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- Polo Ralph Lauren Short Boys 8 Khaki Classic Chino Cargo Adjustable Waist PreppyOpens in a new window or tabPre-Owned$18.95Was: $19.955% offor Best Offer+$6.99 deliveryFree returnsExtra 20% off with couponTop Rated Plus
- Polo Ralph Lauren Shorts Youth 8 Green Vintage Plaid Preppy Classic ChinoOpens in a new window or tabPre-Owned$17.99or Best Offer+$6.99 deliveryFree returns
- J Crew Crewcuts Shorts Youth 8 Khaki Cotton Adjustable Waist Chino Shorts PreppyOpens in a new window or tabPre-Owned$12.79Was: $15.9920% offor Best Offer+$5.00 deliveryFree returnsTop Rated Plus
- Mini Boden Shorts Boys Red Casual Drawstring Size 5YOpens in a new window or tabPre-Owned$10.99or Best Offer+$5.00 deliveryFree returnsTop Rated Plus
- Mini Boden Shorts Boy 4Y Blue White Seersucker Stripe Roll-Up Hem Elastic WaistOpens in a new window or tabPre-Owned$8.95or Best Offer+$5.50 deliveryFree returnsTop Rated Plus
- Ralph Lauren Boy'sPull On Shorts Polo 1992 Blue Size M (10-12)Opens in a new window or tabPre-Owned$11.49or Best Offer+$6.55 deliveryFree returnsExtra 15% off with couponTop Rated Plus
- J Crew Crewcuts Boys Classic Khaki Shorts Tan Beige Adjustable Waist Size 8Opens in a new window or tabPre-Owned$15.44or Best Offer+$5.54 deliveryFree returnsExtra 25% off with couponTop Rated Plus
- J. Bailey Boys Seersucker Shorts Blue White Striped Preppy Southern Style Size 8Opens in a new window or tabPre-Owned$22.85or Best Offer+$7.25 deliveryFree returnsTop Rated Plus
- Chaps Boy’s Bermuda Shorts 4 Madras Red Blue Plaid Adjustable Waist NewOpens in a new window or tabBrand New$5.99or Best Offer+$5.85 deliveryFree returnsTop Rated Plus
- Polo Ralph Lauren Boys Size 8 Yellow Flat Front Chino ShortsOpens in a new window or tabPre-Owned$22.98or Best Offer+$5.95 deliveryFree returns
- Crewcuts Shorts Boy’s Size 5 Cotton Adjustable Waist Preppy - Easter - PurpleOpens in a new window or tabPre-Owned$11.00Buy It NowFree deliveryFree returnsTop Rated Plus
- New Crewcuts Boys Classic Pinstripe Gramercy Shorts Blue White Seersucker Size 5Opens in a new window or tabNew (Other)$19.44or Best Offer+$5.54 deliveryFree returnsExtra 25% off with couponTop Rated Plus
- 2010 GAP KIDS Camo Camouflage Cargo Pocket Bermuda Long Shorts 5T 5 Yrs OliveOpens in a new window or tabPre-Owned$9.99or Best Offer+$8.35 delivery in 2-4 daysFree returnsTop Rated Plus
- Gap Kids Boys Shorts Size 8 Gray Checkered Casual Lightweight Summer ChinoOpens in a new window or tabPre-Owned$12.99or Best Offer+$6.95 delivery in 2-4 daysFree returnsExtra 10% off with couponTop Rated Plus
- Janie & Jack Shorts Boys 4 Plaid Zipper Fly Pockets Preppy Casual Cotton BermudaOpens in a new window or tabPre-Owned$16.99or Best Offer+$5.75 deliveryFree returnsExtra 15% off with couponTop Rated Plus
- Gymboree Boys Classic Seersucker Bermuda Shorts Blue White Pinstripe Size 5Opens in a new window or tabPre-Owned$14.44or Best Offer+$5.54 deliveryFree returnsExtra 25% off with couponTop Rated Plus
- POLO RALPH LAUREN BOYS Bermuda Chino Cargo Khaki Shorts 4 Yrs British TanOpens in a new window or tabPre-Owned$12.99or Best Offer+$8.35 delivery in 2-4 daysFree returnsTop Rated Plus
- 2010 OLD NAVY BOYS Mixed Plaid Madras Patchwork Bermuda Trouser Shorts 5 YrsOpens in a new window or tabPre-Owned$7.99or Best Offer+$6.75 delivery in 2-4 daysFree returnsTop Rated Plus
