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- The Oaks Apparel Size 5 Boys? Shorts Preppy Aqua Blue Linen Cotton BoutiqueOpens in a new window or tabPre-Owned$14.39Was: $15.9910% offor Best Offer+$6.99 delivery
- JANIE and JACK Preppy Stripe Cotton Adjustable Waist Flat Front Shorts I Sz 5Opens in a new window or tabPre-Owned$16.95or Best Offer+$6.55 delivery
- The Childrens Place Boys Size 5 Chino Shorts Beige Tan New With TagsOpens in a new window or tabBrand New$8.99or Best Offer+$6.40 delivery
- Boys Kids Cherokee Blue Plaid Classy Adj Waist Cargo Shorts 100% Cotton Sz 5Opens in a new window or tabPre-Owned$6.00or Best Offer+$5.85 delivery
- Polo by Ralph Lauren Boys Navy Blue Flat Front Cotton Chino Shorts 6X PreppyOpens in a new window or tabPre-Owned$25.00or Best Offer+$6.40 delivery
- Crewcuts Shorts Boy’s Size 5 Cotton Adjustable Waist Preppy - Easter - PurpleOpens in a new window or tabPre-Owned$11.00Buy It NowFree deliveryFree returnsTop Rated Plus
- Orient Expressed Vintage Boys Checked Shorts Sz 6 Easter Blue And Green PreppyOpens in a new window or tabPre-Owned$7.28or Best Offer+$5.75 delivery
- Vinyard Vines BOYS french terry shorts Size 6 PREPPY pink NWTOpens in a new window or tabBrand New$29.99Buy It Now+$5.50 delivery
- POLO Ralph Lauren Y2K Boys Size 6 Color Block Cotton Fleece Shorts with Logo EUCOpens in a new window or tabPre-Owned$15.50or Best Offer+$4.71 deliveryFree returns
- NWT Polo Ralph Lauren Boys Spa Terry Logo Graphic Athletic Shorts Navy 2/2TOpens in a new window or tabBrand New$28.00Buy It Now+$6.99 delivery
- Polo Ralph Lauren Boys Embroidered Colored Pony Yellow Preppy Shorts Size 5Opens in a new window or tabPre-Owned$22.99or Best Offer+$6.55 delivery
- Boys Gap Kids Navy Blue Shorts size 6 Adjust Waist Preppy SchoolOpens in a new window or tabPre-Owned$10.79Was: $11.9910% offBuy It NowFree delivery
- Vineyard Vines Boys Size 5 Mint Green Aqua Flat Front Deck Shorts 100% CottonOpens in a new window or tabPre-Owned$9.99or Best Offer+$4.71 delivery
- Polo by Ralph Lauren Multicolor Red Yellow Navy Madras Plaid Shorts Boys Size 5Opens in a new window or tabPre-Owned$24.99Buy It Now+$9.00 deliveryBenefits charity
- The Childrens Place Shorts Uniform Black Bundle Stretch Chino Size 5Opens in a new window or tabPre-Owned$15.00or Best Offer+$5.21 delivery in 2-4 days
- NWT Oshkosh Boy Khakis Shorts Kid Toddler Boy Many SizesOpens in a new window or tabBrand New$19.99or Best Offer+$5.21 delivery in 2-4 daysExtra 10% off with coupon
- Vineyard Vines Boys Size 5 Pink Flat Front Deck Shorts 100% CottonOpens in a new window or tabPre-Owned$19.97or Best Offer+$7.95 delivery
- Strasburg Boys Shorts Size 5 Solid White Dress Preppy NEWOpens in a new window or tabBrand New$20.00or Best Offer+$7.31 delivery
- 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
- Boys CRAZY 8 by Gymboree khaki shorts 5 NWT pull on elastic waist uniform schoolOpens in a new window or tabBrand New$8.95Buy It Now+$5.95 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
- HTF Boutique Zuccini Boys 6 Seersucker Nautical Lined Preppy Shorts nICE SHAPEOpens in a new window or tabPre-Owned$12.99Buy It Now+$5.99 delivery
- Old Navy Boys Preppy Gray Black Tropical Print Belted Chino Shorts Sz 5 NewOpens in a new window or tabBrand New$18.00or Best Offer+$6.40 delivery
- Wrangler Khakis Cargo Shorts Adjustable Waist Boys 5 And 6 NewOpens in a new window or tabBrand New$16.99Buy It Now+$7.35 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
- J. CREW CREWCUTS Boy's Sz 6 Preppy Plaid Shorts Cotton Adjustable Waist 6" InsOpens in a new window or tabPre-Owned$9.99Buy It Now+$5.90 delivery
- Boys CRAZY 8 by Gymboree navy blue dress shorts 5 NWT uniform school bottomsOpens in a new window or tabBrand New$8.95Buy It Now+$5.95 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
- Children’s Place Green Shorts Boys Size 5 Chinos Elastic Cotton Preppy Y2KOpens in a new window or tabPre-Owned$4.28Was: $4.7510% offor Best Offer+$6.40 delivery
- GYMBOREE Boys Sz 5 Preppy Patchwork Plaid Shorts Dogs Adjust Waist 7" InseamOpens in a new window or tabPre-Owned$7.99Buy It Now+$5.90 delivery
- Boden Size 6Y Yellow Chino Shorts Preppy Classic Cotton BlendOpens in a new window or tabPre-Owned$6.90Was: $19.7065% offor Best Offer+$6.40 deliveryFree returnsTop Rated Plus
- U.S. Polo ASSN Boys Sz 6 Shorts Blue Dark Washed Denim Summer Preppy OutdoorOpens in a new window or tabPre-Owned$7.00or Best Offer+$7.00 deliveryFree returnsExtra 10% off with couponTop Rated Plus
- Gymboree Toddler Boys Size 5 Multicolor Striped Chino Shorts Casual PreppyOpens in a new window or tabPre-Owned$13.99or Best Offer+$5.99 deliveryFree returnsTop Rated Plus
- Gap Boys Cargo Shorts Navy Adjustable Waist Size 5Opens in a new window or tabPre-Owned$7.99or Best Offer+$7.35 delivery
- Crewcuts Green Embroidered Navy Scorpians Shorts Size 5 Boys Adjustable waistOpens in a new window or tabPre-Owned$13.95Was: $15.007% offor Best Offer+$4.75 delivery
- Janie & Jack Preppy Plaid Shorts Size 6Opens in a new window or tabPre-Owned$24.00or Best Offer+$6.35 delivery
- Crazy 8 Orange & Navy Plaid Shorts- Size 5 Adjustable WaistOpens in a new window or tabPre-Owned$10.00or Best Offer+$4.71 delivery
- Janie and Jack Boys Size 5 / Plaid Shorts / CobaltOpens in a new window or tabPre-Owned$12.99or Best Offer+$4.99 delivery
- The Children’s Place Boy’s Flax Tan Uniform Stretch Twill Chino Shorts Size 6Opens in a new window or tabPre-Owned$12.00or Best Offer+$5.62 delivery
- Polo Ralph Lauren Shorts Boys Size 5 khaki Tan Cargo Rip Stop Military preppyOpens in a new window or tabPre-Owned$11.00or Best Offer+$4.84 delivery
