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- Crewcuts Boys Pink and Blue Striped Bermuda Seersucker Shorts Size 14Opens in a new window or tabPre-Owned$15.00or Best Offer+$5.80 deliveryLocated in United StatesFree returns
- Rip Curl Shorts Boys 23 Gray Chino Outdoors Casual Comfort PreppyOpens in a new window or tabPre-Owned$19.99or Best Offer+$6.99 deliveryLocated in United StatesFree returnsTop Rated Plus
- 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 deliveryLocated in United StatesFree returnsTop Rated Plus
- 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 deliveryLocated in United StatesFree returnsTop Rated Plus
- 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 deliveryLocated in United StatesFree returnsSave up to 30% when you buy moreTop Rated Plus
- Boys Under Armour Chino Golf Adjustable Waist Khaki Shorts size Youth MediumOpens in a new window or tabPre-Owned$11.00or Best Offer+$4.84 deliveryLocated in United States
- Vineyard Vines Navy Blue Performance Breaker Shorts Boys Size 14 EUC UniformOpens in a new window or tabPre-Owned$18.00or Best Offer+$5.00 deliveryLocated in United States
- 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
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 (2,249) 100%
- Vineyard Vines Kids Boys Cotton Summer Twill Club Shorts Starboard Green $59.50Opens in a new window or tab$34.49coachjustyou (2,249) 100%
- Vineyard Vines Boys Cotton Summer Twill Club Shorts Antigua Green (14) $59.50Opens in a new window or tab$29.50coachjustyou (2,249) 100%
- Vineyard Vines Boys 'Whale' Embroidered Club Shorts Flag Blue $59.50 10,14,16Opens in a new window or tab$29.49coachjustyou (2,249) 100%4+ watchers
- Nwt CLASS CLUB Dillard's MODERN FIT Boy's BLUE Stretch Twill CHINO Shorts Sz 14Opens in a new window or tabBrand New$10.80Was: $12.0010% offBuy It Now+$6.62 deliveryLocated in United States
- 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
- EUC Vineyard Vines Boys Size 14 Classic Bermuda Shorts Blue Embroidered LacrosseOpens in a new window or tabPre-Owned$15.95or Best Offer+$6.90 delivery in 2-3 daysLocated in United States
- NWT Crewcuts Boy’s Stanton Seersucker Chino Shorts Blue White Striped Cotton 14Opens in a new window or tabBrand New$19.99Was: $39.9950% offor Best Offer+$7.35 deliveryLocated in United StatesFree returns
- Polo Ralph Lauren Boys Prepster Shorts Sz 14 Chambray BlueOpens in a new window or tabPre-Owned$18.00or Best Offer+$9.91 deliveryLocated in United States
- 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 deliveryLocated in United States
- Polo Ralph Lauren Blue Drawstring Preppy Shorts Boy's Size 14Opens in a new window or tabPre-Owned$15.00or Best Offer+$7.00 deliveryLocated in United StatesExtra 15% off with coupon
- Vineyard Vines Kids Boys Cotton Summer Twill Club Shorts Starboard Green $59.50Opens in a new window or tabBrand New$34.49Buy It NowFree deliveryLocated in United StatesFree returnsTop Rated Plus
- NWT There Abouts Boys Size 14 Lexington Light Green Chino Shorts MSRP $32Opens in a new window or tabBrand New$20.99Buy It Now+$5.71 deliveryLocated in United States
- Janie & Jack Boys’ Linen Blend Shorts Blue Chambray Size 14 Stretch WaistOpens in a new window or tabPre-Owned$10.00Buy It Now+$4.41 delivery in 2-4 daysLocated in United States
- Polo Ralph Lauren Cotton Twill Shorts Boys 14 Multicolored CP RL-93 Logo PonyOpens in a new window or tabPre-Owned$18.00Buy It Now+$5.80 deliveryLocated in United States
- Gap Boy's Elastic Waistband Front & Back Pockets Stretch Soft Twill ShortsOpens in a new window or tabPre-Owned$7.99Buy It Now+$6.55 deliveryLocated in United States
- 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
- Hannah Andersson Terry cloth shorts boys 8 pull on drawstring beach summerOpens in a new window or tabPre-Owned$9.74Was: $12.9925% offBuy It Now+$4.84 deliveryLocated in United States
- The Children's Place Boys Khaki Navy Cargo Pull On Adjustable Shorts Sz 14 HuskyOpens in a new window or tabPre-Owned$19.99or Best Offer+$10.00 deliveryLocated in United States
- Ralph Lauren Boys Size 14 Bermuda Shorts Pink Plaid Preppy Easter Beach GolfOpens in a new window or tabPre-Owned$13.99Buy It Now+$7.01 deliveryLocated in United States
- NWT Polo Ralph Lauren PREPSTER PACTHWORK INDIAN MADRAS Plaid Shorts Boys 14 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 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
- 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 14 Plaid Shorts Blue Green Shep Ian Preppy 100% CottonOpens in a new window or tabPre-Owned$16.00or Best Offer+$4.84 deliveryLocated in United States
- Vineyard Vines Boys Cotton Summer Twill Club Shorts Antigua Green (14) $59.50Opens in a new window or tabBrand New$29.50Buy It NowFree deliveryLocated in United StatesFree returnsTop Rated Plus
- Vineyard Vines Coral Bermuda Boys Kids Shorts Preppy 14 323 PreppyOpens in a new window or tabPre-Owned$12.95Buy It Now+$6.00 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
- Vineyard Vines Boys 'Whale' Embroidered Club Shorts Flag Blue $59.50 10,14,16Opens in a new window or tabBrand New$29.49Buy It NowFree deliveryLocated in United StatesFree returns4+ watchersTop 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 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
