preppy clothing (1,983 RESULTS)

Free Shipping on all orders! Never compromise style to achieve comfort, get the best of both worlds when you step into these stellar SKECHERS GoSleek - Preppy loafers! ; Easy slip-on wear.... SKECHERS Performance GoSleek - Preppy Women's Shoes

SKECHERS Performance GoSleek - Preppy...

6pm.com
Skechers
$54.00 $37.99
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Free Shipping Both Ways! Never compromise style to achieve comfort, get the best of both worlds when you step into these stellar SKECHERS GoSleek - Preppy loafers! ; Easy slip-on wear.... SKECHERS Performance GoSleek - Preppy Women's Shoes - Navy/White

SKECHERS Performance GoSleek - Preppy...

Zappos.com
Skechers
$54.00 $43.99
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The Slim Leather Belt Strap offers two ways to round out your course attire. Solid on one side and screen printed on the other, this genuine leather belt strap lets you choose your style. Oakley Reversible Leather Belt Strap Preppy Pink - Male

Oakley Reversible Leather Belt Strap...

Oakley Vault
Oakley
$29.99

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Free Shipping on all orders! These preppy loafers are perfect for weekend wear. Fabric upper. Signature alligator embroidery. Logo tag at heel counter. Slip-on construction. Fabric lining.... Lacoste Marice LCR Men's Slip on Shoes

Lacoste Marice LCR Men's Slip on Shoes

6pm.com
Lacoste
$70.00 $48.99
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Free Shipping Both Ways! These preppy loafers are perfect for weekend wear. Fabric upper. Signature alligator embroidery. Logo tag at heel counter. Slip-on construction. Fabric lining.... Lacoste Marice USN Women's Shoes - White/White

Lacoste Marice USN Women's Shoes -...

Zappos.com
Lacoste
$70.00 $55.99
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Show off your sea legs in these preppy leather boat shoes. From Eastland, this classic pair is as timeless and stylish as they come. They feature an OrthoLite foam footbed and flexible... Eastland Springfield Womens Leather Boat Shoes, Brown

Eastland Springfield Womens Leather...

jcpenney
Eastland
$90.00
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Show off your sea legs in these preppy leather boat shoes. From Eastland, this classic pair is as timeless and stylish as they come. They feature an OrthoLite foam footbed and flexible... Eastland Springfield Womens Leather Boat Shoes, Brown

Eastland Springfield Womens Leather...

jcpenney
Eastland
$90.00
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Tommy Hilfiger Big Girls' Shoe. How Sweet Are These? Our Ballet Flat / Oxford Hybrid Stands Out In Brilliant Color She'll Love To Wear. Then We Punctuated Them With Classic Brogue... Tommy Hilfiger Oxford Ballet Flats

Tommy Hilfiger Oxford Ballet Flats

Tommy Hilfiger
$29.50

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Rocawear 'Hustlers' Polo Men Men's Clothing - Polos Give your classic preppy look a modern update with this graphic striped design by Rocawear. Rocawear 'Hustlers' Polo

Rocawear 'Hustlers' Polo

macys.com
$49.50

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Rocawear 'Hustlers' Polo Men Men's Clothing - Polos Give your classic preppy look a modern update with this graphic striped design by Rocawear. Rocawear 'Hustlers' Polo

Rocawear 'Hustlers' Polo

macys.com
RocaWear
$49.50

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Free Shipping on all orders! From office wear to preppy casual wear, the Boater slip on from LifeStride is a must-have for your wardrobe. Faux patent leather upper in a casual slip-on... LifeStride Boater Women's Slip on Shoes

LifeStride Boater Women's Slip on...

6pm.com
Lifestride
$55.00 $21.99
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Free Shipping on all orders! These preppy loafers are perfect for weekend wear. Fabric upper. Signature alligator embroidery. Logo tag at heel counter. Slip-on construction. Fabric lining.... Lacoste Marice USN Women's Shoes

Lacoste Marice USN Women's Shoes

6pm.com
Lacoste
$70.00 $48.99
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Free Shipping on all orders! Take a page out of the New England stylebook! Look your best this summer with the preppy New Balance Surfside Thong. Canvas upper with seersucker printed liner.... New Balance Surfside Thong Men's Shoes

New Balance Surfside Thong Men's Shoes

6pm.com
New Balance
$27.95 $22.99
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Free Shipping on all orders! These preppy loafers are perfect for weekend wear. Fabric upper. Signature alligator embroidery. Logo tag at heel counter. Slip-on construction. Fabric lining.... Lacoste Marice US Women's Shoes

Lacoste Marice US Women's Shoes

6pm.com
Lacoste
$70.00 $48.99
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Free Shipping Both Ways! Take a page out of the New England stylebook! Look your best this summer with the preppy New Balance Surfside Thong. Canvas upper with seersucker printed liner.... New Balance Surfside Thong Men's Shoes - Navy/White

New Balance Surfside Thong Men's...

