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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 delivery in 2-4 daysLocated in United StatesFree 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 deliveryLocated in United States
- J Khaki Lobster Embrodiered shorts Khaki Chino’s Preppy 31wOpens in a new window or tabPre-Owned$25.00or Best Offer+$9.00 deliveryLocated in United States
- Polo Ralph Lauren Shirt Boys Size XL (18-20) Blue Striped Preppy Red Pony GolfOpens in a new window or tabPre-Owned$18.00or Best Offer+$6.00 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
- Polo Ralph Lauren Shirt Boys Size XL (18-20) Blue Orange Striped Preppy CasualOpens in a new window or tabPre-Owned$17.99or Best Offer+$5.99 deliveryLocated in United StatesFree returnsTop Rated Plus
- NWT! Vineyard Vines Boys Sailors Red Performance Breaker Shorts Size 18Opens in a new window or tabBrand New$40.00or Best Offer+$4.69 deliveryLocated in United States
- Polo Ralph Lauren Cargo Chino Shorts Boy's 18 White 100% Cotton Preppy BeachOpens in a new window or tabBrand New$25.00or Best Offer+$11.95 deliveryLocated in United States
- Vineyard Vines Camo Breaker Shorts Boys Size 18 Embroidered Dog Surfboard PreppyOpens in a new window or tabPre-Owned$22.88or Best Offer+$5.85 deliveryLocated in United StatesFree returnsTop Rated Plus
- Ralph Lauren Polo Boys Size XL 18-20 Navy Pull On Cargo Shorts Casual Preppy RedOpens in a new window or tabPre-Owned$15.00or Best Offer+$10.60 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
- 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
- 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 deliveryLocated in United StatesFree returnsTop Rated Plus
- NWT CREWCUTS CHINO SHORTS BOYS SIZE 4 YELLOW SPRING EASTEROpens in a new window or tabBrand New$12.99Was: $19.9935% offor Best Offer+$6.95 deliveryLocated in United StatesFree returns
- Lot Of 2 Gap Kids Boys Pull On Elastic Waist w/ Pockets Twill XL (14/16) GreenOpens in a new window or tabBrand New$29.99or Best Offer+$6.02 deliveryLocated in United States
- Vintage Youth Izod Lacoste Pocket Shorts Boys Size 4 Blue PreppyOpens in a new window or tabPre-Owned$13.99Buy It Now+$7.00 deliveryLocated in United StatesFree returnsTop Rated Plus
- Carters Kids Size 4 Chino Short Blue Adjustable Waist Casual Stretch PreppyOpens in a new window or tabBrand New$9.85or Best Offer+$5.83 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
- NEW Boys La Jenns 4T Brown Gingham Shorts PreppyOpens in a new window or tabBrand New$12.00or Best Offer+$4.50 deliveryLocated in United States
- Vans Brown Multicolor Plaid Boys Shorts Size 18Opens in a new window or tabPre-Owned$2.00Was: $4.0050% offBuy It Now+$5.41 deliveryLocated in United States
- Polo Ralph Lauren Shorts Boy’s 18 Chino Golf Flat Front Preppy Khaki Tan 30x11Opens in a new window or tabPre-Owned$11.99or Best Offer+$5.90 deliveryLocated in United StatesFree returnsTop Rated Plus
- 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
- Hurley Nike Dri-Fit Mens Boys Sz 18 Gray Shorts Golf Casual Spring Summer PreppyOpens in a new window or tabPre-Owned$11.25Was: $12.5010% offBuy It Now+$8.75 deliveryLocated in United StatesExtra 10% off with coupon
- NWT Brookstone Brothers Boy's Khaki Shorts Preppy Summer 18YOpens in a new window or tabBrand New$20.00or Best Offer+$5.95 deliveryLocated in United States
- JANIE AND JACK Boys’ Blue Pink Plaid Linen Blend Shorts Size 4 Preppy CountryOpens in a new window or tabPre-Owned$12.99Buy It Now+$9.02 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+$10.60 deliveryLocated in United States
- Gymboree 4 4T Boys Shorts Plaid EUC adjustable waist preppy vintageOpens in a new window or tabPre-Owned$8.75or Best Offer+$4.95 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 2-4 daysLocated in United StatesFree returnsTop Rated Plus
- GAP Boy's Elastic Waistband Front & Back Pockets Soft Twill Shorts ,NewOpens in a new window or tabBrand New$14.99Buy It Now+$4.61 deliveryLocated in United States
- J.Crew Crewcuts BOYS GRAMERCY COTTON DINO SHORT, Size 4, imperial Blue GreenOpens in a new window or tabPre-Owned$18.95or Best Offer+$8.75 deliveryLocated in United States
- Oshkosh Genuine Kids Plaid Cargo Shorts Boys Size 4T Preppy Casual Summer Y2KOpens in a new window or tabPre-Owned$4.75Was: $5.005% offBuy It Now+$8.30 deliveryLocated in United States
- Polo Ralph Lauren Boys Straight Fit Stretch Golf Shorts Size 4 NewOpens in a new window or tabBrand New$25.00or Best Offer+$8.75 deliveryLocated in United States
- Gap Kids Boys Size 4 Madras Patchwork Plaid Adjustable Waist ShortsOpens in a new window or tabPre-Owned$7.99or Best Offer+$5.60 deliveryLocated in United StatesFree returnsTop Rated Plus
- POLO RALPH LAUREN BOY Preppy Pleated Bermuda Chino Summer Shorts 4 Yrs KhakiOpens in a new window or tabPre-Owned$9.99or Best Offer+$8.70 delivery in 2-4 daysLocated in United StatesFree returnsTop Rated Plus
- 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
- Vineyard Vines by Shep & Ian Boys Coral Chino Shorts Size 18Opens in a new window or tabPre-Owned$9.95or Best Offer+$7.90 deliveryLocated in United States
- Brooks Brothers Shorts Youth Boy 18 Patchwork Madras Plaid 28x10 Preppy AcademiaOpens in a new window or tabPre-Owned$24.88Buy It Now+$5.26 deliveryLocated in United States
- Mini Boden Boy's Techno Shorts Size 4Y Bermudas Brown Blue PreppyOpens in a new window or tabPre-Owned$12.50or Best Offer+$5.50 deliveryLocated in United States
- GAP Boy's Elastic Waistband Front & Back Pockets Soft Twill Shorts ,NewOpens in a new window or tabBrand New$10.00or Best Offer+$5.02 deliveryLocated in United States
- Seed heritage 4 boys lobster print casual summer beach shorts cotton preppyOpens in a new window or tabPre-Owned$16.00Was: $20.0020% offor Best Offer+$4.99 deliveryLocated in United States
- Oscar de la Renta Plaid Shorts 4YOpens in a new window or tabPre-Owned$50.00or Best Offer+$5.02 deliveryLocated in United States
- Gap Boy Elastic Waistband Pockets Stretch Soft Twill Shorts Green XL 14/16 NWTOpens in a new window or tabBrand New$13.67or Best Offer+$8.75 deliveryLocated in United States
- Cat & Jack Boys Flat Front Shorts Green Size 4Opens in a new window or tabPre-Owned$6.97or Best Offer+$5.02 deliveryLocated in United States
- Crewcuts Boys Blue Seersucker Shorts Size 12 NEW W TAG Preppy Shorts Boys XLOpens in a new window or tabBrand New$36.99or Best Offer+$9.99 deliveryLocated in United States
