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- Little Britches Boy's Ole Miss Gingham Shorts Size 3T Preppy Ole Miss ShortsOpens in a new window or tabPre-Owned$14.25Was: $15.005% offor Best Offer+$6.40 deliveryExtra 5% off with couponSponsored
- 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 deliverySponsored
- Polo Ralph Lauren Chino Shorts Boys Sz 5 NavyOpens in a new window or tabPre-Owned$14.99or Best Offer+$4.99 deliverySponsored
- 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 deliverySponsored
- 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 moreSponsoredTop 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 returnsSponsored
- 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 deliverySponsored
- Denizen By Levi’s Boys Cargo Shorts Size 30 Academia Preppy Uniform KhakiOpens in a new window or tabBrand New$9.99or Best Offer+$8.24 deliverySponsored
- 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 deliverySponsored
- 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 returnsSponsoredTop Rated Plus
- 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 deliverySponsored
- 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 deliverySponsored
- Under Armour Boys Plaid Chino Shorts Size Small Blue Preppy GolfOpens in a new window or tabPre-Owned$11.36Was: $14.9524% offor Best Offer+$5.50 deliverySponsored
- 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 returnsSponsored
- 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 deliverySponsored
- Strasburg Boys Shorts Size 5 Solid White Dress Preppy NEWOpens in a new window or tabBrand New$20.00or Best Offer+$7.31 deliverySponsored
- Janie and Jack Connor Linen Lilac Shorts Sz 2 Toddler Boys Small Flat Front $39Opens in a new window or tabBrand New$9.99Buy It Now+$5.25 deliverySponsored
- Hanna Andersson Baggies Striped Terry Shorts Size 110 5 Green White 100% CottonOpens in a new window or tabPre-Owned$20.00or Best Offer+$4.84 deliverySponsored
- 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 deliverySponsored
- 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 deliverySponsored
- 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 deliverySponsored
- 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 deliverySponsored
- 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 deliverySponsored
- 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 deliverySponsored
- Crewcuts Green Embroidered Navy Scorpians Shorts Size 5 Boys Adjustable waistOpens in a new window or tabPre-Owned$13.05Was: $15.0013% offor Best Offer+$4.75 deliverySponsored
- Bella Bliss Boys Pull On Play Shorts Lot Size 5 & 6 Preppy SpringOpens in a new window or tabPre-Owned$50.00or Best Offer+$5.62 deliverySponsored
- 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 deliverySponsored
- 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 returnsSponsored
- 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 deliverySponsored
- 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 deliverySponsored
- 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 deliverySponsored
- 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 deliverySponsored
- 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 deliverySponsored
- 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 deliverySponsored
- 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 returnsSponsored
- 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 deliverySponsored
- Under Armour Match Play Cargo Golf ShortsOpens in a new window or tabPre-Owned$21.00or Best Offer+$9.84 deliverySponsored
- NWT Tailor Vintage Boys Pineapple Bermuda Shorts 8 ResortwearOpens in a new window or tabBrand New$22.99or Best Offer+$5.00 deliverySponsored
- 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 in 2-4 daysSponsored
- 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 deliverySponsored
