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- Vineyard Vines Performance Shorts Boys 14 Beige Chino Adjustable Waist Preppy A1Opens in a new window or tabPre-Owned$17.95or Best Offer+$5.95 deliveryLocated in United StatesFree returnsExtra 20% off with couponTop Rated Plus
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- Under Armour Chino Shorts Youth Boys 14 Blue Loose Drive Athletic GolfOpens in a new window or tabPre-Owned$15.82Was: $19.7720% offor Best Offer+$7.45 deliveryLocated in United StatesFree returns
- Tommy Bahama Short Boys Sz Small Hybrid Casual Elastic Waist Pull-On Comfy BeachOpens in a new window or tabPre-Owned$3.66Was: $7.3250% offor Best Offer+$4.99 deliveryLocated in United StatesFree returnsExtra 15% off with couponTop 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
- Gap Kids Boys Pull On Soft Stretch Twill Woven ShortOpens in a new window or tabBrand New$14.99List price: $30.9952% offBuy It NowFree deliveryLocated in United StatesFree returnsTop Rated Plus
- Polo Ralph Lauren boys size 7 beige cotton classic polo chino shortsOpens in a new window or tabPre-Owned$14.99or Best OfferFree deliveryLocated in United StatesFree returns
- Polo Ralph Lauren Shorts Boys Size 14 Khaki Cotton Cargo Drawstring YouthOpens in a new window or tabPre-Owned$11.49or Best Offer+$7.35 deliveryLocated in United StatesFree returnsExtra 15% off with couponTop Rated Plus
Picked For You
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- 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%5+ watchers
- Pure Stuff Shorts Boys 14 Navy Golf Preppy Church Pockets Cargo Uniform ChinoOpens in a new window or tab$15.99connectedthreads (2,070) 99.8%
- Polo Ralph Lauren Shorts Youth Boys 14 Khaki Bear All Over Embroidered LogoOpens in a new window or tabPre-Owned$17.36Was: $19.9513% offBuy It Now+$9.45 deliveryLocated in United StatesFree returnsTop Rated Plus
- Izod Shorts Boys 14 Blue Red Plaid Flat Front Zip Pockets Summer Classic PreppyOpens in a new window or tabPre-Owned$22.99or Best Offer+$5.95 deliveryLocated in United StatesFree returns
- Polo Ralph Lauren Boy's Chino Shorts Size 14 Tan Preppy 9" InseamOpens in a new window or tabPre-Owned$9.69or Best Offer+$7.02 deliveryLocated in United StatesFree returnsTop Rated Plus
- Vineyard Vines Performance Boys Blue Shorts Size 14 Golf PreppyOpens in a new window or tabPre-Owned$17.95Buy It Now+$7.99 deliveryLocated in United StatesFree returnsTop Rated Plus
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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
- 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
- PUMA Golf Shorts Boys Small Sand Beige Pockets Chino Preppy Outdoor SportsOpens in a new window or tabPre-Owned$11.97Was: $19.9540% offor Best Offer+$5.95 delivery in 2-4 daysLocated in United StatesFree returnsExtra 20% off with couponTop Rated Plus
- Nike Air Jordan Mesh Shorts Boys Small 8-10 Green Camo Woodland Basketball 8"Opens in a new window or tabPre-Owned$23.00or Best Offer+$4.99 deliveryLocated in United StatesFree returnsTop Rated Plus
- Chubbies Youth Swim Trunks Patriotic Stars Multicolor Pockets Short Small 8/9Opens in a new window or tabNew (Other)$35.89Was: $39.8810% offor Best Offer+$6.71 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+$7.35 deliveryLocated in United StatesFree returns
- Vintage Coogi Jean Shorts Boys JNCO Style Baggy Y2K 90s Skater Sz 14 EmbroideredOpens in a new window or tabPre-Owned$37.50or Best Offer+$5.99 deliveryLocated in United StatesFree returnsTop Rated Plus
