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preppy clothing (2,000 RESULTS)

This preppy rugby-inspired cotton bib features a bold striped design and our signature embroidered pony at the front. Shoulder straps secure at the back of the neck with a snapped closure.... Layette Banner Rugby Bib

Layette Banner Rugby Bib

Ralph Lauren
Ralph Lauren
$10.00 $7.99

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CLOSEOUTS . Once the uniform of the preppy class, madras goes mainstream in Gramicciand#39;s Jalama Paya Madras shirt, an expressively colored plaid in soft, garment-washed cotton with... Gramicci Jalama Paya Madras Shirt - Short Sleeve (For Men) ? ELM

Gramicci Jalama Paya Madras Shirt -...

Sierra Trading Post
$58.00 $39.95

31%

Off

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CLOSEOUTS . Once the uniform of the preppy class, madras goes mainstream in Gramicciand#39;s Jalama Paya Madras shirt, an expressively colored plaid in soft, garment-washed cotton with... Gramicci Jalama Paya Madras Shirt - Short Sleeve (For Men) ? LIGHT TURQUOISE

Gramicci Jalama Paya Madras Shirt -...

Sierra Trading Post
$58.00 $39.95

31%

Off

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The Cotton Gingham Woven Shortall features our signature embroidered pony and has a bright, preppy look. Button-down collar. Applied buttoned placket. Short sleeves with sewn cuffs. Ring... Layette Cotton Gingham Woven Shortall

Layette Cotton Gingham Woven Shortall

Ralph Lauren
Ralph Lauren
$35.00 $22.99

34%

Off

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Classic flat-front shorts prep up his look all season long, while the durable cotton construction holds up to warm-weather playtime. Color(s): bedford orange, brick red, course green,... Ralph Lauren 'Preppy' Cotton Shorts (Toddler Boys)

Ralph Lauren 'Preppy' Cotton Shorts...

Nordstrom
$39.50
Free Shipping

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Ralph Lauren Childrenswear Preppy-style seersucker shorts. Inner adjustable button-tab waist for room-to-grow fit. Side slash pockets; back button-welt pockets. Signature pony embroidery at... Preppy Seersucker Shorts, Blue, Toddler Boys' 2T-3T - Ralph Lauren Childrenswear

Preppy Seersucker Shorts, Blue,...

Neiman Marcus
Ralph Lauren
$49.50

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Lightweight twill. Side slash pockets. Back button-through welt pockets. Signature pony embroidery at back waist. Button/zip fly; belt loops. Cotton. Imported. Preppy Cotton Shorts, Tiller Green, 2T-3T - Ralph Lauren Childrenswear

Preppy Cotton Shorts, Tiller Green,...

Neiman Marcus
Ralph Lauren
$39.50

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He'll stay cool, comfortable and a little bit preppy when the sun is shining in gabardine Bermuda shorts by Lacoste. Color(s): canopy pink, dark yellow, light macaroon brown, rockwood jade... Lacoste Gabardine Bermuda Shorts (Little Boys & Big Boys)

Lacoste Gabardine Bermuda Shorts...

Nordstrom
$65.00
Free Shipping

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With playful blue plaid and pull-on styling, our preppy cotton poplin short is bound to be a favorite all season long. 100% cotton poplin. Front pockets with mock back pockets. Mock fly... Blue Pull-On Plaid Shorts by Gymboree

Blue Pull-On Plaid Shorts by Gymboree

Gymboree
Gymboree
$26.95 $9.79

64%

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Preppy style is in season with our plaid cargo short. Colorful pattern pops on sturdy cotton with cargo pockets to keep him prepared for adventure. 100% cotton poplin. Front and back... Orange Pull-on Plaid Cargo Shorts by Gymboree

Orange Pull-on Plaid Cargo Shorts by...

Gymboree
Gymboree
$26.95 $13.29

51%

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FREE SHIPPING at shopbop.com. Bright faux leather piping traces the V neckline and straps of this loose-knit Joy Cioci tank dress, while a pleated peek-a-boo hem adds a hit of preppy... Joy Cioci Lola Sweater Dress

Joy Cioci Lola Sweater Dress

shopbop.com
$395.00 $118.50

70%

Off

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FREE SHIPPING at shopbop.com. Plaid adds a preppy feel to a sleeveless shift dress. A ruffled hem adds feminine flair to the silhouette. Hidden back zip. Lined. Fabric: Brushed weave. 80%... Elkin Basset Dress

Elkin Basset Dress

shopbop.com
$260.00

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This preppy shortall is crafted in soft cotton and features a bold multi-gingham pattern with signature embroidered pony at the chest. Shirt collar Short sleeves Button-front Patch pocket... Ralph Lauren Infant's Gingham Shortall - Color

Ralph Lauren Infant's Gingham...

Saks Fifth Ave
Ralph Lauren
$35.00 $24.50
Free Shipping

30%

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This preppy set features a classic long-sleeved polo-inspired shirt with adorable seersucker pants and a plaid ribbon belt. Shirt Button-down point collar Short sleeves with sewn cuffs... Ralph Lauren Infant's Two-Piece Shirt & Seersucker Pants Set - Test

Ralph Lauren Infant's Two-Piece Shirt...

