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- Boys Tony Hawk Shorts Green Plaid Size 18 Skater PreppyOpens in a new window or tabPre-Owned$16.99or Best OfferFree delivery
- J.Crew Boys Crewcuts Active Shorts Size 8 Brown Tan Outdoors Training PreppyOpens in a new window or tabPre-Owned$19.99Buy It Now+$4.84 delivery
- Polo Ralph Lauren Chino Shorts Boys Sz 5 NavyOpens in a new window or tabPre-Owned$14.99or Best Offer+$4.99 delivery
- Brooks Brothers Shorts Youth Boy 18 Patchwork Plaid Cotton 28x10 Preppy AcademiaOpens in a new window or tabPre-Owned$19.99Buy It Now+$5.26 delivery
- James & Lottie Play Preppy Conrad Shorts - Let's Go Fishing Size 5Opens in a new window or tabPre-Owned$20.00or Best Offer+$4.33 delivery
- Gymboree boys 8 madras preppy plaid Bermuda shorts blue yellow summer brightOpens in a new window or tabPre-Owned$20.00or Best Offer+$7.35 delivery
- 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
- Wonder Nation Boys Sz 18 Shorts Blue Flat Front Chino Stretch Adjustable PreppyOpens in a new window or tabPre-Owned$7.00or Best Offer+$7.00 deliveryFree returnsExtra 5% off with couponTop Rated Plus
- Crewcuts Blue Chino Khaki Shorts Preppy 7" Inseam - Size Boy's 8Opens in a new window or tabPre-Owned$9.99or Best Offer+$6.55 delivery
- Hurley Nike Dri-Fit Mens Boys 18 Gray Shorts Golf Casual Spring Summer PreppyOpens in a new window or tabPre-Owned$10.00or Best Offer+$4.84 delivery
- Bundle (4) Boys Shorts Ralph Lauren Carters Dogs Preppy Khaki Navy White 5TOpens in a new window or tabPre-Owned$53.00Buy It Now+$17.55 delivery
- 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
- POLO Ralph Lauren Cargo Boys Shorts Size 18 Khaki Tan Straight Leg Cotton ChinoOpens in a new window or tabPre-Owned$15.00or Best Offer+$12.71 delivery
- Lands End Shorts Boys 20H Red Plaid Flat Front Adjustable Waist Elastic PreppyOpens in a new window or tabPre-Owned$9.99or Best Offer+$6.99 deliveryFree returns
- Vineyard Vines Shorts Boys Size 18 Blue Chino Whales Casual Preppy StretchOpens in a new window or tabPre-Owned$9.50Was: $18.9950% offor Best Offer+$5.95 deliveryFree returnsTop Rated Plus
- Polo Ralph Lauren Prepster Patchwork Madras Shorts Little Boys Size 5 Preppy NWTOpens in a new window or tabBrand New$25.00or Best Offer+$5.00 delivery
- Gap Kids Boys Pull On Elastic Waistband Front & Back Pockets Stretch ShortsOpens in a new window or tabBrand New$12.00or Best Offer+$6.20 delivery
- Hanna Andersson Baggies Striped Terry Shorts Size 110 5 Green White 100% CottonOpens in a new window or tabPre-Owned$18.00Was: $20.0010% offor Best Offer+$4.84 delivery
- POLO RALPH LAUREN Boys Belted Bermuda Shorts Size 18 Navy Blue NEW Chino UniformOpens in a new window or tabBrand New$15.00or Best Offer+$5.95 deliveryExtra 15% off with coupon
- Polo Ralph Lauren Chino Shorts Boys 20 BlueOpens in a new window or tabPre-Owned$9.00or Best Offer+$5.95 deliveryFree returnsTop Rated Plus
- Baby Gap Boys 5 Years Chambray Blue Pink & White Striped Preppy ShortsOpens in a new window or tabPre-Owned$1.99Buy It Now+$6.55 delivery
- Polo Ralph Lauren Boys 5 Seersucker Shorts Blue White Adj Waist EUCOpens in a new window or tabPre-Owned$17.00Buy It Now+$5.00 delivery
- Chubbies Shorts Kids 5 Pink Pull on Alligator Preppy Modern Summer DrawstringOpens in a new window or tabNew (Other)$25.00or Best Offer+$5.62 delivery
- NWT Gap Kids Navy Blue Cargo Shorts Adjustable Tab Waist Size 8Opens in a new window or tabBrand New$15.99or Best Offer+$6.55 delivery
- Tommy Hilfiger Boys Sz 20 Shorts Blue Flat Front Chino 100% Cotton Preppy SummerOpens in a new window or tabPre-Owned$17.00or Best Offer+$7.00 deliveryFree returnsExtra 5% off with couponTop Rated Plus
