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- Vineyard Vines Shorts Boys Size 18 Blue Chino Whales Casual Preppy StretchOpens in a new window or tabPre-Owned$18.99or Best Offer+$5.95 deliveryFree returnsTop 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
- 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
- Brooks Brothers Shorts Youth Boy 18 Patchwork Plaid Cotton 28x10 Preppy AcademiaOpens in a new window or tabPre-Owned$16.99Was: $19.9915% offBuy It Now+$5.26 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
- Childrens Place Boys Plaid Shorts Size 7Opens in a new window or tabBrand New$13.95or Best Offer+$4.84 delivery
- 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
- HAWK Gray Checkered Preppy Shorts Youth Boys Size 7Opens in a new window or tabPre-Owned$4.50Was: $6.0025% offor Best Offer+$5.50 deliveryFree returnsTop Rated Plus
- 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
- 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
- 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
- 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
- Preppy Boys Shorts Gray Size 9 Tom SawyerOpens in a new window or tabPre-Owned$5.61Buy It Now+$5.19 delivery
- Children's Place Boys Shorts navy blue (size 7) adjust. waistOpens in a new window or tabPre-Owned$4.99or Best Offer+$4.99 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
- 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
- Vineyard Vines by Shep & Ian Boys Coral Shorts Size 18Opens in a new window or tabPre-Owned$9.95or Best Offer+$6.55 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
- 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
- Preppy Zara boys khaki basic tan shorts for school sz 9/10Opens in a new window or tabPre-Owned$10.00or Best Offer+$14.25 delivery
- Gap Kids Boys Khaki Shark Print Shorts Size 7 PreppyOpens in a new window or tabPre-Owned$14.99Buy It NowFree delivery
