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      • Boys' Clothing (Sizes 4 & Up)
        • Selected categoryShorts
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        SMLXL45678Filter Applied1010-121214Filter Applied161820
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        • Preppy (69) Items (69)
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66 results

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    • PreppyRemove filter
    • Size: 8Remove filter
    • Size: 14Remove filter
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    • HURLEY Boys Plaid Shorts SIZE 8 Navy 100% Cotton Pockets LOGOs
      HURLEY Boys Plaid Shorts SIZE 8 Navy 100% Cotton Pockets LOGOs
      Opens in a new window or tab
      Pre-Owned
      $9.95
      Buy It Now
      +$5.99 delivery
      Sponsored
    • Polo Ralph Lauren Blue Drawstring Preppy Shorts Boy's Size 14
      Polo Ralph Lauren Blue Drawstring Preppy Shorts Boy's Size 14
      Opens in a new window or tab
      Pre-Owned
      $15.00
      or Best Offer
      +$7.00 delivery
      Sponsored
    • Polo Ralph Lauren Shorts Kids Boys Small 8 Navy Blue Fleece Drawstring Preppy
      Polo Ralph Lauren Shorts Kids Boys Small 8 Navy Blue Fleece Drawstring Preppy
      Opens in a new window or tab
      Pre-Owned
      $18.00
      or Best Offer
      +$7.65 delivery
      Free returns
      Sponsored
      Top Rated Plus
    • J.Crew Boys Crewcuts Active Shorts Size 8 Brown Tan Outdoors Training Preppy
      J.Crew Boys Crewcuts Active Shorts Size 8 Brown Tan Outdoors Training Preppy
      Opens in a new window or tab
      Pre-Owned
      $20.99
      Buy It Now
      +$4.84 delivery
      Sponsored
    • Vineyard Vines Boys 14 Plaid Shorts Blue Green Shep Ian Preppy 100% Cotton
      Vineyard Vines Boys 14 Plaid Shorts Blue Green Shep Ian Preppy 100% Cotton
      Opens in a new window or tab
      Pre-Owned
      $16.00
      or Best Offer
      +$4.84 delivery
      Sponsored
    • Vineyard Vines Seersucker Shorts Size 14 Boy Spring Summer Country Club Preppy
      Vineyard Vines Seersucker Shorts Size 14 Boy Spring Summer Country Club Preppy
      Opens in a new window or tab
      Pre-Owned
      $22.50
      or Best Offer
      +$8.71 delivery
      Sponsored
    • Vineyard Vines Boys Kids 14 Blue Uniform Dress Shep Ian Chino Adjustable Waist
      Vineyard Vines Boys Kids 14 Blue Uniform Dress Shep Ian Chino Adjustable Waist
      Opens in a new window or tab
      Pre-Owned
      $7.95
      Buy It Now
      +$5.95 delivery
      Sponsored
    • IZOD Boys Plaid Shorts SIZE 8 Blue Adjustable Waist 100% Cotton Pockets
      IZOD Boys Plaid Shorts SIZE 8 Blue Adjustable Waist 100% Cotton Pockets
      Opens in a new window or tab
      Pre-Owned
      $9.95
      Buy It Now
      +$5.99 delivery
      Sponsored
    • Ralph Lauren Boys Size 14 Bermuda Shorts Pink Plaid Preppy Easter Beach Golf
      Ralph Lauren Boys Size 14 Bermuda Shorts Pink Plaid Preppy Easter Beach Golf
      Opens in a new window or tab
      Pre-Owned
      $12.17
      Was: $13.9913% off
      Buy It Now
      +$7.01 delivery
      Sponsored
    • Vintage Red Gap Kids Cargo Shorts size 8 Spring 2004 Line Y2K Preppy
      Vintage Red Gap Kids Cargo Shorts size 8 Spring 2004 Line Y2K Preppy
      Opens in a new window or tab
      Pre-Owned
      $15.00
      or Best Offer
      +$4.54 delivery
      Sponsored
    • Vineyard Vines Boys 'Whale' Embroidered Club Shorts Flag Blue $59.50 10,14,16