- Strasburg Boys Shorts Size 5 Solid White Dress Preppy NEWOpens in a new window or tabBrand New$20.00or Best Offer+$7.31 delivery
- 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
- NWT Gap Boy's Elastic Waistband Stretch Soft Twill Shorts Size M (8) BlueOpens in a new window or tabBrand New$19.99or Best OfferFree delivery
- Land's End Boy's Short Bermuda Flat Front Red Pink Salmon Summer Preppy Size 20Opens in a new window or tabPre-Owned$14.67Was: $16.2510% offor Best Offer+$5.80 deliveryFree returnsTop 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
- Polo Ralph Lauren Chino Shorts Youth Boys Size 20 Fits 30x11 Beige Preppy CasualOpens in a new window or tabPre-Owned$23.64Was: $24.885% offor Best Offer+$5.95 deliveryFree returnsTop Rated Plus
- Children's Place Blue White Stripe Palm Tree Boys Chino Shorts Size 8 PreppyOpens in a new window or tabPre-Owned$12.99or Best Offer+$4.84 delivery
- Sz 18 Husky Boys Shorts, Khaki Chino 10" Inseam Flat Front NewOpens in a new window or tabNew (Other)$10.99or Best Offer+$5.80 delivery
- Tommy Hilfiger Boys Size 20 Husky Navy Blue Shorts Uniform PreppyOpens in a new window or tabPre-Owned$13.00Buy It Now+$5.00 delivery
- Ralph Lauren Polo Madras Plaid Patchwork Preppy Bermuda Shorts Boys Size 18Opens in a new window or tabPre-Owned$15.00or Best Offer+$5.80 delivery
- Vineyard Vines by Shep & Ian Boys Coral Shorts Size 18Opens in a new window or tabPre-Owned$9.95or Best Offer+$6.55 delivery
- 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
- NWT BELLA BLISS Boys Sz 8 Blue Wide Oxford Striped Play Shorts PreppyOpens in a new window or tabBrand New$15.99or Best Offer+$6.00 delivery
- Children's Place Burnt Orange/Red Boys Chino Shorts Size 8 Stylish PreppyOpens in a new window or tabPre-Owned$12.99or Best Offer+$4.84 delivery
- Children’s Place Green Shorts Boys Size 5 Chinos Elastic Cotton Preppy Y2KOpens in a new window or tabPre-Owned$4.75or Best Offer+$6.40 delivery
- Polo Ralph Lauren Pink Preppy Oxford Bermuda Shorts Young Men's 20 30 WaistOpens in a new window or tabBrand New$50.60Buy It Now+$7.35 delivery
- Crewcuts Green Embroidered Navy Scorpians Shorts Size 5 Boys Adjustable waistOpens in a new window or tabPre-Owned$13.20Was: $15.0012% offor Best Offer+$4.75 delivery
- White Blue Striped Preppy Shorts Boy’s 8 Adjustable Waist Lightweight Fall trendOpens in a new window or tabPre-Owned$15.00or Best Offer+$9.45 delivery
- Vintage Red Gap Kids Cargo Shorts size 8 Spring 2004 Line Y2K PreppyOpens in a new window or tabPre-Owned$15.00or Best Offer+$4.54 delivery
- The Childrens Place 4T Bugs Novelty Shorts Orange Pullon Elastic Waistband NEWOpens in a new window or tabBrand New$12.00Buy It Now+$4.35 delivery
- Boys Ralph Lauren Classic Polo Chino Shorts 18 29 in waist White Navy Ponys GolfOpens in a new window or tabPre-Owned$21.11Was: $23.9912% offor Best Offer+$5.25 delivery
- Polo Ralph Lauren Boy’s Pink Preppy Bermuda Long Shorts 18Opens in a new window or tabPre-Owned$22.00or Best Offer+$8.90 delivery
- White Blue Striped Preppy Shorts Boy’s 8 Adjustable Waist Lightweight Fall trendOpens in a new window or tabPre-Owned$20.00or Best Offer+$9.45 delivery
- Lands End Kids S Small 8 Rust Khaki Striped Shorts Dress Preppy Drawstring ChinoOpens in a new window or tabPre-Owned$14.99or Best Offer+$6.55 delivery
- NWT Tailor Vintage Boys Pineapple Bermuda Shorts 8 ResortwearOpens in a new window or tabBrand New$22.99or Best Offer+$5.00 delivery
- NWT GAP KIDS MISSION TAN Navy Blue Dress SHORTS Size 5 6 Calvin Klein Lot of 3Opens in a new window or tabBrand New$39.00Buy It Now+$10.99 delivery
- Zara boys checkered shorts with rope tie and pockets. Preppy shorts sz 8 128cmOpens in a new window or tabPre-Owned$16.00or Best Offer+$14.25 delivery
