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- 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
- Nike Golf Shorts Youth Boys Size XL Dri Fit Gray Stretch 10.5” Inseam Flat FrontOpens in a new window or tabPre-Owned$14.99or Best Offer+$6.99 deliveryFree returnsTop Rated Plus
- Vineyard Vines Shorts Boy 8 Youth Blue Performance Golf Chino Stretch Flat FrontOpens in a new window or tabPre-Owned$15.99Was: $19.9920% offor Best Offer+$6.99 deliveryFree returnsTop Rated Plus
- Polo Ralph Lauren Shorts Boys Size 8 Flat Front Cotton Green Chino Casual PreppyOpens in a new window or tabPre-Owned$19.99or Best Offer+$5.99 deliveryFree returnsExtra 15% off with couponTop Rated Plus
- Travis Mathew Shorts Boys Size 8 Blue Golf Preppy Sports Casual OutdoorOpens in a new window or tabPre-Owned$10.77Was: $17.9540% offor Best Offer+$5.95 deliveryFree returnsExtra 20% off with couponTop Rated Plus
- Gap Boy's Elastic Waistband Front & Back Pockets Stretch Soft Twill ShortsOpens in a new window or tabBrand New$14.99List price: $30.9952% offBuy It NowFree deliveryFree returnsSave up to 30% when you buy moreTop Rated Plus
- Under Armour Shorts Boys Xl Bermuda Shorts Blue PolyesterOpens in a new window or tabBrand New$7.00Was: $34.9980% offor Best Offer+$6.99 deliveryFree returns30% off 2+ with couponTop Rated Plus
- Polo Ralph Lauren Shorts Boys Youth XL 18-20 Blue 2012 Olympics Sweatshorts LogoOpens in a new window or tabPre-Owned$14.99or Best Offer+$6.99 deliveryFree returnsTop Rated Plus
- Cat & Jack Boys Shorts Summer Pants Size 8 Gray Chino Active Uniform PreppyOpens in a new window or tabPre-Owned$5.59Was: $12.9957% offor Best Offer+$7.99 deliveryFree returnsExtra 15% off with couponTop Rated Plus
- Nike Shorts Boys XL Golf Flex Performance Chinos Long Casual Youth Stretch PrepOpens in a new window or tabPre-Owned$23.99Buy It Now+$6.89 deliveryFree returnsTop Rated Plus
- Crewcuts Shorts Boys Extra Large Blue Striped Causal Drawstring Everyday BasicOpens in a new window or tabPre-Owned$11.99Was: $14.9920% offor Best Offer+$6.99 deliveryFree returns20% off 3+ with couponTop Rated Plus
- Polo Ralph Lauren Shorts Kids Boys Small 8 Navy Blue Fleece Drawstring PreppyOpens in a new window or tabPre-Owned$18.00or Best Offer+$7.25 deliveryFree returnsTop Rated Plus
- Nike Golf Shorts Boys XL Gray Red Windowpane Dri Fit Chinos Adjustable WaistOpens in a new window or tabPre-Owned$12.63Was: $15.9921% offor Best Offer+$5.45 deliveryFree returnsExtra 10% off with couponTop Rated Plus
- Ralph Lauren Polo Shorts Boys Extra Large Size 16 Brown Chino Preppy Boys KidsOpens in a new window or tabPre-Owned$16.88or Best Offer+$6.99 deliveryFree returnsExtra 15% off with couponTop Rated Plus
- J Crew Crewcuts Boys Classic Chino Bermuda Shorts Blue Adjustable Waist Size 7Opens in a new window or tabPre-Owned$15.44or Best Offer+$5.54 deliveryFree returnsTop Rated Plus
- Polo Ralph Lauren Shorts Boys 7 Colorful Chino Preppy Youth School PlaidOpens in a new window or tabPre-Owned$14.75or Best Offer+$6.40 deliveryFree returns
- Childrens Place Shorts Boys Size 8 Plaid Blue, Teal, Navy Preppy Academia SchoolOpens in a new window or tabPre-Owned$4.97or Best Offer+$4.99 deliveryFree returnsTop Rated Plus
- NWT Gap Boys Chambray Shorts Youth Size XL (12) Washwell Elastic Waist PocketsOpens in a new window or tabBrand New$14.99or Best Offer+$4.84 deliveryFree returnsTop Rated Plus