      Vineyard Vines Boys 'Whale' Embroidered Club Shorts Flag Blue $59.50 10,14,16
      Opens in a new window or tab
      Brand New
      $29.49
      Buy It Now
      Free delivery
      Free returns
      4+ watchers
      Sponsored
      Top Rated Plus
    • NWT Crewcuts Boy’s Stanton Seersucker Chino Shorts Blue White Striped Cotton 14
      NWT Crewcuts Boy’s Stanton Seersucker Chino Shorts Blue White Striped Cotton 14
      Opens in a new window or tab
      Brand New
      $19.99
      Was: $39.9950% off
      or Best Offer
      +$7.35 delivery
      Free returns
      Sponsored
    • Polo Ralph Lauren Cargo Shorts Little Boys 8 Green Utility Casual Preppy Pockets
      Polo Ralph Lauren Cargo Shorts Little Boys 8 Green Utility Casual Preppy Pockets
      Opens in a new window or tab
      Pre-Owned
      $28.00
      or Best Offer
      +$7.65 delivery
      Free returns
      Sponsored
      Top Rated Plus
    • Crewcuts Boys Pink and Blue Striped Bermuda Seersucker Shorts Size 14
      Crewcuts Boys Pink and Blue Striped Bermuda Seersucker Shorts Size 14
      Opens in a new window or tab
      Pre-Owned
      $15.00
      or Best Offer
      +$5.80 delivery
      Free returns
      Sponsored
    • Vineyard Vines Shorts Boys Size 14 Beige Chino Casual Preppy Stretch Logo
      Vineyard Vines Shorts Boys Size 14 Beige Chino Casual Preppy Stretch Logo
      Opens in a new window or tab
      Pre-Owned
      $19.99
      or Best Offer
      +$5.95 delivery
      Free returns
      Sponsored
      Top Rated Plus
    • Hannah Andersson Terry cloth shorts boys 8 pull on drawstring beach summer
      Hannah Andersson Terry cloth shorts boys 8 pull on drawstring beach summer
      Opens in a new window or tab
      Pre-Owned
      $11.04
      Was: $12.9915% off
      Buy It Now
      +$4.84 delivery
      Sponsored
    • Castaway Nantucket Boys Size 8 Hot Dog Hamburger Shorts BarBQ Preppy Embroidery
      Castaway Nantucket Boys Size 8 Hot Dog Hamburger Shorts BarBQ Preppy Embroidery
      Opens in a new window or tab
      Pre-Owned
      $19.99
      Buy It Now
      +$5.95 delivery
      Sponsored
    • Polo Ralph Lauren Boys White Blue Embroidered Preppie Chino Shorts Size 8 NWT
      Polo Ralph Lauren Boys White Blue Embroidered Preppie Chino Shorts Size 8 NWT
      Opens in a new window or tab
      Brand New
      $27.00
      Was: $45.0040% off
      Buy It Now
      +$4.84 delivery
      Free returns
      Extra 20% off with coupon
      Sponsored
    • Polo Ralph Lauren Boys Chino Shorts Navy Blue NWT Size 14 Youth Kids Preppy
      Polo Ralph Lauren Boys Chino Shorts Navy Blue NWT Size 14 Youth Kids Preppy
      Opens in a new window or tab
      Brand New
      $19.95
      Buy It Now
      +$4.84 delivery
      Sponsored
    • Vineyard Vines Boys Size 14 Green Breaker Shorts Uniform School Preppy Nautical
      Vineyard Vines Boys Size 14 Green Breaker Shorts Uniform School Preppy Nautical
      Opens in a new window or tab
      Pre-Owned
      $10.00
      Buy It Now
      +$5.49 delivery
      Extra 20% off with coupon
      Sponsored
    • Pantagonia Boys Fitz Stripe Board Shorts Swim Trunks Size 14 Beach Preppy Active
      Pantagonia Boys Fitz Stripe Board Shorts Swim Trunks Size 14 Beach Preppy Active
      Opens in a new window or tab
      Pre-Owned
      $18.00
      or Best Offer
      +$4.71 delivery
      Sponsored
