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- Polo Ralph Lauren Blue Drawstring Preppy Shorts Boy's Size 14Opens in a new window or tabPre-Owned$15.00or Best Offer+$7.00 delivery
- 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 delivery
- 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 returnsTop Rated Plus
- Crewcuts Boys Pink and Blue Striped Bermuda Seersucker Shorts Size 14Opens in a new window or tabPre-Owned$15.00or Best Offer+$5.80 deliveryFree returns
- 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 daysFree returnsSave up to 30% when you buy more
- Pantagonia Boys Fitz Stripe Board Shorts Swim Trunks Size 14 Beach Preppy ActiveOpens in a new window or tabPre-Owned$18.00Buy It Now+$4.71 delivery
- 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 delivery
- 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 delivery
- GAP Kids Gray Seersucker Shorts, Size Small 6/7, NEWOpens in a new window or tabBrand New$12.99or Best Offer+$5.31 delivery
- 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 deliveryFree returns4+ watchersTop Rated Plus
- Under Armour Boys Plaid Chino Shorts Size Small Blue Preppy GolfOpens in a new window or tabPre-Owned$11.06Was: $14.9526% offor Best Offer+$5.50 delivery
- 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 delivery
- 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 delivery
- Polo Ralph Lauren Shorts Kids Boys Small 8 Navy Blue Fleece Drawstring PreppyOpens in a new window or tabPre-Owned$18.00or Best Offer+$7.65 deliveryFree returnsTop Rated Plus
- 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 deliveryFree returnsTop Rated Plus
- 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 delivery
- 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 delivery
- Janie and Jack Connor Linen Lilac Shorts Sz 2 Toddler Boys Small Flat Front $39Opens in a new window or tabBrand New$9.99Buy It Now+$5.25 delivery
- Vineyard Vines Boys Size 14 Green Breaker Shorts Uniform School Preppy NauticalOpens in a new window or tabPre-Owned$10.00Buy It Now+$5.49 deliveryExtra 20% off with coupon
- 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 delivery
- 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 delivery
- 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 days
- Polo Ralph Lauren Shorts Boys 14 Brown Tan Chino Preppy Casual Kids YouthOpens in a new window or tabPre-Owned$15.00or Best OfferFree delivery
- Vineyard Vines Boys Light Baby Blue Preppy Casual Chino Cotton Shorts Size 14Opens in a new window or tabPre-Owned$22.00or Best Offer+$5.99 delivery
- 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 delivery
- Polo Ralph Lauren Boys Blue Chino Shorts Flat Front Sz 14 Preppy CoastalOpens in a new window or tabPre-Owned$14.00or Best Offer+$4.99 delivery
- 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 delivery
- Vineyard Vines Boys Cotton Summer Twill Club Shorts Antigua Green (14) $59.50Opens in a new window or tabBrand New$29.50Buy It NowFree deliveryFree 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 deliveryFree 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 delivery
- Vineyard Vines Kids Boys Cotton Summer Twill Club Shorts Starboard Green $59.50Opens in a new window or tabBrand New$34.49Buy It NowFree deliveryFree returnsTop Rated Plus
- 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 deliveryFree returnsTop Rated Plus
- Vineyard Vines Boys 'Whale' Embroidered Club Shorts SalmonOpens in a new window or tabPre-Owned$24.95Buy It Now+$9.45 delivery
- Vineyard Vines Bermuda Shorts Boys Youth Size 14 Beige VERY GOODOpens in a new window or tabPre-Owned$7.99Was: $9.9920% offBuy It Now+$7.00 delivery
- Vineyard Vines Shep & Ian Boys 14 Chino Shorts Light Blue Preppy Shorts GolfOpens in a new window or tabPre-Owned$22.00or Best OfferFree delivery
- Tommy Bahama boys blue drawstring shorts size Small(5-6)Opens in a new window or tabPre-Owned$11.99or Best Offer+$6.55 delivery
- 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 delivery
- Tailor Vintage Boys Size 14 Pink Bermuda ShortsOpens in a new window or tabPre-Owned$9.25or Best Offer+$6.99 delivery
- Vineyard Vines Shorts Boys 14 Blue Embroidered Lacrosse Lax Casual Preppy CottonOpens in a new window or tabPre-Owned$8.00Was: $10.0020% offor Best Offer+$4.80 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
- 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 delivery
- NWT There Abouts Boys Size 14 Lexington Light Green Chino Shorts MSRP $32Opens in a new window or tabBrand New$19.99Buy It Now+$5.71 delivery
- Boys Vineyard Vines Club Khaki Golf Shorts 3H0141- Size 14Opens in a new window or tabPre-Owned$9.97or Best Offer+$4.71 delivery
- 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 delivery
- 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 delivery
- Abercrombie & Fitch Gingham Plaid Shorts Boys Size 14 Blue White Bermuda PreppyOpens in a new window or tabPre-Owned$24.99or Best OfferFree deliveryFree returns
- 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 delivery
- Lot of Two Pair Boys Preppy Shorts Sz 14 Tucker & Tate Tony HawkOpens in a new window or tabPre-Owned$14.00or Best Offer+$10.84 delivery
- Buffalo David Bitton Boys Denim Parker Jean Shorts Fray Hem Distressed SZ 14Opens in a new window or tabPre-Owned$23.00or Best Offer+$7.50 delivery
- URBAN PIPELINE youth size 14 plaid bermuda shorts walking tan preppy beige surfOpens in a new window or tabPre-Owned$11.99Buy It NowFree delivery
- Vineyard Vines Seersucker Boat Embroidered Shorts Boys 14 Adjustable WaistOpens in a new window or tabPre-Owned$20.00or Best Offer+$6.55 delivery
- 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 delivery