- New! Under Armour Shorts Boys 14 Blue Chino Loose Fit ActivewearOpens in a new window or tabBrand New$16.01Was: $22.8730% offor Best Offer+$6.49 deliveryLocated in United StatesFree returnsExtra 20% off with couponTop Rated Plus
- Vineyard Vines Shorts Boys size 14 Seer Sucker Stripe Chino Preppy Yacht SummerOpens in a new window or tabPre-Owned$19.98or Best Offer+$5.99 deliveryLocated in United StatesFree returnsExtra 20% off with couponTop Rated Plus
- GAP Kids Shorts Relaxed Pull on Boys size 14/16 XXL 6.5" Inseam Lot of 2Opens in a new window or tabPre-Owned$25.00or Best Offer+$7.00 deliveryLocated in United StatesFree returns
- 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
- Polo Ralph Lauren Boy’s Size 14 Prepster Blue Denim Jean Shorts Drawstring PonyOpens in a new window or tabPre-Owned$20.97Was: $29.9530% offBuy It Now+$5.80 deliveryLocated in United StatesFree returnsTop Rated Plus
- Cat & Jack Shorts Boys Size S 4/5 Lot Of 2 Blue Beige Cotton Adjustable WaistOpens in a new window or tabBrand New$10.99or Best Offer+$5.31 deliveryLocated in United StatesFree returns
- Gap Boys Madras Shorts 14 Red White Blue Preppy Patriotic 4th of July Black AdjOpens in a new window or tabPre-Owned$12.50or Best Offer+$7.99 deliveryLocated in United StatesFree returnsTop Rated Plus
- Ecko Unltd Kids Jean Shorts & Tee Size 12M Blue Denim Casual Summer Boys NWTOpens in a new window or tabBrand New$23.40Was: $26.0010% offor Best Offer+$10.00 deliveryLocated in United StatesFree returnsTop Rated Plus
- Vintage Y2K Mecca Shorts Boys 14 Raw Blue Jean Denim Stretch Fit Moto StreetwearOpens in a new window or tabPre-Owned$24.99or Best Offer+$6.99 deliveryLocated in United StatesFree returnsExtra 15% off with couponTop Rated Plus
- Polo Ralph Lauren Boy Size 14 Shorts Chino Blue Shorts Classic Flat Front U54Opens in a new window or tabPre-Owned$17.95or Best Offer+$5.95 deliveryLocated in United StatesFree returnsExtra 5% off with couponTop 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
- Nike Shorts Youth Size S 4 6 Mesh Red White Trim Retro Vintage Y2K 2000s PreppyOpens in a new window or tabPre-Owned$19.54Was: $22.9915% offor Best Offer+$8.99 deliveryLocated in United StatesFree returnsExtra 15% off with couponTop Rated Plus
- Old Navy Boys Shorts Size 14 Blue Straight Built in Flex Nantucket Preppy NWTOpens in a new window or tabBrand New$11.99Buy It Now+$5.62 deliveryLocated in United StatesFree returnsTop Rated Plus
- Polo Ralph Lauren Chino Shorts Youth 14 Ivory Minor Flaws Preppy PreownedOpens in a new window or tabPre-Owned$14.99or Best Offer+$7.00 delivery in 2-4 daysLocated in United StatesFree returnsTop Rated Plus
- NWT J Crew Crewcuts Factory Boys Gramercy Shorts 14 Flex Chino Navy BlueOpens in a new window or tabBrand New$20.00or Best Offer+$7.35 deliveryLocated in United StatesFree returnsTop Rated Plus
- VINTAGE Ralph Lauren Polo Shorts Men 14 White Cargo Chino Flap Pockets NWT *Opens in a new window or tabNew (Other)$12.40Was: $16.9927% offor Best Offer+$5.90 deliveryLocated in United StatesFree returnsExtra 25% off with couponTop Rated Plus
- Abercrombie & Fitch Boy's 16 Khaki Shorts Y2K Cut Off Frayed Casual Brown 32x10Opens in a new window or tabPre-Owned$16.99or Best Offer+$8.75 deliveryLocated in United StatesFree returnsTop Rated Plus
- Polo Ralph Lauren Shorts Boys 7 Blue Straight Leg Preppy Casual Pockets CottonOpens in a new window or tabPre-Owned$14.00Was: $20.0030% offor Best Offer+$7.65 deliveryLocated in United StatesFree returnsTop Rated Plus