    • The Children's Place Boys Khaki Navy Cargo Pull On Adjustable Shorts Sz 14 Husky
      The Children's Place Boys Khaki Navy Cargo Pull On Adjustable Shorts Sz 14 Husky
      Opens in a new window or tab
      Pre-Owned
      $19.99
      or Best Offer
      +$10.00 delivery
      Sponsored
    • Nwt CLASS CLUB Dillard's MODERN FIT Boy's BLUE Stretch Twill CHINO Shorts Sz 14
      Nwt CLASS CLUB Dillard's MODERN FIT Boy's BLUE Stretch Twill CHINO Shorts Sz 14
      Opens in a new window or tab
      Brand New
      $10.80
      Was: $12.0010% off
      Buy It Now
      +$6.62 delivery
      Sponsored
    • Polo Ralph Lauren Shorts Boys 14 Brown Tan Chino Preppy Casual Kids Youth
      Polo Ralph Lauren Shorts Boys 14 Brown Tan Chino Preppy Casual Kids Youth
      Opens in a new window or tab
      Pre-Owned
      $15.00
      or Best Offer
      Free delivery
      Sponsored
    • EUC Vineyard Vines Boys Size 14 Classic Bermuda Shorts Blue Embroidered Lacrosse
      EUC Vineyard Vines Boys Size 14 Classic Bermuda Shorts Blue Embroidered Lacrosse
      Opens in a new window or tab
      Pre-Owned
      $14.95
      or Best Offer
      +$6.90 delivery in 2-4 days
      Sponsored
    • NWT Gap Kids Navy Blue Cargo Shorts Adjustable Tab Waist Size 8
      NWT Gap Kids Navy Blue Cargo Shorts Adjustable Tab Waist Size 8
      Opens in a new window or tab
      Brand New
      $15.99
      or Best Offer
      +$6.55 delivery
      Sponsored
    • Polo Ralph Lauren Boys Blue Chino Shorts Flat Front Sz 14 Preppy Coastal
      Polo Ralph Lauren Boys Blue Chino Shorts Flat Front Sz 14 Preppy Coastal
      Opens in a new window or tab
      Pre-Owned
      $14.00
      or Best Offer
      +$4.99 delivery
      Sponsored
    • Vineyard Vines Boys Lobster Print Shorts Navy Blue & Red Size Size 14 Immaculate
      Vineyard Vines Boys Lobster Print Shorts Navy Blue & Red Size Size 14 Immaculate
      Opens in a new window or tab
      Pre-Owned
      $18.50
      or Best Offer
      +$7.35 delivery
      Sponsored
    • Vineyard Vines Boys Cotton Summer Twill Club Shorts Antigua Green (14)  $59.50
      Vineyard Vines Boys Cotton Summer Twill Club Shorts Antigua Green (14) $59.50
      Opens in a new window or tab
      Brand New
      $29.50
      Buy It Now
      Free delivery
      Free returns
      Sponsored
      Top Rated Plus
    • Vineyard Vines Boys Seersucker Breaker Shorts Size 8
      Vineyard Vines Boys Seersucker Breaker Shorts Size 8
      Opens in a new window or tab
      Pre-Owned
      $18.00
      or Best Offer
      +$9.45 delivery
      Sponsored
    • Vineyard Vines Coral Bermuda Boys Kids Shorts Preppy 14 323 Preppy
      Vineyard Vines Coral Bermuda Boys Kids Shorts Preppy 14 323 Preppy
      Opens in a new window or tab
      Pre-Owned
      $12.95
      Buy It Now
      +$6.00 delivery
      Sponsored
    • Vineyard Vines Boys 'Whale' Embroidered Club Shorts Stone $59.50 Size 12 nd 14
      Vineyard Vines Boys 'Whale' Embroidered Club Shorts Stone $59.50 Size 12 nd 14
      Opens in a new window or tab
      Brand New
      $29.49
      Buy It Now
      Free delivery
      Free returns
      Sponsored
      Top Rated Plus
    • NWT Tailor Vintage Boys Pineapple Bermuda Shorts 8 Resortwear
      NWT Tailor Vintage Boys Pineapple Bermuda Shorts 8 Resortwear
      Opens in a new window or tab
      Brand New
      $22.99
      or Best Offer
      +$5.00 delivery
      Sponsored
