285 results
- 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
- Boys Tony Hawk Shorts Green Plaid Size 18 Skater PreppyOpens in a new window or tabPre-Owned$16.99or Best OfferFree deliverySponsored
- Polo Ralph Lauren Navy Blue Boy 10 Blue Pony Preppy Parachute Rugby Twill ShortsOpens in a new window or tabPre-Owned$24.99or Best Offer+$6.95 deliverySponsored
- Lacoste Boys Two Tone White/ Olive Green Logo Sweat Shorts W/Pockets Kids Sz 10Opens in a new window or tabPre-Owned$25.00or Best Offer+$8.54 deliverySponsored
- Chubbies Baby Blue 100% Cotton Shorts Boys Sz M Minimalist Preppy Beach CoastalOpens in a new window or tabPre-Owned$20.00or Best Offer+$4.33 deliverySponsored
- Vineyard Vines Kids Khaki Shorts Size 12 AdjustableOpens in a new window or tabPre-Owned$14.99or Best Offer+$6.95 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
- Vintage Ralph Lauren Polo Denim Shorts Chinos Short Boys Preppy 6Opens in a new window or tabPre-Owned$15.00or Best Offer+$4.00 deliverySponsored
Picked For You
Top selling items from trusted sellers | Sponsored- Vineyard Vines Boys 'Whale' Embroidered Club Shorts Stone $59.50 Size 12 nd 14Opens in a new window or tab$29.49coachjustyou (2,230) 100%2+ watchers
- Vineyard Vines Boys Cotton Summer Twill Club Shorts Antigua Green (14) $59.50Opens in a new window or tab$29.50coachjustyou (2,230) 100%
- Vineyard Vines Boys 'Whale' Embroidered Club Shorts Flag Blue $59.50 10,14,16Opens in a new window or tab$29.49coachjustyou (2,230) 100%
- Vineyard Vines Boys Gamefish Embroidered Seersucker Shorts Breaker Blue Size 16Opens in a new window or tab$39.00coachjustyou (2,230) 100%
- Gap Kids Boys Pull On Elastic Waistband Front & Back Pockets Stretch Soft 14/16Opens in a new window or tab$13.29titan27279 (5,793) 99.8%
- NWT Gap Boy's Elastic Waistband Stretch Soft Twill Shorts Size M (8) BlueOpens in a new window or tab$19.99julisant-58 (1,070) 99.7%
- N.W.D Gap Kids Boys Stretch Twill Shorts, Medieval Blue, Size L (10/12)Opens in a new window or tab$18.99julisant-58 (1,070) 99.7%
- Gap Kids Boys Pull On Elastic Waistband Front & Back Pockets Stretch Soft 14/16Opens in a new window or tab$13.29titan27279 (5,793) 99.8%
- Vineyard Vines Boys Kids 14 Blue Uniform Dress Shep Ian Chino Adjustable WaistOpens in a new window or tabPre-Owned$7.95Buy It Now+$5.95 deliverySponsored
- Polo Ralph Lauren Boys Size 10 White Cotton Bermuda Shorts Preppy YouthOpens in a new window or tabPre-Owned$24.70Was: $29.0615% offor Best Offer+$8.85 deliverySponsored
- Vineyard Vines Boys Seersucker Breaker Shorts Size 8Opens in a new window or tabPre-Owned$18.00or Best Offer+$9.45 deliverySponsored
- Cat & Jack Boys Size 5 Cat & Jack Quick Dry Blue Green Shark Board Shorts EUCOpens in a new window or tabPre-Owned$3.50Buy It Now+$3.50 deliveryFree returnsSponsored
- Ralph Lauren Shorts Boys 16 Green Yellow Colorblock Pony Preppy Vacation NEWOpens in a new window or tabBrand New$31.98Was: $39.9720% offor Best Offer+$6.99 deliverySponsored
- Vineyard Vines Shorts Boys Size 14 Beige Chino Casual Preppy Stretch LogoOpens in a new window or tabPre-Owned$19.99or Best Offer+$5.95 deliveryFree returnsSponsoredTop 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 returnsSponsoredTop Rated Plus