- Polo Ralph Lauren Shorts Boys 14 25 Red White Blue Plaid 9" Inseam Chino IndiaOpens in a new window or tabPre-Owned$10.41Was: $14.8730% offor Best Offer+$9.99 deliveryLocated in United StatesFree returnsExtra 20% off with couponTop Rated Plus
- Polo Ralph Lauren Bear Ralph's Tigers Drawstring Shorts Preppy Boys Youth Sz 14Opens in a new window or tabPre-Owned$18.00or Best Offer+$5.25 deliveryLocated in United StatesFree returnsTop Rated Plus
- 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
- Jumping Beans Boys Sz 7 Striped Pull On Shorts 100% Cotton PreppyOpens in a new window or tabPre-Owned$5.00or Best Offer+$6.00 deliveryLocated in United StatesFree returnsExtra 10% off with couponTop Rated Plus
- Polo Ralph Lauren Boys Bermuda Shorts Preppy Casual Summer Belted Yellow Sz 14Opens in a new window or tabBrand New$30.79or Best Offer+$5.99 deliveryLocated in United StatesFree returnsTop Rated Plus
- Polo Ralph Lauren Classic Chino Shorts Youth 7 Navy Blue Belted Preppy KidsOpens in a new window or tabPre-Owned$11.69Was: $12.9910% offor Best Offer+$5.50 deliveryLocated in United StatesFree returnsTop Rated Plus
- Vineyard Vines Boy's Size 14 White Cap Stretch 9.5” Breaker ShortsOpens in a new window or tabBrand New$27.99or Best Offer+$7.35 deliveryLocated in United StatesFree returns
- Polo Ralph Lauren Shorts Boys 14 White Cargo Short Classic PreppyOpens in a new window or tabPre-Owned$12.99or Best Offer+$6.25 deliveryLocated in United StatesFree returnsTop Rated Plus
- Polo Ralph Lauren Shorts Boys 7 Blue Chambray Pockets Logo Navy PRL #67 BeltOpens in a new window or tabPre-Owned$19.99or Best Offer+$6.29 deliveryLocated in United StatesFree returnsTop Rated Plus
- Levis Shorts Boys Small Black Slim Fit Chino Drawstring Stretch PreppyOpens in a new window or tabBrand New$17.99or Best Offer+$6.95 deliveryLocated in United StatesFree returnsTop Rated Plus
- 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
- Lucky Brand Shorts Boys Size 14 Tan Chino Flat Front Bermuda Twill StretchOpens in a new window or tabPre-Owned$9.99or Best Offer+$6.99 deliveryLocated in United StatesFree returnsTop Rated Plus
- GAP KIDS SHORTS BOYS SIZE 14 ADJUSTABLE WAISTBAND PLAID PREPPY 2010 BERMUDAOpens in a new window or tabPre-Owned$13.29Was: $18.9930% offor Best Offer+$7.95 deliveryLocated in United StatesFree returnsTop Rated Plus
- Crewcuts Shorts Boy’s Size 2 Cotton Adjustable Waist Preppy - Easter - PurpleOpens in a new window or tabPre-Owned$11.00Buy It NowFree deliveryLocated in United StatesFree returns
- Tommy Hilfiger Shorts Boys Size 14 Olive Green Stretch Preppy ClassicOpens in a new window or tabNew (Other)$14.98or Best Offer+$6.99 deliveryLocated in United StatesFree returnsTop Rated Plus
- 2 Pair Cat&Jack Flat Front Shorts Boys 14 Husky Black School Uniform AdjustableOpens in a new window or tabBrand New$8.99Was: $11.9925% offor Best Offer+$4.99 deliveryLocated in United StatesFree returnsTop Rated Plus
- Polo Ralph Lauren Cargo Shorts Boys 14 Beige Pockets Buckle Casual Loose Baggy*Opens in a new window or tabPre-Owned$9.00Was: $17.9950% offor Best Offer+$6.99 deliveryLocated in United StatesFree returnsTop Rated Plus
- Polo Ralph Lauren Boys Shorts Chino 14 Cotton Mint Green Bermuda Flat FrontOpens in a new window or tabPre-Owned$17.98or Best Offer+$5.95 deliveryLocated in United StatesFree returnsTop Rated Plus
