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- Polo Ralph Lauren Bermuda Shorts Kids 18 White Preppy Neutral Spring SummerOpens in a new window or tabPre-Owned$24.95or Best Offer+$6.75 delivery in 2-4 daysLocated in United StatesFree returnsTop Rated Plus
- 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
- 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 deliveryLocated in United States
- Vineyard Vines Kids Boys Cotton Club Shorts Starboard Green $59.50 size12,14,16Opens in a new window or tabBrand New$29.49Buy It NowFree deliveryLocated in United StatesFree returnsTop Rated Plus
- J.Crew Crewcuts Boys Dinosaur Bones Shorts Size 14 Green Adjustable Waist NWTOpens in a new window or tabBrand New$20.00Buy It Now+$6.36 deliveryLocated in United States
- 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
- 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+$6.02 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
Picked For You
Top selling items from trusted sellers | Sponsored- Vineyard Vines Kids Boys Cotton Club Shorts Starboard Green $59.50 size12,14,16Opens in a new window or tab$29.49coachjustyou (2,251) 100%
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- Vineyard Vines Boys Cotton Summer Twill Club Shorts Antigua Green (14) $59.50Opens in a new window or tab$29.50coachjustyou (2,251) 100%
- Vineyard Vines Boys 'Whale' Embroidered Club Shorts Flag Blue $59.50 10,14,16Opens in a new window or tab$29.49coachjustyou (2,251) 100%5+ watchers
- Vineyard Vines Breaker Shorts Boys 18 Khaki Casual Performance Adjustable WaistOpens in a new window or tabPre-Owned$17.95or Best Offer+$10.60 deliveryLocated in United States
- Vineyard Vines Camo Breaker Shorts Boys Size 18 Embroidered Dog Surfboard PreppyOpens in a new window or tabPre-Owned$16.02Was: $22.8830% offor Best Offer+$5.85 deliveryLocated in United StatesFree returnsTop Rated Plus
- NWT! Vineyard Vines Boys Sailors Red Performance Breaker Shorts Size 18Opens in a new window or tabBrand New$40.00or Best Offer+$4.69 delivery in 2-4 daysLocated 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+$4.58 delivery in 2-4 daysLocated in United States
- Under Armour boy sz 14 khaki performance shorts golf activewear preppyOpens in a new window or tabPre-Owned$16.50Was: $22.0025% offBuy It Now+$6.00 deliveryLocated in United States
- 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
- Polo Ralph Lauren Boys Size 18 Blue Chino Shorts Flat Front Preppy CottonOpens in a new window or tabPre-Owned$14.88or Best Offer+$6.99 delivery in 2-4 daysLocated in United StatesFree returnsTop Rated Plus
- Brooks Brothers Shorts Youth Boy 18 Patchwork Madras Plaid 28x10 Preppy AcademiaOpens in a new window or tabPre-Owned$17.42Was: $24.8830% offBuy It Now+$5.26 deliveryLocated in United States
- Boys Tony Hawk Shorts Green Plaid Size 18 Skater PreppyOpens in a new window or tabPre-Owned$7.99Was: $9.9920% offBuy It Now+$7.99 deliveryLocated in United States
- Nwt CLASS CLUB Dillard's MODERN FIT Boy's BLUE Stretch Twill CHINO Shorts Sz 14Opens in a new window or tabBrand New$9.00Was: $10.0010% offBuy It Now+$6.83 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+$8.45 delivery in 2-4 daysLocated in United States
- Ralph Lauren Polo Boys Cotton Ripstop Cargo Shorts Khaki Sz 14Opens in a new window or tabPre-Owned$15.00or Best Offer+$5.83 deliveryLocated in United States
- Polo Ralph Lauren Shorts Boy’s 18 Chino Golf Flat Front Preppy Khaki Tan 30x11Opens in a new window or tabPre-Owned$11.99or Best Offer+$5.90 deliveryLocated in United StatesFree returnsTop Rated Plus
- Boys Ralph Lauren Classic Polo Chino Shorts 18 29 in waist White Navy Ponys GolfOpens in a new window or tabPre-Owned$22.07Was: $23.998% offor Best Offer+$5.25 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 returns5+ watchersTop Rated Plus
- NWT Polo Ralph Lauren PREPSTER PACTHWORK INDIAN MADRAS Plaid Shorts Boys 18 PONYOpens in a new window or tabBrand New$36.99Buy It NowFree deliveryLocated in United StatesFree returns20% off 3+Top Rated Plus
- 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
- Polo Ralph Lauren Cargo Chino Shorts Boy's 18 White 100% Cotton Preppy BeachOpens in a new window or tabBrand New$25.00or Best Offer+$11.95 deliveryLocated in United States
- Vineyard Vines Boys 18 Pastel Stripe Pull On Shorts Preppy Cotton StretchOpens in a new window or tabPre-Owned$19.00or Best Offer+$8.00 deliveryLocated in United StatesFree returnsExtra 10% off with couponTop Rated Plus
- Vans Brown Multicolor Plaid Boys Shorts Size 18Opens in a new window or tabPre-Owned$2.00Was: $4.0050% offBuy It Now+$5.41 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+$12.11 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+$6.02 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
- 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+$10.60 deliveryLocated in United StatesFree returnsTop Rated Plus
