183 results
- Under Armour Boys Plaid Chino Shorts Size Small Blue Preppy GolfOpens in a new window or tabPre-Owned$12.71Was: $14.9515% offor Best Offer+$5.50 delivery
- Polo Ralph Lauren Blue Drawstring Preppy Shorts Boy's Size 14Opens in a new window or tabPre-Owned$15.00or Best Offer+$7.00 deliveryExtra 15% off with coupon
- 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
- Lacoste Boys Two Tone White/ Olive Green Logo Sweat Shorts W/Pockets Kids Sz 10Opens in a new window or tabPre-Owned$25.00or Best Offer+$8.54 delivery
- 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 deliveryFree returnsExtra 10% off with couponTop Rated Plus
- 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 deliveryFree returnsTop Rated Plus
- 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 deliveryFree returnsTop Rated Plus
- 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 delivery
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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$15.00light_up_your_life (2,839) 99.9%
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- Crewcuts Factory Pink Shorts Boy’s Size 10 Cotton Adjustable Waist Preppy EasterOpens in a new window or tabPre-Owned$20.00or Best Offer+$6.99 delivery
- Tommy Hilfiger Boys Sz 20 Shorts Blue Flat Front Chino 100% Cotton Preppy SummerOpens in a new window or tabPre-Owned$8.00or Best Offer+$7.00 deliveryFree returnsExtra 10% off with couponTop Rated Plus
- Polo Ralph Lauren Boys Size 12 White Cotton Bermuda Shorts Preppy YouthOpens in a new window or tabPre-Owned$25.00or Best Offer+$7.99 delivery
- Vineyard Vines NWT Boy’s Size 16 Blue Embroidered Lacrosse Preppy Cotton ShortsOpens in a new window or tabBrand New$19.00or Best Offer+$7.35 delivery
- Polo Ralph Lauren Boys Prepster Shorts Sz 14 Chambray BlueOpens in a new window or tabPre-Owned$18.00or Best Offer+$9.91 delivery
- 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
- Vineyard Vines Performance Shorts Boys 16 Pink BreathableOpens in a new window or tabPre-Owned$11.62or Best Offer+$5.99 deliveryFree returnsTop Rated Plus
- Rip Curl Shorts Boys 23 Gray Chino Outdoors Casual Comfort PreppyOpens in a new window or tabPre-Owned$13.99Was: $19.9930% offor Best Offer+$6.99 delivery in 2-4 daysFree returnsExtra 15% off with couponTop Rated Plus
- Vineyard Vines Boys Light Khaki Breaker Chino Casual Shorts Adjustable Waist 16Opens in a new window or tabPre-Owned$17.95or Best Offer+$5.80 delivery
- Abercrombie Kids Shorts Boys Size 16 Grey White Checkered Plaid Preppy CottonOpens in a new window or tabPre-Owned$12.49or Best Offer+$4.84 delivery
- Properly Tied Boys shorts size 16 Salmon Dress Preppy SchoolOpens in a new window or tabPre-Owned$12.24Was: $15.8923% offor Best Offer+$6.55 delivery
- NEW Gap Kids Boys 12 Husky Green Shorts Cotton Spandex Summer Kids PocketsOpens in a new window or tabBrand New$19.99or Best Offer+$9.45 delivery
- Strasburg Boys Shorts Size 5 Solid White Dress Preppy NEWOpens in a new window or tabBrand New$20.00or Best Offer+$7.31 delivery
- NEW Boys La Jenns 4T Brown Gingham Shorts PreppyOpens in a new window or tabBrand New$12.00or Best Offer+$4.50 deliveryExtra 30% off with coupon
- Janie & Jack Boys’ Linen Blend Shorts Blue Chambray Size 14 Stretch WaistOpens in a new window or tabPre-Owned$17.00or Best Offer+$4.41 delivery in 2-4 days
- Ralph Lauren Polo Youth XL 18-20 Golf Athleisure Shirt Preppy Sporty ClassiccoreOpens in a new window or tabPre-Owned$10.00or Best Offer+$5.95 delivery
