Cotton
      Opens in a new window or tab
      Pre-Owned
      $9.99
      or Best Offer
      +$4.71 delivery
      Sponsored
    • Janie and Jack Boys khaki Beige Linen Blend Shorts Size 5
      Janie and Jack Boys khaki Beige Linen Blend Shorts Size 5
      Opens in a new window or tab
      Pre-Owned
      $11.99
      or Best Offer
      +$4.71 delivery
      Sponsored
    • J Crew Shorts Boys 26x6 XS Cotton Blue Stripe Drawstring Pockets Preppy Classic
      J Crew Shorts Boys 26x6 XS Cotton Blue Stripe Drawstring Pockets Preppy Classic
      Opens in a new window or tab
      New (Other)
      $20.04
      Was: $22.7712% off
      or Best Offer
      +$6.99 delivery
      Sponsored
    • Vintage Polo Ralph Lauren Boys Khaki Chino Shorts Size 5 Pleated FK010222
      Vintage Polo Ralph Lauren Boys Khaki Chino Shorts Size 5 Pleated FK010222
      Opens in a new window or tab
      Pre-Owned
      $10.96
      Was: $12.8915% off
      or Best Offer
      +$6.40 delivery
      Sponsored
    • Janie and Jack Boys Shorts 4 White Navy Yellow Striped Cotton Preppy Easter Logo
      Janie and Jack Boys Shorts 4 White Navy Yellow Striped Cotton Preppy Easter Logo
      Opens in a new window or tab
      Pre-Owned
      $14.99
      or Best Offer
      +$6.99 delivery
      Free returns
      Sponsored
      Top Rated Plus
    • Janie And Jack Boys Classic Preppy  Navy Blue Sailboat Shorts Size 4
      Janie And Jack Boys Classic Preppy Navy Blue Sailboat Shorts Size 4
      Opens in a new window or tab
      Pre-Owned
      $14.99
      or Best Offer
      +$5.99 delivery
      Sponsored
    • 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
    • Timberland Boys Ripstop Chino Shorts Boys Size 5 Brown
      Timberland Boys Ripstop Chino Shorts Boys Size 5 Brown
      Opens in a new window or tab
      Pre-Owned
      $11.99
      or Best Offer
      +$8.71 delivery
      Sponsored
    • J.Crew Crewcuts BOYS GRAMERCY COTTON DINO SHORT, Size 4, imperial Blue Green
      J.Crew Crewcuts BOYS GRAMERCY COTTON DINO SHORT, Size 4, imperial Blue Green
      Opens in a new window or tab
      Pre-Owned
      $15.00
      Was: $18.9521% off
      or Best Offer
      +$6.55 delivery
      Sponsored
    • Old Navy Boys Shorts Size XXL 18 Gray Blue Sharks Pull On Elastic Drawstring
      Old Navy Boys Shorts Size XXL 18 Gray Blue Sharks Pull On Elastic Drawstring
      Opens in a new window or tab
      Pre-Owned
      $12.34
      Was: $12.995% off
      or Best Offer
      +$4.99 delivery
      Sponsored
    • Vineyard Vines Boys Size 5 Pink Flat Front Deck Shorts 100% Cotton
      Vineyard Vines Boys Size 5 Pink Flat Front Deck Shorts 100% Cotton
      Opens in a new window or tab
      Pre-Owned
      $19.97
      or Best Offer
      +$7.95 delivery
      Sponsored
    • Janie and Jack Soft Taupe Camo Stretch Twill Shorts Boys 4 NEW
      Janie and Jack Soft Taupe Camo Stretch Twill Shorts Boys 4 NEW
      Opens in a new window or tab
      Brand New
      $11.99
      Buy It Now
      +$4.00 delivery
      Sponsored
    • New Polo Ralph Lauren Boys' White Classic Chino Shorts 12
      New Polo Ralph Lauren Boys' White Classic Chino Shorts 12
      Opens in a new window or tab
      New (Other)
      $19.99
      or Best Offer
      +$9.45 delivery
      3 watchers
      Sponsored
    • Tea Collection Blue Plaid Cotton Shorts Boy Size 4
      Tea Collection Blue Plaid Cotton Shorts Boy Size 4
      Opens in a new window or tab
      Pre-Owned
      $11.00
      or Best Offer
      +$5.09 delivery
      Sponsored
    • Chaps Boy’s New Bermuda Shorts 4 Madras Red Blue Plaid Adjustable Waist
      Chaps Boy’s New Bermuda Shorts 4 Madras Red Blue Plaid Adjustable Waist
      Opens in a new window or tab
      Brand New
      $6.29
      Was: $6.9910% off
      or Best Offer
      +$5.85 delivery
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