- Crewcuts Shorts Youth Boys Size 14 Pink PreppyOpens in a new window or tabPre-Owned$15.99Buy It Now+$5.26 deliverySponsored
- EUC Vineyard Vines Boys Size 14 Classic Bermuda Shorts Blue Embroidered LacrosseOpens in a new window or tabPre-Owned$14.95or Best Offer+$6.90 delivery in 2-4 daysSponsored
- Polo Ralph Lauren Chino Shorts Boys Sz 5 NavyOpens in a new window or tabPre-Owned$14.99or Best Offer+$4.99 deliverySponsored
- The Masters Collection Shorts Kids Boys Sz 5-6 Striped Embriodered Flags AOP REDOpens in a new window or tabBrand New$34.99or Best Offer+$6.55 deliveryExtra 14% off with couponSponsored
- Cat & Jack Pull-on Shorts - 2 Pair - Black and Gray - Size XLOpens in a new window or tabPre-Owned$10.00or Best Offer+$5.80 deliverySponsored
From our popular brands
Based on number of views and purchases | Sponsored- HurleyHurley Shorts Boys 22 Gray Chino Outdoors Casual Comfort PreppyOpens in a new window or tabPre-Owned$13.99+$6.99 deliveryExtra 15% off with coupon
- GapVintage Red Gap Kids Cargo Shorts size 8 Spring 2004 Line Y2K PreppyOpens in a new window or tabPre-Owned$15.00+$4.54 delivery
- GapLot Of 2 Gap Kids Boys Pull On Elastic Waist w/ Pockets Twill L (10/12) BlueOpens in a new window or tabBrand New$22.49+$5.80 delivery
- JordanJordan Jumpman Dri Fit Gray Basketball Shorts Cat Scratch Youth Large 12-13yrsOpens in a new window or tabPre-Owned$22.99+$6.55 delivery
- HurleyHurley Nike Dri-Fit Mens Boys 18 Gray Shorts Golf Casual Spring Summer PreppyOpens in a new window or tabPre-Owned$10.00+$4.84 delivery
- French Toast Boys Shorts Size 14 Tan Khaki Comfort Flex Elastic Waist StainOpens in a new window or tabPre-Owned$5.00or Best Offer+$5.62 deliverySponsored
- Vineyard Vines Boys Kids 12 Light Blue Uniform Dress Shep Ian Chino Flat FrontOpens in a new window or tabPre-Owned$7.95Buy It Now+$5.95 deliverySponsored
- Gymboree 4 4T Boys Shorts Plaid EUC adjustable waist preppy vintageOpens in a new window or tabPre-Owned$8.00or Best Offer+$4.95 deliverySponsored
- New boys 14-16 Cat & Jack Old Navy active shorts black gray lot pull on pocketsOpens in a new window or tabBrand New$7.79Was: $10.9929% offBuy It Now+$7.34 deliverySponsored
- JCrew Crew Cuts Performance Khakis Pants Drawstring Elastic Waist 8 10 NewOpens in a new window or tabBrand New$19.99Buy It Now+$5.95 deliverySponsored
- Cat & Jack Boys Size 18 Husky Thundering Gray Adjustable Waist Flat Front ShortsOpens in a new window or tabBrand New$13.00or Best Offer+$7.25 deliverySponsored
- Cat & Jack Kids Black Drawstring Shorts NWT size L 12/14Opens in a new window or tabBrand New$13.95Buy It NowFree deliveryLast oneSponsored
- Abercrombie Kids Shorts Boys Size 12 Blue White Preppy CottonOpens in a new window or tabPre-Owned$8.00or Best Offer+$5.49 deliverySponsored
- Brooks Brothers Shorts Youth Boy 18 Patchwork Plaid Cotton 28x10 Preppy AcademiaOpens in a new window or tabPre-Owned$19.99Buy It Now+$5.26 deliverySponsored
- Vineyard Vines Shorts Boys Size 12 Beige Chino Casual Preppy Stretch LogoOpens in a new window or tabPre-Owned$19.99or Best Offer+$5.95 deliveryFree returnsSponsoredTop Rated Plus