Saks Fifth Ave
Ralph Lauren
$55.00 $38.50
Free Shipping

30%

Off

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Plain-front madras shorts, made from cotton, offer a classic preppy look for the warm weather. Machine wash. Imported. Plain-Front Madras Shorts

Plain-Front Madras Shorts

Brooks Brothers
$30.00

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Yes you get all 6  t shirts  for $139 pick  colors in   note  box at checkout Essential short-sleeved V Neck T-shirt, cut  from smooth cotton jersey for preppy comfort. V neckline.;... Ralph Lauren Lot Of 6 V Neck T Shirts Special Deal

Ralph Lauren Lot Of 6 V Neck T Shirts...

Shoppers Corner Outlet
Ralph Lauren
$139.00
Free Shipping

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Essential short-sleeved V Neck T-shirt, cut  from smooth cotton jersey for preppy comfort. Yes You Get  All 6 Shirts V neckline.; Even-sewn cuffs and hem.; Our embroidered pony accents the... Ralph Lauren Stripe V Neck T Shirt 6 Pack

Ralph Lauren Stripe V Neck T Shirt 6...

Leslies Outlets
Ralph Lauren
$139.00
Free Shipping

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The preppy Chino Shorts are back for Summer, with a neat, classic cut livened up with a choice of fun checks, spots and florals for festival-friendly fashion. Johnnie b Girl's Chino Shorts

Johnnie b Girl's Chino Shorts

Boden
$40.00
Free Shipping

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The Chino Shorts are a great preppy classic, back this season in a wide selection of classic hues and cheery Summer brights, as well as a new skull and crossbones print. Try a little roll... Johnnie b Boy's Chino Shorts

Johnnie b Boy's Chino Shorts

Boden
$42.00
Free Shipping

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The Innovation 18 Catfish Swim Short from Hugo Boss is a great choice for quality casual swimwear and clean-cut style. We're a big fan of the preppy plaid and functional assetsside pockets,... Hugo Boss Innovation 18 Catfish Swim Short 50238015 XL Yellow

Hugo Boss Innovation 18 Catfish Swim...

Freshpair.com
Hugo Boss
$84.00 $50.40
Free Shipping

40%

Off

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The Innovation 18 Catfish Swim Short from Hugo Boss is a great choice for quality casual swimwear and clean-cut style. We're a big fan of the preppy plaid and functional assetsside pockets,... Hugo Boss Innovation 18 Catfish Swim Short 50238015 Yellow

Hugo Boss Innovation 18 Catfish Swim...

Freshpair.com
Hugo Boss
$84.00 $50.40
Free Shipping

40%

Off

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Crafted from cotton oxford and designed with a modern straight-leg silhouette, this preppy short is a wear-anywhere essential. Polo Ralph Lauren Straight-Fit Hudson Oxford Short

Polo Ralph Lauren Straight-Fit Hudson...

Bloomingdales.com
Ralph Lauren
$89.50

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Crafted from cotton oxford and designed with a modern straight-leg silhouette, this preppy short is a wear-anywhere essential. Polo Ralph Lauren Straight-Fit Hudson Oxford Short

Polo Ralph Lauren Straight-Fit Hudson...

Bloomingdales.com
Ralph Lauren
$89.50

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The Westport polo shirt is preppy all the way with an oversized crest and tipped collar and cuffs. flat-knit collar and cuffsleft chest crest embroiderytennis tail with taped side... STAFFORD PREP Westport Tipped Polo Shirt, White, Mens

STAFFORD PREP Westport Tipped Polo...

jcpenney
Stafford
$30.00 $11.99

60%

Off

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Our classic-fitting Light Blue/white stripe long-sleeved dress shirt, constructed in crisp two-ply cotton and designed in preppy variegated stripes for a refined look. High medium-spread... Ralph Lauren Long sleeve Classic-Fit Striped Regent Blue

Ralph Lauren Long sleeve Classic-Fit...

Shoppers Corner Outlet
Ralph Lauren
$49.00
Free Shipping

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Under Armour Little Boys' Colorblocked Polo Kids Kids Preppy with a sporty edge. Conquer his what-to-wear woes with classic pieces, including this colorblocked polo from Under Armour. Under Armour Little Boys' Colorblocked Polo

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Under Armour Little Boys' Colorblocked Polo Kids Kids Preppy with a sporty edge. Conquer his what-to-wear woes with classic pieces, including this colorblocked polo from Under Armour. Under Armour Little Boys' Colorblocked Polo

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Thakoon Addition's Plaid Jacquard Sweater is sporty with a preppy charm | Large plaid jacquard knit in ivory, Kelly green, and black | Contrasting blue oxford side paneling | Ribbed trim... Plaid Jacquard Sweater

Plaid Jacquard Sweater

Les Nouvelles
$238.00

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Free overnight shipping on Clothing! He'll be the most dapper baby in the room wearing this Armani Junior set. A detachable bow tie adds charm to this preppy look. Top: Contrast collar and... Armani Junior 3 Piece Gift Set with Bow Tie and Pants Boy's Sets - White And Navy

Armani Junior 3 Piece Gift Set with...

Zappos.com
$180.00
Free Shipping

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Free overnight shipping on Clothing! Complement his style with this preppy set. Shirt: Vertical striped pattern. Short sleeves with contrast cuffs. Armani 1982 chest logo. Button down... Armani Junior 2 Piece Set: Stripe Button Down S/S And Logo Short Boy's Sets - Open Misc

Armani Junior 2 Piece Set: Stripe...

Zappos.com
$265.00
Free Shipping

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