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An empire waist silhouette imbues a classically preppy seersucker dress with pretty charm and light-as-air volume. Crossover bodice with slender shoulder straps. Empire waist has a self-tie...

Ralph Lauren GIRLS 7-16 Seersucker...

Ralph Lauren

$44.99

With a smocked bodice, full skirt and coordinated sash, this gorgeous dress is perfect for every girl's special occasions. Puffed, thick straps, straight neckline with smocking at the...

Ralph Lauren GIRLS 2-6X Silk Taffeta...

Ralph Lauren

$319.99

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Preppy pique keeps your little one cool and comfortable on this Florence Eiseman shortalls. Make the red pop by pairing with a tonal polo. Navy. Tonal button detail. Square neckline. Wide...

Florence Eiseman High-Definition...

Neiman Marcus

$80.00 $60.00

25%

Off

Large logo embroidery decorates a preppy, cap-sleeve polo secured by a quartet of classic buttons at the placket. Color(s): fresco blue, pink lips, white. Brand: Ralph Lauren. Style Name:...

Ralph Lauren Polo Shirt (Toddler)

Preppy plaid patterns a lightweight woven shirt styled with a button-down collar and branded with signature equestrian logo embroidery at the chest.Preppy plaid patterns a lightweight woven...

Ralph Lauren Plaid Button Down Shirt...

Free overnight shipping on Clothing! Strike a poise pose in this preppy shirt. Spread collar. Front button closure. Sleeveless. 68% cotton, 28% nylon, 4% spandex. Dry clean only. Imported....

Tibi Cotton Stretch Shirting...

Zappos.com

$198.00 $149.99

Free Shipping

Preppy pique keeps your little one cool and comfortable on this Florence Eiseman shortalls. Make the red pop by pairing with a tonal polo. Navy. Tonal button detail. Square neckline. Wide...

Florence Eiseman High-Definition...

Neiman Marcus

$80.00 $60.00

25%

Off

Osh Kosh Baby Overalls, Baby Boys Overalls Kids Kids Get him prepped! Add a little preppy plaid style to his everyday wear with these overalls from Osh Kosh.

Osh Kosh Baby Overalls, Baby Boys...

macys.com

Osh Kosh B'gosh

$30.00 $17.99

40%

Off

Tommy Hilfiger Kids Shirt, Little Boys Pietro Short Sleeve Polo Kids Kids This sport-inspired polo from Tommy Hilfiger perfects his preppy look for spring.

Tommy Hilfiger Kids Shirt, Little...

macys.com

Tommy Hilfiger

$18.75

BabyLegs Socks - Preppy

BabyLegs Socks

Diapers.com

$12.00

This preppy short from the Official Outfitter of the 2012 United States Olympic Team features a signature Ralph Lauren pony emblem and side-seam stripes.

Ralph Lauren Childrenswear Toddler...

Bloomingdales.com

$39.50

Free overnight shipping on Clothing! Stylishly shorts with just the right amount of preppy appeal. Trouser short sports a mid rise and regular fit. 8 oz. rigid cotton twill fabrication....

!iT Denim Bureau Trouser Short...

Zappos.com

$64.00

Free Shipping

A classic tee rendered in striped cotton jersey for a preppy look.

Ralph Lauren Childrenswear Toddler...

Bloomingdales.com

Ralph Lauren

$22.50

Preppy school style! Brushed cotton twill with button-tab details and built-in poplin shorts. - 100% brushed cotton twill - Invisible side zipper and adjustable waist for all sizes -...

Crazy 8 Uniform Pleated Twill Skort

Crazy 8

$16.95 $12.71

25%

Off

GS-5002-L Size: 12-18 Months Features: -Set contains a baby romper, baby bib, baby hat, and burp cloth.-Material: 100pct Cotton - Heavyweight Fabric - 220GSM.-Stylish design.-Easily...

Preppy Baby Clothes Gift Set in Blue...

Amazon Marketplace

$47.99

GS-5002-M Size: 6-12 Months Features: -Set contains a baby romper, baby bib, baby hat, and burp cloth.-Material: 100pct Cotton - Heavyweight Fabric - 220GSM.-Stylish design.-Easily...

Preppy Baby Clothes Gift Set in Blue...

Amazon Marketplace

$47.99

Preppy plaid meets pretty flowers in this WonderKids toddler girl's plaid dress.

WonderKids Toddler Girl's Plaid...

Kmart

$7.99

Free Shipping

She'll be preppy in plaid with this colorful dress from WonderKids. The colorful plaid design is enhanced with a blue gross grain ribbon at the waist. A matching diaper cover completes this...

WonderKids Infant and Toddler Girl's...

Kmart

$9.99 $6.99

Free Shipping

30%

Off

Free Shipping Both Ways! Lacoste polo shirt - This quintessential preppy polo adds polish to any little one's outfit.