- 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 deliveryLocated in United States
- NWT Brookstone Brothers Boy's Khaki Shorts Preppy Summer 18YOpens in a new window or tabBrand New$20.00or Best Offer+$5.95 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
- Vineyard Vines Navy Blue Performance Breaker Shorts Boys Size 14Opens in a new window or tabPre-Owned$18.00or Best Offer+$4.89 deliveryLocated in United States
- 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
- 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
- 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
- Ralph Lauren Boys Size 14 Bermuda Shorts Pink Plaid Preppy Easter Beach GolfOpens in a new window or tabPre-Owned$11.89Was: $13.9915% offBuy It Now+$7.01 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+$5.02 deliveryLocated in United States
- POLO Ralph Lauren Seersucker Shorts Preppy Blue White - Size Boy's 18Opens in a new window or tabPre-Owned$14.99or Best Offer+$10.60 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+$5.83 deliveryLocated in United StatesFree returnsTop Rated Plus
- 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
- Ralph Lauren Polo Boys Chino Cargo Shorts Olive Green ~ size 14 ~ NWTOpens in a new window or tabBrand New$22.00or Best Offer+$8.24 deliveryLocated in United StatesSave up to 20% when you buy more
- Vineyard Vines Bermuda Shorts Boys Youth Size 14 Beige VERY GOODOpens in a new window or tabPre-Owned$9.99Buy It Now+$8.90 delivery in 2-4 daysLocated 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
- GAP Kids Gray Seersucker Shorts, Size Small 6/7, NEWOpens in a new window or tabBrand New$12.99or Best Offer+$5.51 deliveryLocated in United States
- Tommy Bahama Boy's Blue Drawstring Shorts Size Small (5-6)Opens in a new window or tabPre-Owned$6.99or Best OfferFree deliveryLocated in United States
- Hurley Nike Dri-Fit Mens Boys Sz 18 Gray Shorts Golf Casual Spring Summer PreppyOpens in a new window or tabPre-Owned$11.70Was: $13.0010% offBuy It Now+$8.75 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
- Polo Ralph Lauren Pink Preppy Bermuda Long Shorts boys 18Opens in a new window or tabPre-Owned$22.00or Best Offer+$8.90 deliveryLocated in United States
- Vineyard Vines by Shep & Ian Boys Coral Chino Shorts Size 18Opens in a new window or tabPre-Owned$9.95or Best Offer+$7.90 deliveryLocated in United States
- Tommy Bahama boys blue drawstring shorts size Small(5-6)Opens in a new window or tabPre-Owned$11.99or Best Offer+$8.75 deliveryLocated in United States
- Vineyard Vines Boys Lobster Shorts Blue & Red Embroidered Size 14 ImmaculateOpens in a new window or tabPre-Owned$15.00or Best Offer+$10.60 deliveryLocated in United StatesExtra 15% off with coupon
- Kids Crown & Ivy Navy Flat Front Adjustable Shorts Size 14 Preppy Uniform ChurchOpens in a new window or tabPre-Owned$4.95or Best Offer+$6.02 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+$11.00 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 Khaki Shorts Youth Size 14 BoysOpens in a new window or tabPre-Owned$16.50Buy It Now+$8.30 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
- 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+$11.00 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
- 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
- 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
- Boys Vineyard Vines Club Khaki Golf Shorts 3H0141- Size 14Opens in a new window or tabPre-Owned$9.97or Best Offer+$4.89 deliveryLocated in United States
- 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 deliveryLocated in United States
- Vineyard Vines Boys 'Whale' Embroidered Club Shorts SalmonOpens in a new window or tabPre-Owned$24.95Buy It Now+$11.95 deliveryLocated in United States
- URBAN PIPELINE youth size 14 plaid bermuda shorts walking tan preppy beige surfOpens in a new window or tabPre-Owned$11.99Buy It NowFree deliveryLocated in United States
- Vineyard Vines Seersucker Boat Embroidered Shorts Boys 14 Adjustable WaistOpens in a new window or tabPre-Owned$20.00or Best Offer+$8.75 deliveryLocated in United States
- Lot of Two Pair Boys Preppy Shorts Sz 14 Tucker & Tate Tony HawkOpens in a new window or tabPre-Owned$14.00or Best Offer+$11.10 deliveryLocated in United States
- Children’s Place Green Shorts Boys Size 5 Chinos Elastic Cotton Preppy Y2KOpens in a new window or tabPre-Owned$4.51Was: $4.755% offor Best Offer+$8.30 deliveryLocated in United States
- Vineyard Vines Shep & Ian Boys 14 Chino Shorts Light Blue Preppy Shorts GolfOpens in a new window or tabPre-Owned$22.00or Best OfferFree deliveryLocated in United States
- 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 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
- NWT Brookstone Brothers Boy's Khaki Shorts Preppy Summer 14YOpens in a new window or tabBrand New$20.00or Best Offer+$5.95 deliveryLocated in United States
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