- 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 delivery
- 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 delivery
- Polo Ralph Lauren Boys Kids Stretch Twill Cargo Shorts Tan Khaki Size 12Opens in a new window or tabPre-Owned$17.99or Best Offer+$7.95 delivery
- Murrays Toggery Shop Boys Sz 10 Shorts Nantucket Reds Cotton Adjustable WaistOpens in a new window or tabPre-Owned$14.40Was: $24.0040% offor Best OfferFree deliveryFree returnsTop Rated Plus
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- Polo Ralph Lauren Navy Blue Boy 10 Blue Pony Preppy Parachute Rugby Twill ShortsOpens in a new window or tabPre-Owned$10.79Was: $11.9910% offor Best Offer+$6.95 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
- Polo by Ralph Lauren Boys Navy Blue Flat Front Cotton Chino Shorts 6X PreppyOpens in a new window or tabPre-Owned$25.00or Best Offer+$6.40 delivery
- Vineyard Vines by Shep & Ian Boys 12 Khaki Stretch Breaker Shorts Uniform PreppyOpens in a new window or tabPre-Owned$9.00or Best Offer+$5.49 delivery
- J Crew CrewCuts Chino Shorts Boys Size 12 Pink Preppy Casual Southern BreathableOpens in a new window or tabBrand New$19.66Was: $21.8510% offor Best Offer+$7.35 delivery
- Janie and Jack Boys Size 4 Linen Cotton Pink Chino Shorts EasterOpens in a new window or tabPre-Owned$8.99or Best Offer+$5.10 deliveryFree returnsTop Rated Plus
- Orient Expressed Vintage Boys Checked Shorts Sz 6 Easter Blue And Green PreppyOpens in a new window or tabPre-Owned$7.28or Best Offer+$5.75 delivery
- Polo Ralph Lauren Linen Blend Preppy Pink Flat Front Little Boy Shorts - Size 3Opens in a new window or tabPre-Owned$15.00or Best Offer+$4.99 delivery
- 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
- Polo Ralph Lauren Shorts Boys Sz 10 Chino Khaki CasualOpens in a new window or tabPre-Owned$15.25or Best Offer+$6.80 deliveryFree returnsTop Rated Plus
- Lot Of 2 Gap Kids Boys Pull On Elastic Waist w/ Pockets Twill XL (14/16) GreenOpens in a new window or tabBrand New$20.99Was: $29.9930% offor Best Offer+$5.80 delivery
- Abercrombie Kids Khaki Shorts Sz 12 Board Skater Vintage Preppy Teen Tween Y2KOpens in a new window or tabPre-Owned$7.99Was: $15.9950% offor Best Offer+$9.25 delivery
- Gap Kids Boys Size 4 Madras Patchwork Plaid Adjustable Waist ShortsOpens in a new window or tabPre-Owned$8.99or Best Offer+$5.60 deliveryFree returnsTop Rated Plus
- N.W.D Gap Kids Boys Stretch Twill Shorts, Medieval Blue, Size L (10/12)Opens in a new window or tabNew (Other)$15.29Was: $16.9910% offor Best OfferFree delivery
- Polo Ralph Lauren Kids Shorts Toddler 4T Green Cotton PreppyOpens in a new window or tabPre-Owned$15.99or Best Offer+$4.84 delivery
- Polo Ralph Lauren Shirt Boys Size XL (18-20) Blue Striped Preppy Red Pony GolfOpens in a new window or tabPre-Owned$18.00or Best Offer+$6.00 deliveryExtra 15% off with coupon
- 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 delivery
- NWT Janie And Jack Linen Cotton Shorts 6 Boys Stripe Blue Adjustable WaistOpens in a new window or tabBrand New$17.99or Best Offer+$5.25 delivery
- Vineyard Vines Boys Size 12 Chino Shorts Breaker blue Pineapple PrintOpens in a new window or tabPre-Owned$24.00or Best Offer+$4.84 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
- GAP Kids Gray Seersucker Shorts, Size Small 6/7, NEWOpens in a new window or tabBrand New$12.99or Best Offer+$5.31 delivery
- Janie and Jack Boys Size 7 / Plaid Short, adjustable waist, Field Green and NavyOpens in a new window or tabPre-Owned$8.99or Best Offer+$4.99 delivery in 2-4 days