Lacoste Boy's Short Sleeve Classic...

Lacoste - Official Site

$45.00

Free Shipping

Pretty and preppy clothing from Arrow. With picot trim, this girls' polo gets her wardrobe ready for school. Shop our full line of girls' apparel for more style essentials.

Arrow Picot Polo - Girls Plus

Kohl's

$8.00

Our Striped Jersey Polo Shirt is a kid's classic. The soft cotton and modal jersey short sleeve top has big, bold stripes in navy blue and lavender. A white collar and button placket...

Striped Jersey Polo Shirt

Egg Baby by Susan Lazar

$17.00

Our Striped Jersey Polo Shirt is a kid's classic. The soft cotton and modal jersey short sleeve top has big, bold stripes in light grey and army green. A white collar and button placket...

Striped Jersey Polo Shirt

Egg Baby by Susan Lazar

$17.00

Free Shipping Both Ways! Lacoste polo shirt - This quintessential preppy polo adds polish to any little one's outfit.

Lacoste Boy's Short Sleeve Classic...

Lacoste - Official Site

$40.00 $29.99

Free Shipping

25%

Off

Girls cotton jersey sleeveless swing top. smocking details front and back. embroidery details on front.

Hartstrings Girls 2-6X Toddler Jersey...

Amazon.com

$32.00

Free Shipping

Luxe loungewear gets a modern makeover with our newly beloved basic. This cozy layering piece features a slouchy hood at the back of the neck, drawstring ties, topstitched details at the...

Preppy Plaid Maxi Dress 2-6, Ruby,...

Juicy Couture

$108.00 $69.99

35%

Off

Luxe loungewear gets a modern makeover with our newly beloved basic. This cozy layering piece features a slouchy hood at the back of the neck, drawstring ties, topstitched details at the...

Preppy Plaid Maxi Dress 2-6, Ruby,...

Juicy Couture

$108.00 $69.99

35%

Off

From playtime to head-of-the-class style, this three-piece set offers a variety of looks for your little guy. A classic car graphic and world map decorate a soft tee, while the plaid...

GUESS Shirt, Screen Tee and Shorts Set

GUESS.com

$42.50

$5 Flat Fee Shipping! A preppy polo style your little man needs for school or dressy days! Available Sizes: 2T, 3T, 4T, 5T. Made of 100% cotton pique. Pre washed for softness and to reduce...

Boys Sunny Polo Shirt

The Children's Place

$12.50

$5 Flat Fee Shipping! A preppy polo style your little man needs for school or dressy days! Available Sizes: 2T, 3T, 4T, 5T. Made of 100% cotton pique. Pre washed for softness and to reduce...

Boys Pinkish Polo Shirt

The Children's Place

$12.50

Button him up in preppy plaid for all-day style. Match the chambray trim to some comfy jeans and hell be ready to go! Collared shirt features front utility pockets and button tabs on the...

GUESS Kids Boys Cascade Shirt with...

GUESS.com

$39.50

A sailor girl-inspired t-shirt with clean white contrast stripes in a classic-preppy pink or green.

CLONE GRAVEYARD Windy Striped Knit...

Nautica

$14.99

A sailor girl-inspired t-shirt with clean white contrast stripes in classically-preppy pink or green.

Windy Striped Knit Tee (2T-7)

Nautica

$14.99

A polo dress set with matching diaper cover adds preppy style to your little one's wardrobe. short-sleeve polo dress matching diaper cover cotton jersey washable imported Available in...

Carters Rainbow Dress - Girls...

jcpenney

Carter's

$9.00

Preppy and perfect, your little doll dazzles in a striped polo dress just for her. pullover style heart embroidery heart buttons on placket includes matching diaper cover cotton washable...

Carters Striped Polo Dress - Girls...

jcpenney

Carter's

$9.00

Girls cotton jersey sleeveless swing top. smocking details front and back. embroidery details on front.

Hartstrings Girls 2-6X Little Jersey...

Amazon.com

$32.00

Free Shipping

This boy's US Polo Assn. boy's checkered shirt is preppy in all the best ways. Contrasting T-shirt inserts peek through the shirt's hem, sleeves and at the collar for a laid-back vibe that...

US Polo Assn. Boy's Preppy Checkered...

Sears.com

$28.00 $17.99

Free Shipping

36%

Off

supersoft, classic logo graphic with applique and embroidery, self fabric interior neck taping, vintage abercrombie wash, classic fit, imported 60% cotton/40% polyester

Abercrombie Kids Mackenzie

Abercrombie Kids

$19.50 $9.75

50%

Off

Patchwork-inspired design with front and back pockets plus belt loops. - 100% cotton - Zip fly with button closure - Elastic back waist up to size 24m; adjustable waist for sizes 2y-5y -...