- David Brooks Shorts Boys 8 Whales Bermuda Straight Cotton Sailing Preppy DockOpens in a new window or tabPre-Owned$9.90Was: $18.0045% offor Best Offer+$5.80 deliveryFree returnsTop Rated Plus
- New Mayoral Boys Tailored Dress Shorts Gray Black Microprint Size 5 (110cm)Opens in a new window or tabBrand New$24.44or Best Offer+$5.54 deliveryFree returnsExtra 25% off with couponTop Rated Plus
- Boys Elastic Waist Drawstring Cotton Blend Army Camouflage Kids Cargo ShortsOpens in a new window or tabBrand New$26.74Buy It NowFree delivery in 2-4 daysFree returnsTop Rated Plus
- Gap Kids Boys Size 4 Madras Patchwork Plaid Adjustable Waist ShortsOpens in a new window or tabPre-Owned$8.99or Best Offer+$5.60 deliveryFree returnsTop Rated Plus
- Old Navy Pull On Linen Blend Shorts Boys Size Medium 8 Tan Drawstring WaistOpens in a new window or tabPre-Owned$5.60Was: $7.0020% offor Best Offer+$4.98 deliveryFree returnsTop Rated Plus
- 2011 GYMBOREE BOYS Golf Pro Tee Off Patchwork Mixed Plaid Check Shorts 5T 5 YrsOpens in a new window or tabPre-Owned$7.99or Best Offer+$6.75 delivery in 2-4 daysFree returnsTop Rated Plus
- JANIE & JACK Boys Patchwork Shorts 5T Toddler Size 5 ~Navy Blue PlaidOpens in a new window or tabPre-Owned$15.00Buy It Now+$5.50 deliveryFree returns
- 2009 GYMBOREE Spring Car Classic Stripe Seersucker Patchwork Cargo Shorts 5 YrsOpens in a new window or tabPre-Owned$12.99or Best Offer+$6.75 delivery in 2-3 daysFree returnsTop Rated Plus
- Adidas athletic shorts Boy Large (14/16)black+red trims/elstc w+drwstrn/pocketsOpens in a new window or tabPre-Owned$5.99or Best Offer+$4.52 delivery in 2-4 daysFree returnsTop Rated Plus
- Old Navy Boys Patchwork Shorts Bermuda Madras Plaid Size 8Opens in a new window or tabPre-Owned$17.98or Best Offer+$5.95 deliveryFree returns
- NWT CREWCUTS CHINO SHORTS BOYS SIZE 4 YELLOW SPRING EASTEROpens in a new window or tabBrand New$19.99or Best Offer+$6.95 deliveryFree returns
- Brooks Brothers Fleece Shorts Boys 4 Beige Khaki Outdoors Hiking Preppy SchoolOpens in a new window or tabPre-Owned$19.99or Best Offer+$10.99 deliveryFree returnsTop Rated Plus
- Cat & Jack Boys Shorts Summer Pants Size 8 Gray Chino Active Uniform PreppyOpens in a new window or tabPre-Owned$12.99or Best Offer+$7.99 deliveryFree returnsExtra 8% off with couponTop Rated Plus
- Polo Ralph Lauren Shorts Boy Youth 8 Chino Cargo Preppy Baggy Loose Khaki BeigeOpens in a new window or tabPre-Owned$14.97Buy It Now+$6.99 deliveryFree returnsTop Rated Plus
- 2010 GAP KIDS Embroidered Pirate Skull Crossbones Bermuda Shorts 5 Yrs KhakiOpens in a new window or tabPre-Owned$9.99or Best Offer+$6.75 delivery in 2-4 daysFree returnsTop Rated Plus
- TCP THE CHILDREN'S PLACE Nautical Plaid Patchwork Pocket Lined Shorts 4T 4 YrsOpens in a new window or tabPre-Owned$7.99or Best Offer+$6.75 delivery in 2-4 daysFree returnsTop Rated Plus
- Janie and Jack Boys Size 4 Linen Cotton Pink Chino Shorts EasterOpens in a new window or tabPre-Owned$8.99or Best Offer+$5.10 deliveryFree returnsTop Rated Plus
- 2011 GYMBOREE Surf Rocks Drawstring Pull-On Plaid Pocket Long Shorts 5T 5 YrsOpens in a new window or tabPre-Owned$9.99or Best Offer+$6.75 delivery in 2-4 daysFree returnsTop Rated Plus