    • NWT BELLA BLISS Boys Sz 8 Blue Wide Oxford Striped Play Shorts Preppy
      NWT BELLA BLISS Boys Sz 8 Blue Wide Oxford Striped Play Shorts Preppy
      Opens in a new window or tab
      Brand New
      $15.99
      or Best Offer
      +$6.00 delivery
      Sponsored
    • Crewcuts Blue Chino Khaki Shorts Preppy 7" Inseam - Size Boy's 8
      Crewcuts Blue Chino Khaki Shorts Preppy 7" Inseam - Size Boy's 8
      Opens in a new window or tab
      Pre-Owned
      $9.99
      or Best Offer
      +$6.55 delivery
      Sponsored
    • Kids Crown & Ivy Navy Flat Front Adjustable Shorts Size 14 Preppy Uniform Church
      Kids Crown & Ivy Navy Flat Front Adjustable Shorts Size 14 Preppy Uniform Church
      Opens in a new window or tab
      Pre-Owned
      $5.95
      or Best Offer
      +$5.80 delivery
      Sponsored
    • Vineyard Vines Boys Light Baby Blue Preppy Casual Chino Cotton Shorts Size 14
      Vineyard Vines Boys Light Baby Blue Preppy Casual Chino Cotton Shorts Size 14
      Opens in a new window or tab
      Pre-Owned
      $22.00
      or Best Offer
      +$5.99 delivery
      Sponsored
    • Lot Of 2 Old Navy Boys School Uniform Pants, Khaki Flat Front Adjustable Size 14
      Lot Of 2 Old Navy Boys School Uniform Pants, Khaki Flat Front Adjustable Size 14
      Opens in a new window or tab
      Pre-Owned
      $12.00
      Buy It Now
      +$11.07 delivery
      Sponsored
    • Vineyard Vines Kids Boys Cotton Summer Twill Club Shorts Starboard Green  $59.50
      Vineyard Vines Kids Boys Cotton Summer Twill Club Shorts Starboard Green $59.50
      Opens in a new window or tab
      Brand New
      $34.49
      Buy It Now
      Free delivery
      Free returns
      Sponsored
      Top Rated Plus
    • Children's Place Burnt Orange/Red Boys Chino Shorts Size 8 Stylish Preppy
      Children's Place Burnt Orange/Red Boys Chino Shorts Size 8 Stylish Preppy
      Opens in a new window or tab
      Pre-Owned
      $12.99
      or Best Offer
      +$4.84 delivery
      Sponsored
    • Gymboree boys 8 madras preppy plaid Bermuda shorts blue yellow summer bright
      Gymboree boys 8 madras preppy plaid Bermuda shorts blue yellow summer bright
      Opens in a new window or tab
      Pre-Owned
      $20.00
      or Best Offer
      +$7.35 delivery
      Sponsored
    • Zara Blue Flat Front Shorts Boys Size 8 Linen Blend Preppy Casual Summer Coastal
      Zara Blue Flat Front Shorts Boys Size 8 Linen Blend Preppy Casual Summer Coastal
      Opens in a new window or tab
      Pre-Owned
      $16.00
      or Best Offer
      +$14.25 delivery
      Sponsored
    • Vineyard Vines Shep & Ian Boys 14 Chino Shorts Light Blue Preppy Shorts Golf
      Vineyard Vines Shep & Ian Boys 14 Chino Shorts Light Blue Preppy Shorts Golf
      Opens in a new window or tab
      Pre-Owned
      $22.00
      or Best Offer
      Free delivery
      Sponsored
    • Vineyard Vines Boys 'Whale' Embroidered Club Shorts Salmon
      Vineyard Vines Boys 'Whale' Embroidered Club Shorts Salmon
      Opens in a new window or tab
      Pre-Owned
      $24.95
      Buy It Now
      +$9.45 delivery
      Sponsored
    • Vtg Polo Ralph Lauren Shorts Chino Khaki Boys Size 14 Beige Preppy Golf Pony
      Vtg Polo Ralph Lauren Shorts Chino Khaki Boys Size 14 Beige Preppy Golf Pony
      Opens in a new window or tab
      Pre-Owned
      $19.99
      or Best Offer
      +$10.10 delivery
      Sponsored
    • Vineyard Vines Bermuda Shorts Boys Youth Size 14 Beige VERY GOOD
