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- Polo Ralph Lauren Bermuda Shorts Kids 18 White Preppy Neutral Spring SummerOpens in a new window or tabPre-Owned$24.95or Best Offer+$6.75 deliveryLocated in United StatesFree returnsExtra 10% off with couponTop 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 deliveryLocated in United States
- Polo Ralph Lauren Boy’s 18 Chino Golf Shorts Flat Front Preppy Khaki Tan 30x11Opens in a new window or tabPre-Owned$13.99or Best Offer+$5.90 deliveryLocated in United StatesFree returnsTop Rated Plus
- Brooks Brothers Shorts Youth Boy 18 Patchwork Madras Plaid 28x10 Preppy AcademiaOpens in a new window or tabPre-Owned$17.42Was: $24.8830% offor Best Offer+$5.26 deliveryLocated in United States
- 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 delivery in 2-4 daysLocated in United StatesFree returnsSave up to 30% when you buy moreTop Rated Plus
- Class Club Boy's Size 8 Navy Blue Modern Fit Adjustable Waist Shorts UniformOpens in a new window or tabPre-Owned$8.88or Best Offer+$2.89 deliveryLocated in United States
- Hanna Andersson cargo shorts boys 130 8 navy blue cotton adjustable waist preppyOpens in a new window or tabPre-Owned$12.99Buy It Now+$6.00 deliveryLocated in United States
- Boys Ralph Lauren Classic Polo Chino Shorts 18 29 in waist White Navy Ponys GolfOpens in a new window or tabPre-Owned$22.07Was: $23.998% offor Best Offer+$5.25 deliveryLocated in United States
- Vineyard Vines Boys 18 Pastel Stripe Pull On Shorts Preppy Cotton StretchOpens in a new window or tabPre-Owned$19.00or Best Offer+$8.00 deliveryLocated in United StatesFree returnsExtra 10% off with couponTop Rated Plus
- Tommy Hilfiger Boys Shorts Pockets Navy Blue Size M 12/14Opens in a new window or tabPre-Owned$9.99Buy It NowFree deliveryLocated in United States
- Boys Tony Hawk Shorts Green Plaid Size 18 Skater PreppyOpens in a new window or tabPre-Owned$7.99Was: $9.9920% offBuy It Now+$7.99 deliveryLocated in United States
- Hurley Nike Dri-Fit Mens Boys Sz 18 Gray Shorts Golf Casual Spring Summer PreppyOpens in a new window or tabPre-Owned$11.70Was: $13.0010% offBuy It Now+$6.55 deliveryLocated in United States
- Wonder Nation Boys Sz 18 Shorts Blue Flat Front Chino Stretch Adjustable PreppyOpens in a new window or tabPre-Owned$4.00or Best Offer+$7.00 deliveryLocated in United StatesFree returnsExtra 10% off with couponTop Rated Plus
- J.Crew Boys Crewcuts Active Shorts Size 8 Brown Tan Outdoors Training PreppyOpens in a new window or tabPre-Owned$20.98Buy It Now+$5.84 deliveryLocated in United States
- Polo Ralph Lauren Boys Size 18 Blue Chino Shorts Flat Front Preppy CottonOpens in a new window or tabPre-Owned$14.88or Best Offer+$6.99 delivery in 2-3 daysLocated in United StatesFree returnsTop Rated Plus
- Rip Curl Shorts Boys 23 Gray Chino Outdoors Casual Comfort PreppyOpens in a new window or tabPre-Owned$6.00Was: $19.9970% offor Best Offer+$6.99 delivery in 2-4 daysLocated in United StatesFree returnsExtra 15% off with couponTop Rated Plus
- NWT Gap Boy's Elastic Waistband Stretch Soft Twill Shorts Size M (8) BlueOpens in a new window or tabBrand New$13.49Was: $14.9910% offor Best Offer+$5.80 deliveryLocated in United States
- 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 deliveryLocated in United StatesFree returnsTop Rated Plus
- Vineyard Vines Boys Performance Short Red Size 8Opens in a new window or tabPre-Owned$15.00or Best OfferFree deliveryLocated in United States
- Polo Ralph Lauren Boys Chino Shorts Navy Blue NWT Size 14 Youth Kids PreppyOpens in a new window or tabBrand New$19.95Buy It Now+$4.84 deliveryLocated in United States
From our popular brands
Based on number of views and purchases | Sponsored- NikePre-Owned$11.70+$6.55 delivery
- GapNew (Other)$12.95+$6.95 delivery
- GapPre-Owned$8.99+$5.75 delivery
- 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 deliveryLocated in United States
- POLO Ralph Lauren Seersucker Shorts Preppy Blue White - Size Boy's 18Opens in a new window or tabPre-Owned$14.99or Best Offer+$7.35 deliveryLocated in United States
- Hannah Andersson Terry cloth shorts boys 8 pull on drawstring beach summerOpens in a new window or tabPre-Owned$10.39Was: $12.9920% offBuy It Now+$4.84 deliveryLocated in United States