- Polo Ralph Lauren Boy’s Size 10 Blue and White Seersucker ShortsOpens in a new window or tabPre-Owned$19.20Was: $24.0020% offor Best Offer+$8.00 delivery
- Vineyard Vines Performance Breaker Shorts Chinos Boys 10 Khaki Flat Front PreppyOpens in a new window or tabPre-Owned$11.99or Best Offer+$6.99 delivery
- Vineyard Vines Breaker Shorts Boys Island Paradice green blue 10 NWTOpens in a new window or tabBrand New$19.00Time left1d 2hor Best Offer+$4.99 delivery
- Lot Of 2 Gap Kids Boys Pull On Elastic Waist w/ Pockets Twill L (10/12) BlueOpens in a new window or tabBrand New$20.99Was: $29.9930% offor Best Offer+$5.80 delivery
- Carters Kids Size 4 Chino Short Blue Adjustable Waist Casual Stretch PreppyOpens in a new window or tabBrand New$12.15or Best Offer+$5.62 deliveryExtra 20% off with coupon
- GapKids Cotton Cargo Patchwork Madras Boys Shorts size 10Opens in a new window or tabPre-Owned$19.98or Best Offer+$7.80 deliveryFree returns
- Levis Cargo Shorts Youth 16 Adjustable waist Khaki Tan Brown Boys Preppy WesternOpens in a new window or tabPre-Owned$17.54Was: $21.9320% offor Best Offer+$8.19 deliveryFree returnsTop Rated Plus
- Vineyard Vines by Shep & Ian Boys Coral Chino Shorts Size 18Opens in a new window or tabPre-Owned$9.95or Best Offer+$5.85 delivery
- 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 U.S. Polo Assn Sz16 Rolled Button Cuff Chino Khaki Shorts Adj. Waist UnisexOpens in a new window or tabBrand New$15.00Was: $25.0040% offor Best OfferFree delivery in 2-4 days
- Gap Boy's Elastic Waistband Front & Back Pockets Stretch Soft Twill Shorts 10/12Opens in a new window or tabBrand New$12.59Was: $17.9930% offor Best OfferFree delivery
- NEW Tucker + Tate Boy's Size 10/12 Pull On 9" Chino Shorts in Blue StonewashOpens in a new window or tabBrand New$19.99or Best Offer+$5.99 delivery in 2-4 days
- Nautica XLarge 7x Boys Shorts Orange And Blue Dress Summer PreppyOpens in a new window or tabPre-Owned$15.00or Best Offer+$5.99 delivery
- J.Crew Crewcuts BOYS GRAMERCY COTTON DINO SHORT, Size 4, imperial Blue GreenOpens in a new window or tabPre-Owned$15.85Was: $18.9516% offor Best Offer+$6.55 delivery
- 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 delivery
- O'Neill Hybrid Heathered Blue Boys Shorts Size 24 Casual Golf Preppy SummerOpens in a new window or tabPre-Owned$15.00or Best Offer+$14.25 delivery
- POLO Ralph Lauren Seersucker Shorts Preppy Blue White - Size Boy's 18Opens in a new window or tabPre-Owned$14.99or Best Offer+$7.35 delivery
- Polo Ralph Lauren Conductor Engineer Shorts Striped Cotton Retro Boys Size 20Opens in a new window or tabPre-Owned$19.99or Best Offer+$6.84 delivery
- NWT Childrens Place Boys Preppy Plaid Shorts Size 7Opens in a new window or tabBrand New$10.50or Best Offer+$4.50 delivery
- Polo Ralph Lauren Pink Preppy Bermuda Long Shorts boys 18Opens in a new window or tabPre-Owned$22.00or Best Offer+$8.90 delivery
- NWT CREWCUTS CHINO SHORTS BOYS SIZE 4 YELLOW SPRING EASTEROpens in a new window or tabBrand New$12.99Was: $19.9935% offor Best Offer+$6.95 deliveryFree returns
- Penguin By Munsingweart Navy Blue Preppy Cotton Chino Shorts Boys Size 12Opens in a new window or tabPre-Owned$8.39Was: $11.9930% offor Best Offer+$4.84 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
- Brooks Brothers Shorts Youth Boy 18 Patchwork Plaid Cotton 28x10 Preppy AcademiaOpens in a new window or tabPre-Owned$18.33Was: $26.1830% offor Best Offer+$5.26 delivery
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