      Vineyard Vines Bermuda Shorts Boys Youth Size 14 Beige VERY GOOD
      Opens in a new window or tab
      Pre-Owned
      $7.99
      Was: $9.9920% off
      Buy It Now
      +$7.00 delivery
      Sponsored
    • Vineyard Vines Breaker Shorts Blue Twill Cotton Casual Stretch Youth Boys 14
      Vineyard Vines Breaker Shorts Blue Twill Cotton Casual Stretch Youth Boys 14
      Opens in a new window or tab
      Brand New
      $49.99
      Buy It Now
      +$6.99 delivery
      Sponsored
    • Polo Ralph Lauren Denim Shorts Jorts  100% Cotton  10" Inseam Preppy Boys 14
      Polo Ralph Lauren Denim Shorts Jorts 100% Cotton 10" Inseam Preppy Boys 14
      Opens in a new window or tab
      Pre-Owned
      $19.98
      or Best Offer
      +$5.62 delivery
      Free returns
      Sponsored
      Top Rated Plus
    • Gap Kids Boys Pull On Elastic Waistband Front & Back Pockets Stretch Shorts
      Gap Kids Boys Pull On Elastic Waistband Front & Back Pockets Stretch Shorts
      Opens in a new window or tab
      Brand New
      $12.00
      or Best Offer
      +$6.20 delivery
      Sponsored
    • NWT There Abouts Boys Size 14 Lexington Light Green Chino Shorts MSRP $32
      NWT There Abouts Boys Size 14 Lexington Light Green Chino Shorts MSRP $32
      Opens in a new window or tab
      Brand New
      $19.99
      Buy It Now
      +$5.71 delivery
      Sponsored
    • Tailor Vintage Boys Size 14 Pink Bermuda Shorts
      Tailor Vintage Boys Size 14 Pink Bermuda Shorts
      Opens in a new window or tab
      Pre-Owned
      $9.25
      or Best Offer
      +$6.99 delivery
      Sponsored
    • NWT Gap Boy's Elastic Waistband Stretch Soft Twill Shorts Size M (8) Blue
      NWT Gap Boy's Elastic Waistband Stretch Soft Twill Shorts Size M (8) Blue
      Opens in a new window or tab
      Brand New
      $19.99
      or Best Offer
      Free delivery
      Sponsored
    • Boys Vineyard Vines Club Khaki Golf Shorts 3H0141- Size 14
      Boys Vineyard Vines Club Khaki Golf Shorts 3H0141- Size 14
      Opens in a new window or tab
      Pre-Owned
      $9.97
      or Best Offer
      +$4.71 delivery
      Sponsored
    • White Blue Striped Preppy Shorts Boy’s 8 Adjustable Waist Lightweight Fall trend
      White Blue Striped Preppy Shorts Boy’s 8 Adjustable Waist Lightweight Fall trend
      Opens in a new window or tab
      Pre-Owned
      $18.00
      or Best Offer
      +$9.45 delivery
      Sponsored
    • Vtg Polo Ralph Lauren Shorts Chino Khaki Boys Size 14 Navy Blue Preppy Golf Pony
      Vtg Polo Ralph Lauren Shorts Chino Khaki Boys Size 14 Navy Blue Preppy Golf Pony
      Opens in a new window or tab
      Pre-Owned
      $19.99
      or Best Offer
      +$10.10 delivery
      Sponsored
    • Lot Of 2 Old Navy Boys School Uniform Pants, Khaki Flat Front Adjustable Size 14
      Lot Of 2 Old Navy Boys School Uniform Pants, Khaki Flat Front Adjustable Size 14
      Opens in a new window or tab
      Pre-Owned
      $12.00
      Buy It Now
      +$11.07 delivery
      Sponsored
    • Gap Kid Boy Pull On Elastic Waistband Front Back Pocket Soft Twill Green Sz 8 L5
      Gap Kid Boy Pull On Elastic Waistband Front Back Pocket Soft Twill Green Sz 8 L5
      Opens in a new window or tab
      Brand New
      $6.99
      Buy It Now
      +$5.99 delivery
      Free returns
      Sponsored
    • Zara boys checkered shorts with rope tie and pockets. Preppy shorts sz 8 128cm