Zappos.com
New Balance
$27.95 $25.99
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Free Shipping Both Ways! These preppy loafers are perfect for weekend wear. Fabric upper. Signature alligator embroidery. Logo tag at heel counter. Slip-on construction. Fabric lining.... Lacoste Marice USN Women's Shoes - Dark Blue/Dark Blue

Lacoste Marice USN Women's Shoes -...

Zappos.com
Lacoste
$70.00 $62.99
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Free Shipping Both Ways! Take a page out of the New England stylebook! Look your best this summer with the preppy New Balance Surfside Thong. Canvas upper with seersucker printed liner.... New Balance Surfside Thong Men's Shoes - Navy

New Balance Surfside Thong Men's...

Zappos.com
New Balance
$27.95 $25.99
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Free Shipping Both Ways! These preppy loafers are perfect for weekend wear. Fabric upper. Signature alligator embroidery. Logo tag at heel counter. Slip-on construction. Fabric lining.... Lacoste Marice US Women's Shoes - Grey/Grey

Lacoste Marice US Women's Shoes -...

Zappos.com
Lacoste
$70.00 $55.99
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Free Shipping Both Ways! Bring a chic look to your preppy style with these skimmers from Tommy Hilfiger! ; Plaid textile upper. Easy slip-on wear. Rounded toe. Dual elastic gore side... Tommy Hilfiger Lilete2 Women's Slip on Shoes - Black Multi/Black Multi/Chic Cream

Tommy Hilfiger Lilete2 Women's Slip...

Zappos.com
Tommy Hilfiger
$69.00
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Free Shipping Both Ways! Bring a chic look to your preppy style with these skimmers from Tommy Hilfiger! ; Plaid textile upper. Easy slip-on wear. Rounded toe. Dual elastic gore side... Tommy Hilfiger Lilete2 Women's Slip on Shoes - Storm Multi

Tommy Hilfiger Lilete2 Women's Slip...

Zappos.com
Tommy Hilfiger
$69.00
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Garment dyed for next level color, this neon polo captures your modern preppy attitude perfectly. Vineyard Vines Neon Garment Dye Classic Fit Polo

Vineyard Vines Neon Garment Dye...

Bloomingdales.com
$79.50

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This reversible belt covers the bases: Wear the leather side at work and, after you punch out, flip it over for a stripe preppy look to match your casual jeans. Bally Stripe & Solid Reversible Belt

Bally Stripe & Solid Reversible Belt

Bloomingdales.com
$250.00

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Tommy Hilfiger 35mm Plaid Suspenders Shoes MEN Upgrade preppy attire with a pair of charming plaid suspenders from Tommy Hilfiger. Tommy Hilfiger 35mm Plaid Suspenders

Tommy Hilfiger 35mm Plaid Suspenders

macys.com
Tommy Hilfiger
$45.00 $31.99

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Polo Ralph Lauren Big and Tall Gingham Checked Linen Shorts Men Men's Clothing - Shorts Tailored with a straight-leg silhouette, this lightweight linen short features a preppy checked... Polo Ralph Lauren Big and Tall Gingham Checked Linen Shorts

Polo Ralph Lauren Big and Tall...

macys.com
$98.00 $69.99

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Nautica Performance Deck Polo Men Men's Clothing - Polos Effortless preppy charm makes this polo from Nautica a must-have for any guy's wardrobe. Nautica Performance Deck Polo

Nautica Performance Deck Polo

macys.com
Nautica
$49.50 $39.99

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Nautica Slub Plaid Shirt Men Men's Clothing - Shirts - Casual Button-Down Shirts (Clearance) Elevate your neat, preppy style with this vibrant plaid shirt from Nautica. (Clearance) Nautica Slub Plaid Shirt

Nautica Slub Plaid Shirt

macys.com
Nautica
$59.50 $24.99

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Polo Ralph Lauren Big and Tall Lobster Polo Men Men's Clothing - Polos Crafted from breathable cotton mesh, this preppy relaxed-fitting polo shirt is accented by allover embroidered... Polo Ralph Lauren Big and Tall Lobster Polo

Polo Ralph Lauren Big and Tall...

macys.com
Ralph Lauren
$110.00 $79.99

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Polo Ralph Lauren Big and Tall Lobster Polo Men Men's Clothing - Polos Crafted from breathable cotton mesh, this preppy relaxed-fitting polo shirt is accented by allover embroidered... Polo Ralph Lauren Big and Tall Lobster Polo

Polo Ralph Lauren Big and Tall...

macys.com
Ralph Lauren
$110.00 $79.99

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Tommy Hilfiger William Plaid Shirt Men Men's Clothing - Shirts Punch up your preppy style with this plaid shirt from Tommy Hilfiger. Tommy Hilfiger William Plaid Shirt

Tommy Hilfiger William Plaid Shirt

macys.com
Tommy Hilfiger
$69.50 $41.99

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Tommy Hilfiger Markin Shirt Men Men's Clothing - Shirts Designed with an allover plaid detail, this lightweight shirt from Tommy Hilfiger gives a vibrant boost to your wardrobe of preppy... Tommy Hilfiger Markin Shirt

Tommy Hilfiger Markin Shirt

macys.com
Tommy Hilfiger
$59.50 $33.99

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