Crazy 8 Patchwork Plaid Short

Crazy 8

$16.95 $7.99

53%

Off

100% nylon, preppy windbreaker, full-zipper closure, heritage logo patch at left chest, cozy hood, front pockets, Classic Fit, Imported

Abercrombie Kids Mackenzie

Abercrombie Kids

$59.50

Polished and preppy -- this Dockers boy's polo shirt is the quintessential dress-to-impress look for the little guy.

Dockers Boy's Striped Polo Shirt

Sears.com

$20.00 $10.00

Free Shipping

50%

Off

A bright hue updates this classic polo rendered in breathable cotton mesh and accented with a preppy embroidered Big Pony and twill player's number. Ribbed polo collar and cuffs....

Ralph Lauren GIRLS 7-16 Polo Dress

Ralph Lauren

$44.99

A preppy short-sleeved polo shirt in breathable cotton mesh is accented with "London" embroidery and a "US Olympic Team" embroidered emblem, celebrating Team USA's participation in the 2012...

Ralph Lauren INFANT BOYS Team USA...

Ralph Lauren

$55.00

A comfortable drop-waist dress in a soft cotton blend is finished with ruffles for a preppy look. Ruffled trim at the collar and chest. Drop-waist silhouette with a ruffled hem. 60% cotton,...

Ralph Lauren GIRLS 7-16 Cascade...

Ralph Lauren

$39.99

A charmingly traditional dress in crisp seersucker cotton has a pretty, full skirt with petticoat, sash and smocking details. Gathered empire-waist silhouette and a full skirt with a...

Ralph Lauren GIRLS 2-6X Seersucker...

Ralph Lauren

$44.99

A timeless dress is perfected with a preppy bib front and a striped grosgrain belt. Single button at the neck, concealed three-button placket. Gingham broadcloth bib. Slightly puffed long...

Ralph Lauren GIRLS 7-16 Gingham Bib...

Ralph Lauren

$44.99

A classically preppy dress is rendered in gingham-print silk taffeta for a perfect party ensemble. Straight neckline with slim straps. Six-buttons at the back neck for easy on and off....

Ralph Lauren GIRLS 2-6X Silk Taffeta...

Ralph Lauren

$329.99

Free Shipping

An essential short-sleeved sport shirt is rendered in woven oxford cotton for signature preppy style. Button-down collar, applied placket, barrel cuffs, shirttail hem. Split back yoke with...

Ralph Lauren INFANT BOYS...

Ralph Lauren

$24.99

A preppy short-sleeved polo shirt in breathable cotton mesh is accented with Olympic embroidery, celebrating Team USA's participation in the 2012 Olympics. Ribbed polo collar with contrast...

Ralph Lauren INFANT BOYS Team USA...

Ralph Lauren

$55.00

A signature polo design is transformed into a sporty, casual dress with the addition of a double-tiered ruffle hem. Ribbed polo collar. Five-button placket. Embroidered pony at the left...

Ralph Lauren GIRLS 7-16 Ruffle Polo...

Ralph Lauren

$29.99

A bright hue updates this classic polo rendered in breathable cotton mesh and accented with a preppy embroidered Big Pony and twill player's number. Ribbed polo collar and cuffs....

Ralph Lauren INFANT GIRLS Perfume...

Ralph Lauren

$29.99

A pretty cotton jersey one-piece is designed for a preppy, nautical look with bold stripes and a ruffled neckline. Straight elasticized neckline with ruffled trim. Elasticized waist and...

Ralph Lauren INFANT GIRLS Striped...

Ralph Lauren

$29.50

A preppy cotton madras skirt is smocked along the waist and adorned with front patch pockets for a perfect match with any favorite top. Elasticized smocked waist. Patch pockets with an...

Ralph Lauren GIRLS 2-6X Madras Skirt

Ralph Lauren

$29.99

This adorable cotton mesh polo romper features a pretty belted sash at the waist and a ruffled hem. Designed in a preppy racerback silhouette. Four-button placket, ribbed polo collar and...

Ralph Lauren GIRLS 2-6X Mesh Polo...

Ralph Lauren

$29.99

A pretty pastel patchwork design and ruffled eyelet trim whimsically update the preppy polo dress in breathable cotton mesh. Comfortable A-line silhouette in an allover design of pastel...

Ralph Lauren INFANT GIRLS Patchwork...

Ralph Lauren

$29.99

A preppy cotton chino skirt is complemented by a jeweled belt for a sweet look. Belted waist, zip fly with a hook-and-bar closure. Angled hand pockets, back right welt pocket. Striped belt...

Ralph Lauren GIRLS 2-6X Jeweled...

Ralph Lauren

$29.99

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