- VTG 2004 GAP KIDS Durable Goods Cargo Pocket Bermuda Shorts 5T 5 Yrs Moss GreenOpens in a new window or tabPre-Owned$9.99or Best Offer+$8.35 delivery in 2-4 daysFree returnsTop Rated Plus
- 2010 GYMBOREE OUTLET California Surfin' Paddle Out Pup Plaid Cargo Shorts 4 YrsOpens in a new window or tabPre-Owned$6.99or Best Offer+$6.75 delivery in 2-4 daysFree returnsTop Rated Plus
- Childrens Place Blue Brown Shorts Boys 8 School Uniform Adjustable Waist lot 4Opens in a new window or tabPre-Owned$14.26Was: $23.7740% offor Best Offer+$9.86 deliveryFree returnsTop Rated Plus
- Tommy Hilfiger Boys 2T-4 Flat Front Sangria Shorts TBSHC11J Preppy MinimalistOpens in a new window or tabBrand New$14.99or Best Offer+$7.90 deliveryFree returnsExtra 10% off with couponTop Rated Plus
- 2007 GAP KIDS FACTORY Beach Resort Madras Plaid Bermuda Shorts 5 Yrs Olive NavyOpens in a new window or tabPre-Owned$5.99or Best Offer+$6.75 delivery in 2-4 daysFree returnsTop Rated Plus
- 2013 OLD NAVY BOYS Classic Plaid Bermuda Summer Shorts 5T 5 Yrs Blue Red MultiOpens in a new window or tabPre-Owned$7.99or Best Offer+$6.75 delivery in 2-4 daysFree returnsTop Rated Plus
- Vintage Youth Izod Lacoste Pocket Shorts Boys Size 4 Blue PreppyOpens in a new window or tabPre-Owned$2.80Was: $13.9980% offBuy It Now+$7.00 deliveryFree returnsTop Rated Plus
- crewcuts Kids Shorts Plaid Pattern Pull On Drawstring Preppy Patchwork Size 5Opens in a new window or tabPre-Owned$19.00or Best Offer+$6.89 deliveryFree returnsTop Rated Plus
- Janie and Jack Boys Shorts 4 White Navy Yellow Striped Cotton Preppy Easter LogoOpens in a new window or tabPre-Owned$14.99or Best Offer+$6.99 deliveryFree returnsTop Rated Plus
- Tommy Hilfiger Cargo Short Youth Size 5 Blue Jean Denim Adjustable Waste ComfortOpens in a new window or tabPre-Owned$19.99or Best Offer+$14.40 deliveryFree returns
- POLO RALPH LAUREN BOY Preppy Pleated Bermuda Chino Summer Shorts 4 Yrs KhakiOpens in a new window or tabPre-Owned$9.99or Best Offer+$8.35 delivery in 2-4 daysFree returnsTop Rated Plus
- The Children's Place Boys Shorts Multicolor Patches 8 CottonOpens in a new window or tabPre-Owned$12.99or Best Offer+$6.55 deliveryFree returnsTop Rated Plus
- 2010 GAP KIDS FACTORY Beach Resort Madras Plaid Bermuda Shorts 5 Yrs Light BlueOpens in a new window or tabPre-Owned$5.99or Best Offer+$6.75 delivery in 2-4 daysFree returnsTop Rated Plus
- Boys 8 Ruff Hewn Khaki Shorts Tan Casual Youth Euc Adjustable Waist ChinosOpens in a new window or tabPre-Owned$4.85Was: $5.7015% offor Best Offer+$6.55 deliveryFree returnsExtra 5% off with couponTop Rated Plus
- Lee Boys Casual Cargo Khaki Shorts Size 4T 20"Waist 6"InseamOpens in a new window or tabPre-Owned$1.76Was: $5.8570% offor Best Offer+$5.99 deliveryFree returns
- Tony Hawk Boys Shorts Size 5 Bermuda Grey Plaid 22"Waist 7"InseamOpens in a new window or tabPre-Owned$1.45Was: $4.8570% offor Best Offer+$5.99 deliveryFree returns
- Childrens Place Shorts Boys Size 8 Plaid Blue, Teal, Navy Preppy Academia SchoolOpens in a new window or tabPre-Owned$4.99or Best Offer+$4.99 deliveryFree returnsTop Rated Plus
- 2010 GYMBOREE BOYS Celebrate Spring Easter Gingham Cargo Shorts 4T 4 Yrs BrownOpens in a new window or tabPre-Owned$12.99or Best Offer+$6.75 delivery in 2-3 daysFree returnsTop Rated Plus