- 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
- 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
- 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
- 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
- Vineyard Vines Boys BurgeeFlag Embroidery Club Shorts Ocean Splash 14 Blue NWTOpens in a new window or tabBrand New$20.00Buy It Now+$5.80 deliveryLocated in United States
- J.Crew Boys Crewcuts Active Shorts Size 8 Brown Tan Outdoors Training PreppyOpens in a new window or tabPre-Owned$16.78Was: $20.9820% offBuy It Now+$5.84 deliveryLocated in United States
- EUC Boys Vineyard Vines Striped Seersucker Shorts Sz-14Opens in a new window or tabPre-Owned$19.99Buy It NowFree 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
- Vineyard Vines Shorts Boys Size 14 Beige Chino Casual Preppy Adj WaistOpens in a new window or tabPre-Owned$16.00Buy It Now+$5.00 deliveryLocated in United States
- Boys Size 8 * J Crew Crewcuts* Lot Of 4 Items Polos And Shorts* Blue NauticalOpens in a new window or tabPre-Owned$35.00Buy It Now+$8.71 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
- 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
- Polo Ralph Lauren Boys Blue Chino Shorts Flat Front Sz 14 Preppy CoastalOpens in a new window or tabPre-Owned$9.80Was: $14.0030% offor Best Offer+$4.99 deliveryLocated in United States
- Vtg Polo Ralph Lauren Shorts Chino Khaki Boys Size 14 Beige Preppy Golf PonyOpens in a new window or tabPre-Owned$19.99or Best Offer+$10.10 deliveryLocated in United States
- Vineyard Vines Boys Lobster Print Shorts Navy Blue & Red Size Size 14 ImmaculateOpens in a new window or tabPre-Owned$18.50or Best Offer+$7.35 deliveryLocated in United States
- NWT Brooks Brothers Big Boys Pull-On Fleece Shorts Coral Preppy 14Opens in a new window or tabBrand New$20.00or Best Offer+$5.95 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
- 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
- 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
- Kids Crown & Ivy Navy Flat Front Adjustable Shorts Size 14 Preppy Uniform ChurchOpens in a new window or tabPre-Owned$4.95or 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$11.21Was: $13.6718% offor Best Offer+$6.55 deliveryLocated in United States
- Vineyard Vines Seersucker Shorts Size 14 Boy Spring Summer Country Club PreppyOpens in a new window or tabPre-Owned$22.50or Best Offer+$8.71 deliveryLocated in United States
- Polo Ralph Lauren Denim Shorts Jorts 100% Cotton 10" Inseam Preppy Boys 14Opens in a new window or tabPre-Owned$19.98or Best Offer+$5.62 deliveryLocated in United StatesFree returnsExtra 15% off with couponTop Rated Plus
- Lot Of 2 Old Navy Boys School Uniform Pants, Khaki Flat Front Adjustable Size 14Opens in a new window or tabPre-Owned$12.00Buy It Now+$11.07 deliveryLocated in United States
- Abercrombie & Fitch Gingham Plaid Shorts Boys Size 14 Blue White Bermuda PreppyOpens in a new window or tabPre-Owned$24.99or Best OfferFree deliveryLocated in United StatesFree returns
- Vineyard Vines Bermuda Shorts Boys Youth Size 14 Beige VERY GOODOpens in a new window or tabPre-Owned$6.99Was: $9.9930% offBuy It Now+$7.00 deliveryLocated in United States
- Tailor Vintage Boys Size 14 Pink Bermuda ShortsOpens in a new window or tabPre-Owned$8.00or Best Offer+$6.99 deliveryLocated in United States
- Lot Of 2 Old Navy Boys School Uniform Pants, Khaki Flat Front Adjustable Size 14Opens in a new window or tabPre-Owned$12.00Buy It Now+$11.07 deliveryLocated in United States
- 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 deliveryLocated in United States
- Vineyard Vines Boys Seersucker Breaker Shorts Size 8Opens in a new window or tabPre-Owned$9.90Was: $18.0045% offor Best Offer+$9.45 deliveryLocated in United States
- Vtg Polo Ralph Lauren Shorts Chino Khaki Boys Size 14 Navy Blue Preppy Golf PonyOpens in a new window or tabPre-Owned$19.99or Best Offer+$10.10 deliveryLocated in United States
- Vineyard Vines Shorts Boys 14 Blue Embroidered Lacrosse Lax Casual Preppy CottonOpens in a new window or tabPre-Owned$10.00or Best Offer+$4.80 deliveryLocated in United States
- Vineyard Vines Breaker Shorts Blue Twill Cotton Casual Stretch Youth Boys 14Opens in a new window or tabBrand New$49.99Buy It Now+$6.99 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+$9.45 deliveryLocated in United States
- Boys Vineyard Vines Club Khaki Golf Shorts 3H0141- Size 14Opens in a new window or tabPre-Owned$9.97or Best Offer+$4.71 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
- White Blue Striped Preppy Shorts Boy’s 8 Adjustable Waist Lightweight Fall trendOpens in a new window or tabPre-Owned$18.00or Best Offer+$9.45 deliveryLocated in United States
- Vineyard Vines Shorts Boys Size 14 Beige Chino Casual Preppy Stretch LogoOpens in a new window or tabPre-Owned$15.00Buy It Now+$5.62 deliveryLocated in United States
- 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
- NWT Brooks Brothers Big Boys Pull-On Fleece Shorts Coral Preppy 14Opens in a new window or tabBrand New$20.00or Best Offer+$5.95 deliveryLocated in United States
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