- Nike Golf Shorts Boys XL Tan Khaki Flat Front Dri-FIT Stretch Junior YouthOpens in a new window or tabPre-Owned$13.99or Best Offer+$5.99 deliveryFree returnsTop Rated Plus
- Crewcuts Shorts Boys Size 7 Green Fish Pattern Playful Coastal Preppy CasualOpens in a new window or tabPre-Owned$12.67Was: $16.8925% offor Best Offer+$7.99 deliveryFree returnsTop Rated Plus
- J Crew Crewcuts Shorts Youth 8 Khaki Cotton Adjustable Waist Chino Shorts PreppyOpens in a new window or tabPre-Owned$11.19Was: $13.9920% offor Best Offer+$5.00 deliveryFree returnsTop Rated Plus
- HAWK Gray Checkered Preppy Shorts Youth Boys Size 7Opens in a new window or tabPre-Owned$5.10Was: $6.0015% offor Best Offer+$5.50 deliveryFree returnsTop Rated Plus
- Polo Ralph Lauren Boys Striped Drawstring Shorts Size XL 18-20 Cotton PreppyOpens in a new window or tabPre-Owned$18.90Was: $21.0010% offor Best Offer+$5.95 deliveryFree returns
- Jumping Beans Boys Sz 7 Striped Pull On Shorts 100% Cotton PreppyOpens in a new window or tabPre-Owned$8.00or Best Offer+$6.00 deliveryFree returnsExtra 5% off with couponTop Rated Plus
- Children’s Place Shorts Boys Size 8 Plaid Red Blue White School Academia PreppyOpens in a new window or tabPre-Owned$4.97or Best Offer+$5.99 deliveryFree returnsTop Rated Plus
- Chaps Boy’s Bermuda Shorts 4 New Madras Red Blue Plaid Adjustable WaistOpens in a new window or tabBrand New$7.99or Best Offer+$5.85 deliveryFree returnsTop Rated Plus
- Polo Ralph Lauren Classic Chino Shorts Youth 7 Navy Blue Belted Preppy KidsOpens in a new window or tabPre-Owned$15.95Buy It Now+$5.50 deliveryFree returnsTop Rated Plus
- Under Armour Shorts Boys Extra Large Khaki Lightweight Performance Golf ChinoOpens in a new window or tabPre-Owned$15.77or Best Offer+$5.95 deliveryFree returnsExtra 10% off with couponTop Rated Plus
- Crew Cuts Boys 8 Shorts 100% Linen Light Blue Pockets CrewcutsOpens in a new window or tabPre-Owned$17.99Buy It Now+$5.85 deliveryFree returns
- Levis Shorts Boys Extra Large Black Slim Fit Chino Drawstring Stretch PreppyOpens in a new window or tabPre-Owned$26.99Was: $29.9910% offor Best Offer+$9.95 deliveryFree returnsTop Rated Plus
- Carhartt Shorts Boys Size 8 Reg Ripstop Cargo 8" Inseam Brown Kids Youth PocketsOpens in a new window or tabPre-Owned$19.99or Best Offer+$5.95 deliveryFree returnsExtra 15% off with couponTop Rated Plus
- Polo Ralph Lauren Shorts Boys 7 Blue Straight Leg Preppy Casual Pockets CottonOpens in a new window or tabPre-Owned$20.00or Best Offer+$6.50 deliveryFree returnsTop Rated Plus
- Gap Kid Boy Pull On Elastic Waistband Front Back Pocket Soft Twill Green XL L5Opens in a new window or tabBrand New$6.99Buy It Now+$5.99 deliveryFree returnsLast one
- Garanimals Boys Sz 7 Shorts Gray Checkered Pull On 100% Cotton Preppy SummerOpens in a new window or tabPre-Owned$7.00or Best Offer+$6.00 deliveryFree returnsExtra 5% off with couponTop Rated Plus
- Here+There Shorts Youth Boys EU158 28" Waist XL Plaid Skate Surf Zip PocketsOpens in a new window or tabPre-Owned$15.00or Best Offer+$6.00 deliveryFree returnsTop Rated Plus
- Boys 8 Ruff Hewn Khaki Shorts Tan Casual Youth Euc Adjustable Waist ChinosOpens in a new window or tabPre-Owned$5.13Was: $5.7010% offor Best Offer+$6.55 deliveryFree returnsTop Rated Plus
- Nautica Cargo Shorts Boys 7 Beige Khaki Shorts Adjustable Waist Summer ReadyOpens in a new window or tabPre-Owned$10.00or Best Offer+$6.99 deliveryFree returnsTop Rated Plus