- Hurley Shorts Boys 22 Gray Chino Outdoors Casual Comfort PreppyOpens in a new window or tabPre-Owned$13.99Was: $19.9930% offor Best Offer+$6.99 delivery in 2-4 daysFree returnsExtra 15% off with couponSponsoredTop Rated Plus
- Vineyard Vines Boys Summer Twill Breaker Blue Adjustable Waist Shorts Size 14Opens in a new window or tabPre-Owned$16.00or Best Offer+$9.84 deliverySponsored
- 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 5% off with couponSponsoredTop Rated Plus
- Vineyard Vines Shep & Ian Boys 14 Chino Shorts Light Blue Preppy Shorts GolfOpens in a new window or tabPre-Owned$22.00or Best OfferFree deliverySponsored
- Vineyard Vines Boys Chino Shorts Khaki Cotton Twill Sz 12Opens in a new window or tabPre-Owned$9.59Was: $11.9920% offor Best Offer+$4.84 deliverySponsored
- 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
- Crewcuts Boys Size 7 Navy Blue 100% Linen Shorts Coastal Preppy Adjustable WaistOpens in a new window or tabPre-Owned$14.99or Best Offer+$4.95 deliverySponsored
- 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
- The Children's Place Boys Shorts Sz 6 Red Blue Pineapples Faded PreppyOpens in a new window or tabPre-Owned$15.00or Best Offer+$7.31 deliverySponsored
- 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 deliverySponsored
- Vineyard Vines Performance Shorts Boys 16 Pink BreathableOpens in a new window or tabPre-Owned$13.84or Best Offer+$5.99 deliveryFree returnsSponsoredTop Rated Plus
- Vintage Polo Ralph Lauren Shorts Tan Youth LargeOpens in a new window or tabPre-Owned$10.00Buy It Now+$6.10 deliverySponsored
- Polo Ralph Lauren Bermuda Shorts Boy's Size 16 Blue Emboidered Flags PreppyOpens in a new window or tabPre-Owned$14.40Was: $16.0010% offBuy It Now+$5.50 deliverySponsored
- Preppy Boys Shorts - Lot of 2 - Size 14 - Crew Cuts and Lands' End - CottonOpens in a new window or tabPre-Owned$13.60Was: $16.0015% offor Best Offer+$5.80 deliverySponsored
- Abercrombie Kids Shorts Lot Of 2 Boys Sz 13/14 Tan Cargo BlueOpens in a new window or tabPre-Owned$14.99or Best Offer+$7.99 deliveryFree returnsSponsored
- Cat And Jack Boys Pull On Shorts Sz XL 14 Blue/white/RedOpens in a new window or tabBrand New$14.41Was: $16.9515% offBuy It NowFree deliveryFree returnsSponsoredTop Rated Plus
- Vintage Youth Izod Lacoste Pocket Shorts Boys Size 4 Blue PreppyOpens in a new window or tabPre-Owned$2.80Was: $13.9980% offBuy It Now+$6.00 deliveryFree returnsSponsoredTop Rated Plus
- 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 deliverySponsored
- Oscar de la Renta Plaid Shorts 4YOpens in a new window or tabPre-Owned$50.00or Best Offer+$4.84 deliverySponsored
- AFTCO Boy fish Shorts Youth XL Coral Pink Flat Nylon 6” Inseam EUC Preppy NiceOpens in a new window or tabPre-Owned$19.99or Best Offer+$5.00 delivery in 2-4 daysSponsored
- Wonder Nation Boys Sz 6 Shorts Navy Blue Chino Flat Front Stretch Preppy SummerOpens in a new window or tabPre-Owned$4.00or Best Offer+$6.00 deliveryFree returnsExtra 5% off with couponSponsoredTop Rated Plus
- Kids Crown & Ivy Navy Flat Front Adjustable Shorts Size 14 Preppy Uniform ChurchOpens in a new window or tabPre-Owned$5.95or Best Offer+$5.80 deliverySponsored
- Lot of 2 Polo Ralph Lauren Boys Navy Blue and Cat & Jacks Shorts Size 7Opens in a new window or tabPre-Owned$13.99or Best Offer+$6.50 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