- The Children's Place Boys Plaid Patches Flat Front Classic Chino Shorts Size 6/7Opens in a new window or tabPre-Owned$12.99or Best Offer+$5.99 deliveryLocated in United StatesFree returnsTop Rated Plus
- Polo Ralph Lauren Boys Size 7 Black Cotton Chino Drawstring ShortsOpens in a new window or tabPre-Owned$14.99or Best Offer+$5.10 deliveryLocated in United StatesFree returnsTop Rated Plus
- Vintage Abercrombie & Fitch Shorts Boys Small Green Cargo Surplus Youth KidsOpens in a new window or tabPre-Owned$7.59Was: $18.9860% offor Best Offer+$6.95 deliveryLocated in United StatesFree returnsTop Rated Plus
- Lands End Blue White Striped Seersucker Side Pockets Casual Shorts Size 14Opens in a new window or tabPre-Owned$17.00or Best Offer+$5.12 deliveryLocated in United StatesFree returnsTop Rated Plus
- Garanimals Boys Sz 7 Shorts Gray Checkered Pull On 100% Cotton Preppy SummerOpens in a new window or tabPre-Owned$4.00or Best Offer+$6.00 deliveryLocated in United StatesFree returnsExtra 10% off with couponTop Rated Plus
- VINTAGE Union Bay Cargo Shorts Youth Small White 80s Elastic WaistOpens in a new window or tabBrand New$20.52Was: $22.8010% offor Best Offer+$6.55 deliveryLocated in United StatesFree returns
- Urban Pipeline Shorts Boys Size 14 Pale Yellow Flat Front Adjustable Waist NWTOpens in a new window or tabBrand New$14.99or Best Offer+$6.99 deliveryLocated in United StatesFree returnsExtra 5% off with couponTop Rated Plus
- Polo Ralph Lauren Boys Shorts 14 Bermuda Chino Khaki Tan Pony Logo Flat FrontOpens in a new window or tabPre-Owned$9.80Was: $14.0030% offor Best Offer+$6.99 deliveryLocated in United StatesFree returnsTop Rated Plus
- Janie and Jack Boys 14 Adjustable Cotton Bermuda Short Texture Navy Blue PreppyOpens in a new window or tabPre-Owned$18.95or Best Offer+$6.36 deliveryLocated in United StatesFree returns
- Vineyard Vines Boys Aqua Blue Stretch Chino Shorts Size 14 Adjustable Waist EUCOpens in a new window or tabPre-Owned$16.00Buy It Now+$7.50 deliveryLocated in United StatesFree returns
- 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
- Polo Ralph Lauren Boy Shorts Size 14 Red Blue Madras Plaid Cotton Bermuda PreppyOpens in a new window or tabPre-Owned$12.99or Best Offer+$5.99 deliveryLocated in United StatesFree returnsTop Rated Plus
- VINEYARD VINES Boys Shorts Khakis Chinos Tan SIZE 14 Cotton Blend AdjustableOpens in a new window or tabPre-Owned$17.88or Best Offer+$8.00 deliveryLocated in United StatesFree returns
- HAWK Gray Checkered Preppy Shorts Youth Boys Size 7Opens in a new window or tabPre-Owned$5.40Was: $6.0010% offor Best Offer+$5.50 deliveryLocated in United StatesFree returnsTop Rated Plus
- Beverly Hills Polo Club Cargo Shorts Boys Small Black Pockets Academia PreppyOpens in a new window or tabPre-Owned$4.72or Best Offer+$6.55 deliveryLocated in United StatesFree returns
- Old Navy khaki shorts Boys 14 chino euc tan adjustable Basic CasualOpens in a new window or tabPre-Owned$7.59Was: $7.995% offor Best Offer+$7.35 deliveryLocated in United StatesFree returnsTop Rated Plus
- Vineyard Vines Boys Shorts Size 14 Green 100% Cotton BermudaOpens in a new window or tabPre-Owned$10.99or Best Offer+$5.00 deliveryLocated in United StatesFree returnsTop Rated Plus
- 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
- Pure Stuff Shorts Boys 14 Navy Golf Preppy Church Pockets Cargo Uniform ChinoOpens in a new window or tabPre-Owned$15.99Was: $22.8430% offor Best OfferFree deliveryLocated in United StatesFree returnsTop Rated Plus
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