- Cat & Jack Boys Sz 8 Adjustable Waist Classic Khaki Brown Flat School ShortsOpens in a new window or tabPre-Owned$4.00Buy It Now+$8.19 deliveryFree returns
- Volcom Fruckin V4S Hybrid Shorts Boys Sage Green Surf Turf Flat Front 9" Sz 8Opens in a new window or tabBrand New$19.99or Best Offer+$5.00 deliveryFree returnsTop Rated Plus
- Tommy Hilfiger Shorts Mens XL 20 Blue All Over Print Drawstring BermudaOpens in a new window or tabPre-Owned$5.59Was: $7.9930% offor Best Offer+$6.99 deliveryFree returnsExtra 10% off with couponTop 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
- Childrens Place Blue Brown Shorts Boys 8 School Uniform Adjustable Waist lot 4Opens in a new window or tabPre-Owned$16.64Was: $23.7730% offor Best Offer+$9.86 deliveryFree returnsExtra 25% off with couponTop Rated Plus
- Mini Boden Corduroy Shorts Boys 7Y Youth Orange Bermuda Cut Offs Coastal Beach*Opens in a new window or tabPre-Owned$8.53Was: $17.0650% offor Best Offer+$6.49 deliveryFree returnsTop Rated Plus
- PENGUIN nwt NEW~edium Brown Canvas Casual Shorts~Boy's Size ~8Y~Drawstring~8~Opens in a new window or tabBrand New$18.95or Best Offer+$4.00 deliveryFree returnsTop Rated Plus
- Gap Kids Boys Shorts Size 8 Gray Checkered Casual Lightweight Summer ChinoOpens in a new window or tabPre-Owned$6.49Was: $12.9950% offor Best Offer+$6.95 deliveryFree returnsExtra 10% off with couponTop Rated Plus
- NWT Tucker + Tate Boys Size 7 Pull On Chino Shorts Navy Blue DrawstringOpens in a new window or tabBrand New$11.99Was: $14.9920% offBuy It Now+$5.99 deliveryFree returnsExtra 20% off with couponTop Rated Plus
- Polo Ralph Lauren Boys White Blue Embroidered Preppie Chino Shorts Size 8 NWTOpens in a new window or tabBrand New$38.25Was: $45.0015% offBuy It Now+$4.84 deliveryFree returns
- 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
- GAP Kids Boy's 7 Regular Plaid Check Patchwork Shorts Adjustable Waist PreppyOpens in a new window or tabPre-Owned$9.50or Best Offer+$6.00 deliveryFree 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
- Nike Shorts Boys XL Charcoal Gray Woven Elastic Waist Drawstring Cotton NylonOpens in a new window or tabPre-Owned$17.43Was: $23.2425% offor Best Offer+$6.84 deliveryFree returnsTop Rated Plus
- J.Crew Crewcuts Sz 8 Slim Seersucker Adj Waist Shorts Blue White 5 Pocket EUCOpens in a new window or tabPre-Owned$15.99Buy It Now+$5.95 deliveryFree returnsTop 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
- 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
- REI Shorts Boys Extra Large Gray Cargo Lightweight Hiking OutdoorOpens in a new window or tabPre-Owned$12.95or Best Offer+$5.99 delivery in 2-4 daysFree returns
- Boys Elastic Waist Drawstring Cotton Blend Army Camouflage Kids Cargo ShortsOpens in a new window or tabBrand New$26.74Buy It NowFree deliveryFree returnsSave up to 20% when you buy moreTop Rated Plus
- 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
- Under Armour Shorts Boys XL Beige Flat Front Golf Chino Loose Fit Preppy CasualOpens in a new window or tabPre-Owned$19.96or Best Offer+$6.99 deliveryFree returnsTop Rated Plus
- Lee Boys Size XL Khaki Cargo Shorts Beige Relaxed Fit NewOpens in a new window or tabBrand New$16.90or Best OfferFree deliveryFree returnsTop Rated Plus
- 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