- 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 couponSponsoredTop Rated Plus
- GapKids Cotton Cargo Patchwork Madras Boys Shorts size 10Opens in a new window or tabPre-Owned$19.98or Best Offer+$7.80 deliveryFree returnsSponsoredTop Rated Plus
- Crewcuts Boys Sz 12 Stanton Shorts Stripe Blue White Shorts Preppy AK21Opens in a new window or tabPre-Owned$18.00Buy It Now+$6.55 deliverySponsored
- 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 deliverySponsored
- Gap Kids Boys Pull On Elastic Waistband Front & Back Pockets Stretch Soft 14/16Opens in a new window or tabBrand New$13.29Was: $18.9930% offor Best OfferFree deliverySponsored
- Gap Boy's Elastic Waistband Front & Back Pockets Stretch Soft Twill Shorts 10/12Opens in a new window or tabBrand New$12.59Was: $17.9930% offor Best OfferFree deliverySponsored
- Vineyard Vines Boys 16 Bermuda Shorts All Over Shark Print Logo Coral 28" x 9"Opens in a new window or tabPre-Owned$11.95or Best Offer+$5.00 deliveryFree returnsSponsoredTop 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+$8.35 delivery in 2-4 daysFree returnsSponsoredTop Rated Plus
- Vineyard Vines 12 Boys Seersucker Ocean Breeze Shorts NewOpens in a new window or tabBrand New$19.99Buy It Now+$8.00 deliverySponsored
- Cat And Jack Boys Pull On Shorts Sz XL 14 Green/BlackOpens in a new window or tabBrand New$16.11Was: $18.9515% offor Best OfferFree deliveryFree returnsSponsoredTop Rated Plus
- Cat And Jack Boys Pull On Shorts Sz XL 14 Green/yellow/BlackOpens in a new window or tabBrand New$14.41Was: $16.9515% offor Best OfferFree deliveryFree returnsSponsoredTop Rated Plus
- HAWK Gray Checkered Preppy Shorts Youth Boys Size 7Opens in a new window or tabPre-Owned$5.10Was: $6.0015% offor Best Offer+$5.50 deliveryFree returnsSponsoredTop Rated Plus
- 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
- And1 | Boy’s Blue Basketball ShortsOpens in a new window or tabPre-Owned$15.00or Best OfferFree deliverySponsored
- Vineyard Vines Boys Size 14 Green Breaker Shorts Uniform School Preppy NauticalOpens in a new window or tabPre-Owned$8.20Was: $10.0018% offBuy It Now+$5.49 deliverySponsored
- Murrays Toggery Shop Boys Sz 10 Shorts Nantucket Reds Cotton Adjustable WaistOpens in a new window or tabPre-Owned$21.60Was: $24.0010% offor Best OfferFree deliveryFree returnsSponsoredTop Rated Plus
- NWT Chubbies Boys Originals Stretch Short The Armadas Navy Blue Uniform PreppyOpens in a new window or tabBrand New$23.98or Best Offer+$4.84 deliverySponsored
- NWT Chubbies Boys Originals Stretch Short Khakinators Tan Khakis Uniform PreppyOpens in a new window or tabBrand New$23.98or Best Offer+$4.84 deliverySponsored
- CAT Boys Blue Puffer Vest size 5/6Opens in a new window or tabPre-Owned$7.00or Best Offer+$12.19 deliverySponsored
- Polo Ralph Lauren Blue Drawstring Preppy Shorts Boy's Size 14Opens in a new window or tabPre-Owned$17.00or Best Offer+$5.00 deliveryExtra 15% off with couponSponsored
- Vineyard Vines Boys 'Whale' Embroidered Club Shorts Stone $59.50 Size 12 nd 14Opens in a new window or tabBrand New$29.49Buy It NowFree deliveryFree returns2+ watchersSponsoredTop Rated Plus
- Items Per Page