      Zara boys checkered shorts with rope tie and pockets. Preppy shorts sz 8 128cm
      Opens in a new window or tab
      Pre-Owned
      $16.00
      or Best Offer
      +$14.25 delivery
      Sponsored
    • Abercrombie & Fitch Gingham Plaid Shorts Boys Size 14 Blue White Bermuda Preppy
      Abercrombie & Fitch Gingham Plaid Shorts Boys Size 14 Blue White Bermuda Preppy
      Opens in a new window or tab
      Pre-Owned
      $24.99
      or Best Offer
      Free delivery
      Free returns
      Sponsored
    • Vineyard Vines Shorts Boys 14 Blue Embroidered Lacrosse Lax Casual Preppy Cotton
      Vineyard Vines Shorts Boys 14 Blue Embroidered Lacrosse Lax Casual Preppy Cotton
      Opens in a new window or tab
      Pre-Owned
      $8.00
      Was: $10.0020% off
      or Best Offer
      +$4.80 delivery
      Sponsored
    • White Blue Striped Preppy Shorts Boy’s 8 Adjustable Waist Lightweight Fall trend
      White Blue Striped Preppy Shorts Boy’s 8 Adjustable Waist Lightweight Fall trend
      Opens in a new window or tab
      Pre-Owned
      $15.00
      or Best Offer
      +$9.45 delivery
      Sponsored
    • Gap Kid Boy Pull On Elastic Waistband Front Back Pockets Soft Twill Navy Sz 8 L5
      Gap Kid Boy Pull On Elastic Waistband Front Back Pockets Soft Twill Navy Sz 8 L5
      Opens in a new window or tab
      Brand New
      $6.99
      Buy It Now
      +$5.99 delivery
      Free returns
      Sponsored
    • Vineyard Vines Shorts Boys Size 14 Beige Chino Casual Preppy Stretch Logo
      Vineyard Vines Shorts Boys Size 14 Beige Chino Casual Preppy Stretch Logo
      Opens in a new window or tab
      Pre-Owned
      $15.00
      Buy It Now
      +$5.62 delivery
      Sponsored
    • Children's Place Blue White Stripe Palm Tree Boys Chino Shorts Size 8 Preppy
      Children's Place Blue White Stripe Palm Tree Boys Chino Shorts Size 8 Preppy
      Opens in a new window or tab
      Pre-Owned
      $12.99
      or Best Offer
      +$4.84 delivery
      Sponsored
    • Buffalo David Bitton Boys Denim Parker Jean Shorts Fray Hem Distressed SZ 14
      Buffalo David Bitton Boys Denim Parker Jean Shorts Fray Hem Distressed SZ 14
      Opens in a new window or tab
      Pre-Owned
      $23.00
      or Best Offer
      +$7.50 delivery
      Sponsored
    • URBAN PIPELINE youth size 14 plaid bermuda shorts walking tan preppy beige surf
      URBAN PIPELINE youth size 14 plaid bermuda shorts walking tan preppy beige surf
      Opens in a new window or tab
      Pre-Owned
      $11.99
      Buy It Now
      Free delivery
      Sponsored
    • Vineyard Vines Seersucker Boat Embroidered Shorts Boys 14 Adjustable Waist
      Vineyard Vines Seersucker Boat Embroidered Shorts Boys 14 Adjustable Waist
      Opens in a new window or tab
      Pre-Owned
      $20.00
      or Best Offer
      +$6.55 delivery
      Sponsored
    • Lands End Kids S Small 8 Rust Khaki Striped Shorts Dress Preppy Drawstring Chino
      Lands End Kids S Small 8 Rust Khaki Striped Shorts Dress Preppy Drawstring Chino
      Opens in a new window or tab
      Pre-Owned
      $14.99
      or Best Offer
      +$6.55 delivery
      Sponsored
    • Vineyard Vines Boys Summer Twill Breaker Blue Adjustable Waist Shorts Size 14
      Vineyard Vines Boys Summer Twill Breaker Blue Adjustable Waist Shorts Size 14
      Opens in a new window or tab
      Pre-Owned
      $16.00
      or Best Offer
      +$9.84 delivery
      Sponsored
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