- Crewcuts Boys Blue Seersucker Shorts Size 8 NEW W TAG Preppy Shorts Size SmallOpens in a new window or tabBrand New$36.99Buy It Now+$9.99 deliveryLocated in United States
- HURLEY Boys Plaid Shorts SIZE 8 Navy 100% Cotton Pockets LOGOsOpens in a new window or tabPre-Owned$9.95Buy It Now+$5.99 deliveryLocated in United States
- IZOD Boys Plaid Shorts SIZE 8 Blue Adjustable Waist 100% Cotton PocketsOpens in a new window or tabPre-Owned$9.95Buy It Now+$5.99 deliveryLocated in United States
- NWT Polo Ralph Lauren PREPSTER PACTHWORK INDIAN MADRAS Plaid Shorts Boys 18 PONYOpens in a new window or tabBrand New$36.99Buy It NowFree deliveryLocated in United StatesFree returns20% off 3+Top Rated Plus
- Polo Ralph Lauren Boys Sz 8 Seersucker Shorts Blue White Adj WaistOpens in a new window or tabPre-Owned$15.00Buy It Now+$6.25 deliveryLocated in United States
- NWOT Gap Kids Boys Stretch Twill Shorts Navy Blue Sz M (8) 98%cotton 2% spandexOpens in a new window or tabNew (Other)$12.95Buy It Now+$6.95 deliveryLocated in United States
- Vineyard Vines Boys Seersucker Breaker Shorts Size 8Opens in a new window or tabPre-Owned$18.00or Best Offer+$9.45 deliveryLocated in United States
- Gap Shorts Boys Medium Husky Chino Khaki Bermuda Tan Elastic Drawstring Waist MOpens in a new window or tabPre-Owned$8.99or Best Offer+$5.75 deliveryLocated in United StatesFree 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 deliveryLocated in United States
- Gap Boy's Navy Elastic Waistband Front & Back Pockets Stretch Soft Twill ShortsOpens in a new window or tabBrand New$13.56Was: $16.9520% offBuy It NowFree deliveryLocated in United States
- 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 deliveryLocated in United States
- Children's Place Size 8 Burnt Orange/Red Boys Chino Shorts Stylish Preppy SummerOpens in a new window or tabPre-Owned$9.99or Best Offer+$4.84 deliveryLocated in United States
- Vineyard Vines by Shep & Ian Boys Coral Chino Shorts Size 18Opens in a new window or tabPre-Owned$9.95or Best Offer+$5.85 deliveryLocated in United States
- 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 deliveryLocated in United States
- 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 deliveryLocated in United States
- 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 deliveryLocated in United States
- Gap Boy Elastic Waistband Pockets Stretch Soft Twill Shorts Green M 8 NWTOpens in a new window or tabBrand New$13.67or Best Offer+$6.55 deliveryLocated in United States
- Polo Ralph Lauren Pink Preppy Bermuda Long Shorts boys 18Opens in a new window or tabPre-Owned$22.00or Best Offer+$8.90 deliveryLocated in United States
- Zara Blue Flat Front Shorts Boys Size 8 Linen Blend Preppy Casual Summer CoastalOpens in a new window or tabPre-Owned$16.00or Best Offer+$14.25 deliveryLocated in United States
- NWT Tailor Vintage Boys Pineapple Bermuda Shorts 8 ResortwearOpens in a new window or tabBrand New$22.99or Best Offer+$5.00 deliveryLocated in United States
- Vans Brown Multicolor Plaid Boys Shorts Size 18Opens in a new window or tabPre-Owned$4.00Buy It Now+$5.21 deliveryLocated in United States
- 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 deliveryLocated in United StatesFree returnsTop 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 deliveryLocated in United States
- VGUC JCrew M Boys Shorts Chambray Blue Elastic Pull On Preppy School DrawstringOpens in a new window or tabPre-Owned$15.00or Best Offer+$5.00 delivery in 2-4 daysLocated in United States
- 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 deliveryLocated in United States
- White Blue Striped Preppy Shorts Boy’s 8 Adjustable Waist Lightweight Fall trendOpens in a new window or tabPre-Owned$15.00or Best Offer+$64.03 deliveryLocated in United States
- White Blue Striped Preppy Shorts Boy’s 8 Adjustable Waist Lightweight Fall trendOpens in a new window or tabPre-Owned$18.00or Best Offer+$75.21 deliveryLocated in United States
- Columbia Youth Medium Blue Chino Shorts Outdoors Gorpcore Preppy HikingOpens in a new window or tabPre-Owned$14.50Buy It Now+$6.55 deliveryLocated in United States