- Gymboree Toddler Boys Size 5 Multicolor Striped Chino Shorts Casual PreppyOpens in a new window or tabPre-Owned$13.99or Best Offer+$5.99 deliveryFree returnsTop Rated Plus
- Nautica Boy School Uniform Performance Stretch Easy Care Short Lowell KhakiOpens in a new window or tabBrand New$14.40Buy It Now+$5.62 deliveryFree returnsSave up to 20% when you buy more
- Gap Kid Boy Pull On Elastic Waistband Front Back Pockets Soft Twill Navy Sz 8 L5Opens in a new window or tabBrand New$6.99Buy It Now+$5.99 deliveryFree returns
- 2007 GYMBOREE OUTLET BOYS Resort Getaway Dapper Plaid Bermuda Shorts 5 Yrs BlueOpens in a new window or tabPre-Owned$6.99or Best Offer+$6.75 delivery in 2-4 daysFree returnsTop Rated Plus
- 2011 GYMBOREE BOYS Deep Sea Adventure Dude Plaid Bermuda Summer Shorts 4T 4 YrsOpens in a new window or tabPre-Owned$7.99or Best Offer+$6.75 delivery in 2-4 daysFree returnsTop Rated Plus
- Gap Kids Boys Size 8 Blue Star Print Chino ShortsOpens in a new window or tabPre-Owned$13.99or Best Offer+$5.99 deliveryFree returnsTop Rated Plus
- 2007 GYMBOREE BOYS Summer Stock Up Pull-On Cargo Pocket Knit Shorts 5 Yrs OliveOpens in a new window or tabPre-Owned$7.99or Best Offer+$6.75 delivery in 2-4 daysFree returnsTop Rated Plus
- Gymboree Shorts Boys 5 Blue Nautical Sailboat Prep Fit Soft 100% Cotton PreppyOpens in a new window or tabPre-Owned$9.99or Best Offer+$5.99 deliveryFree returns
- Cambridge Classics Boys Shorts Size 4 Black School Preppy Chino Flat FrontOpens in a new window or tabPre-Owned$4.48Was: $8.9550% offor Best Offer+$5.99 delivery in 2-4 daysFree returnsTop Rated Plus
- 2010 GAP KIDS Durable Goods Cargo Back Pocket Relaxed Bermuda Shorts 5 Yrs KhakiOpens in a new window or tabPre-Owned$7.99or Best Offer+$6.75 delivery in 2-4 daysFree returnsTop Rated Plus
- 2010 GAP KIDS Distressed Cargo Flap Snap Pocket Bermuda Shorts 5T 5 Yrs KhakiOpens in a new window or tabPre-Owned$7.99or Best Offer+$6.75 delivery in 2-4 daysFree returnsTop Rated Plus
- Boy JK J Khaki Blue& White Seer Sucker Adjustable Waist Preppy Shorts EUC Size 5Opens in a new window or tabPre-Owned$7.75or Best Offer+$4.65 deliveryFree returnsTop Rated Plus
- Boys Plaid Shorts J. Khaki Green Black Chino Size 8 Adjustable Zip PreppyOpens in a new window or tabPre-Owned$11.99or Best Offer+$4.84 deliveryFree returnsTop Rated Plus
- 2008 GYMBOREE OUTLET BOYS Safari Outback Plaid Bermuda Shorts 5 Yrs BrownOpens in a new window or tabPre-Owned$7.99or Best Offer+$6.75 delivery in 2-4 daysFree returnsTop Rated Plus
- Nautica Lowell Khaki Boys' School Uniform Elastic Waistband Jogger Shorts, US 4Opens in a new window or tabBrand New$16.00Buy It Now+$5.62 deliveryFree returnsLast one
- Gap Kid Boy Pull On Elastic Waistband Front Back Pocket Soft Twill Green Sz 8 L5Opens in a new window or tabBrand New$6.99Buy It Now+$5.99 deliveryFree returns
- Gymboree Boy's Shorts Size 4 Gray Green Plaid 100% CottonOpens in a new window or tabPre-Owned$7.46Was: $12.4440% offor Best OfferFree deliveryFree returnsTop Rated Plus
- Adidas Shorts Boys 14/16 Linear Logo Black Elastic Waistband Activewear StretchOpens in a new window or tabPre-Owned$18.00or Best Offer+$7.99 deliveryFree returns
- Faded Glory Shorts Youth Boy's White Plaid Adjustable Waist Size 8 PreppyOpens in a new window or tabPre-Owned$4.50or Best Offer+$7.95 deliveryFree returns
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