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- Polo Ralph Lauren Bermuda Shorts Boy's Size 16 Blue Emboidered Flags PreppyOpens in a new window or tabPre-Owned$11.70Was: $13.0010% offor Best Offer+$5.50 delivery in 2-4 daysLocated in United States
- Rip Curl Shorts Boys 23 Gray Chino Outdoors Casual Comfort PreppyOpens in a new window or tabPre-Owned$19.99or Best Offer+$6.99 delivery in 2-4 daysLocated in United StatesFree returnsTop Rated Plus
- Vineyard Vines Shorts Boys 16 White Flat Front Chino PreppyOpens in a new window or tabPre-Owned$18.45or Best Offer+$6.95 deliveryLocated in United StatesFree returnsExtra 20% off with couponTop Rated Plus
- 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
- 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 2-3 daysLocated 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
- 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
- Under Armour Boys Loose Heatgear Shorts Size 16 Gray Pockets Logo Zipper NWTOpens in a new window or tabBrand New$21.95or Best Offer+$3.99 deliveryLocated in United StatesFree returnsTop Rated Plus
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Top selling items from trusted sellers | Sponsored- NWT U.S. Polo Assn Sz16 Rolled Button Cuff Chino Khaki Shorts Adj. Waist UnisexOpens in a new window or tab$12.50light_up_your_life (2,898) 99.9%
- 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 'Whale' Embroidered Club Shorts Flag Blue $59.50 10,14,16Opens in a new window or tab$29.49coachjustyou (2,249) 100%
- Vineyard Vines Boys Gamefish Embroidered Seersucker Shorts Breaker Blue Size 16Opens in a new window or tab$39.00coachjustyou (2,249) 100%
- Vineyard Vines NWT Boy’s Size 16 Blue Embroidered Lacrosse Preppy Cotton ShortsOpens in a new window or tabBrand New$18.00or Best Offer+$7.35 deliveryLocated in United States
- Abercrombie Kids Shorts Boys Size 16 Grey White Checkered Plaid Preppy CottonOpens in a new window or tabPre-Owned$11.00or Best Offer+$4.84 deliveryLocated in United States
- NWT U.S. Polo Assn Sz16 Rolled Button Cuff Chino Khaki Shorts Adj. Waist UnisexOpens in a new window or tabBrand New$12.50Was: $25.0050% offor Best OfferFree delivery in 2-4 daysLocated in United States
- Boys Vineyard Vines Performance Shorts Size 16 Salmon Pink Golf Preppy AthleticOpens in a new window or tabPre-Owned$14.40Was: $18.0020% offBuy It Now+$4.84 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
- 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
- Boys Vineyard Vines Hawaiian Shorts 100% Cotton Size 16 * Large * X Large HawaiiOpens in a new window or tabPre-Owned$19.00or Best Offer+$6.80 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
- 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 delivery in 2-4 daysLocated 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
- 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
- NWT Polo Ralph Lauren PREPSTER PACTHWORK INDIAN MADRAS Plaid Shorts Boys 16 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
- Vineyard Vines Boys Light Khaki Breaker Chino Casual Shorts Adjustable Waist 16Opens in a new window or tabPre-Owned$16.16Was: $17.9510% offor Best Offer+$5.80 deliveryLocated in United States
- 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
- Polo Ralph Lauren Youth Boys Shorts 16 Blue Bib Pony Preppy Old Money CasualOpens in a new window or tabPre-Owned$16.99or Best Offer+$6.99 deliveryLocated in United StatesFree returnsTop Rated Plus
- 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
- 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
- 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
- Levis Cargo Shorts Youth 16 Adjustable waist Khaki Tan Brown Boys Preppy WesternOpens in a new window or tabPre-Owned$21.93or Best Offer+$8.19 deliveryLocated in United StatesFree returnsTop Rated Plus
- Levis Carpenter Shorts Boys 16R Classiccore Blue Denim Normcore PreppyOpens in a new window or tabPre-Owned$9.00or Best Offer+$10.25 deliveryLocated in United States
- Polo Ralph Lauren Boys Shorts 16 Preppy Pink Salmon Cotton Adjustable WaistOpens in a new window or tabPre-Owned$22.64Was: $23.835% offor Best Offer+$5.80 deliveryLocated in United StatesFree returnsExtra 25% off with couponTop Rated Plus
- 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
- 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
- Old Navy Plain Front Khaki Chino Shorts Preppy 12" Inseam - Size Boy's 16Opens in a new window or tabPre-Owned$11.99or Best Offer+$7.35 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 '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 returnsTop Rated Plus
- Vineyard Vines boys shorts sz 16 blue green plaid VV wakehurst club shortsOpens in a new window or tabBrand New$43.21Was: $64.4933% offBuy It Now+$9.45 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 Boy Stretch Breaker Shorts Size 16 Khaki Chino Preppy NewOpens in a new window or tabBrand New$27.99or Best Offer+$6.95 deliveryLocated in United StatesFree returnsTop Rated Plus
- Properly Tied Boys shorts size 16 Salmon Dress Preppy SchoolOpens in a new window or tabPre-Owned$12.08Was: $15.8924% offor Best Offer+$6.55 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
- 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
- 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
- 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
- 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
- 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
- POLO RALPH LAUREN Boys Belted Bermuda Shorts Size 16 Navy Blue NEW Chino UniformOpens in a new window or tabNew (Other)$20.00or Best Offer+$5.95 deliveryLocated in United StatesExtra 15% off with coupon
- 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
- Boys Plaid Bermuda Shorts Gray Cargo Cream Black Adjustable Waist Preppy Size 16Opens in a new window or tabPre-Owned$15.99or Best Offer+$9.25 deliveryLocated in United States
- Vineyard Vines Boys Classic Club | Breaker | Blue Twill Shorts Sz 16Opens in a new window or tabPre-Owned$18.00or Best Offer+$8.71 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
- 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
- Lands End Kids S Small 8 Rust Khaki Striped Shorts Dress Preppy Drawstring ChinoOpens in a new window or tabPre-Owned$14.99or Best Offer+$6.55 deliveryLocated in United States
- Vtg Polo Ralph Lauren Shorts Chino Khaki Boys Size 16 Beige Preppy Golf PonyOpens in a new window or tabPre-Owned$29.99or Best Offer+$10.10 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
- Vineyard Vines pink preppy flat front kids 16 long shortsOpens in a new window or tabPre-Owned$25.00or Best Offer+$7.79 deliveryLocated in United States
- Vineyard Vines Boys Gamefish Embroidered Seersucker Shorts Breaker Blue Size 16Opens in a new window or tabBrand New$39.00Buy It NowFree deliveryLocated in United StatesFree returnsTop Rated Plus
- Columbia Youth Medium Blue Chino Shorts Outdoors Gorpcore Preppy HikingOpens in a new window or tabPre-Owned$14.50Buy It Now+$6.55 deliveryLocated in United States
- Vineyard Vines Blue Embroidered Fish Breaker Shorts size Boy's 16 Coastal PreppyOpens in a new window or tabPre-Owned$28.00or Best Offer+$6.00 deliveryLocated in United States
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