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This fashionable boot is a must have! The Eagle boot from Mike Konos can be part of your rugged outdoor look or your preppy evening look. | Smooth leather upper | Medallion cap toe |... Mike Konos Eagle Boot
Mike Konos Eagle Boot
DSW.com
$129.94
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Ralph Lauren Black Label preppy green mercerized mesh cotton 'Charlie' polo. Soft, mercerized mesh cotton knit - available in Green. 97% Cotton / 3% Elastane. 60 Day Return Policy Ralph Lauren Black Label preppy green mercerized mesh cotton 'Charlie' polo
Ralph Lauren Black Label preppy green...
Bluefly
Ralph Lauren Black Label
$175.00 $140.00
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Combed cotton jersey comprises a preppy short-sleeve shirt with a point collar and a three-button placket. Color(s): green multi. Brand: Polo Ralph Lauren. Style Name: Polo Ralph Lauren... Polo Ralph Lauren Print Jersey Classic Fit Polo
Polo Ralph Lauren Print Jersey...
Nordstrom
Ralph Lauren
$125.00
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Classic-fitting golf short, constructed in preppy seersucker gingham in light cotton and cut for maximum ease of movement. Standard-rise belted waist with zip and button closure. Angled... Ralph Lauren POLO GOLF Links Seersucker Short
Ralph Lauren POLO GOLF Links...
Ralph Lauren
Ralph Lauren
$59.99
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A classic-fitting, sophisticated pant is tailored with a relaxed, straight leg, flat front and classic rise in smooth cotton chino. Standard-rise belted waist with a zip fly and button... Ralph Lauren BIG & TALL Preston Vintage Chino
Ralph Lauren BIG & TALL Preston...
Ralph Lauren
Ralph Lauren
$64.99
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Corduroy contrast trim updates a preppy sneaker fashioned from smooth leather and finished with an iconic croc logo at the side. Color(s): white/ dark blue. Brand: Lacoste. Style Name:... Lacoste 'Telesio' Sneaker
Lacoste 'Telesio' Sneaker
Nordstrom
$105.00
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Polish up your casual look with the preppy Bolingbrook sneakers from Polo by Ralph Lauren.Canvas upper in a casual sneaker styleLace-up front with padded collarOverlay and logo detailsSoft... Polo by Ralph Lauren Bolingbrook Shoes (Khaki) - Men's Shoes
Polo by Ralph Lauren Bolingbrook...
Shoes.com
Ralph Lauren
$59.00 $56.05
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Inspired by the same sporty attitude that has made the collection's polos world-famous, this Lacoste waffle tee blends preppy polish and athletic functionality. Waffle-knitting adds extra... Lacoste Long-Sleeve Waffle Tee, White
Lacoste Long-Sleeve Waffle Tee, White
Neiman Marcus
Lacoste
$88.00
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This Lacoste tee maintains the impeccably preppy polish of the collection's polos, but in a more casual mode. Green crocodile embroidery adds a classic accent. Agave red/white/navy stripes.... Lacoste Striped V-Neck Tee, Agave Red
Lacoste Striped V-Neck Tee, Agave Red
Neiman Marcus
Lacoste
$60.00
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Stay true to your preppy style in the Cantor Low sneakers from Polo by Ralph Lauren.Canvas upper in a casual sneaker style with a round toeLace-up front with metal eyeletsLogo and stitching... Polo by Ralph Lauren Cantor Low Shoes (Khaki) - Men's Shoes
Polo by Ralph Lauren Cantor Low Shoes...
Shoes.com
Ralph Lauren
$59.00
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Florsheim Men's Berkley Black Florsheim Men's Berkley Black
Florsheim Men's Berkley Black
TheShoeMart
Florsheim
$95.00
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Ralph Lauren Black Label preppy green cotton 'Rebel' crewneck t-shirt. Soft, lightweight cotton knit - available in Green. 100% Cotton. 60 Day Return Policy Ralph Lauren Black Label preppy green cotton 'Rebel' crewneck t-shirt
Ralph Lauren Black Label preppy green...
Bluefly
Ralph Lauren Black Label
$175.00 $140.00
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Old Navy Packed with pockets, pulsing with pattern! These cargo shorts are seriously cool in more ways than one, thanks to preppy plaids and soft but sturdy cotton. Button closure and zip... Old Navy Mens Plaid Cargo Shorts 12
Old Navy Mens Plaid Cargo Shorts 12
Old Navy
Old Navy
$29.50 $14.49

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Free Shipping on all orders! These high-top sneaks from Original Penguin are retro-chic and preppy perfect all rolled into one! ; Lace-up front with hook-and-loop closure over instep.... Original Penguin Moby Men's Lace up casual Shoes
Original Penguin Moby Men's Lace up...
6pm.com
Original Penguin
$104.95 $65.99
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Tommy Hilfiger Hat, Flag Baseball Hat Shoes MEN'S This baseball hat from Nautica is a simple accessory to aid in your polished and preppy look. Tommy Hilfiger Hat, Flag Baseball Hat
Tommy Hilfiger Hat, Flag Baseball Hat
macys.com
Tommy Hilfiger
$19.99 $14.99

25%

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An essential classic-fitting short is crafted from vibrant cotton madras for a preppy vintage polish. Polo Ralph Lauren Foxcroft Madras Short
Polo Ralph Lauren Foxcroft Madras...
Bloomingdales.com
Ralph Lauren
$79.50 $55.65

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An essential classic-fitting short is crafted from lightweight linen in a preppy madras pattern for an authentic look. Polo Ralph Lauren Beach Shop Linen Madras Short
Polo Ralph Lauren Beach Shop Linen...
Bloomingdales.com
Ralph Lauren
$89.50
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Free Shipping on all orders! These To Boot New York Evan oxfords make a preppy classic new again! ; High-quality leather upper. Front lace-up closure. Contrast stitching and perforation... To Boot New York Evan Men's Lace up casual Shoes
To Boot New York Evan Men's Lace up...
6pm.com
To Boot New York
$195.00 $87.75
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Perry Ellis Socks, Cotton Modal Argyle Men's APPAREL - Underwear A subtle touch of argyle lends preppy polish to these luxuriously smooth socks from Perry Ellis. Perry Ellis Socks, Cotton Modal Argyle
Perry Ellis Socks, Cotton Modal Argyle
macys.com
Perry Ellis
$9.00
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Perfect for layering, this soft, all-cotton argyle tennis vest offers a classic preppy look. Solid jersey back, contrast tipping at v-neck and rib detailing along armholes and hem. Machine... Cotton Tipped Tennis Argyle Vest
Cotton Tipped Tennis Argyle Vest
Brooks Brothers
$69.50
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Maximize your downtime with the laid-back comfort and style of these plaid cargo shorts. They're made with a soft, double weave of yarn-dyed cotton that's as lightweight as it is durable.... Tommy Bahama Denim Pablo Plaid Cargo Shorts Mens Shorts
Tommy Bahama Denim Pablo Plaid Cargo...
Tommy Bahama
Tommy Bahama
$98.00
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Direct from Cole Haan Handcrafted classic penny loafer in premium construcrtion and innovative materials. Genuine handsewn on the last moccasin constructionConcealed NIKE AIR... Cole Haan Air Monroe Penny
Cole Haan Air Monroe Penny
Cole Haan - Official Store
Cole Haan
$198.00 $149.95
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Our classic penny in suede and nubuck is a no-brainer to channel a modernized preppy vibe. Suede and nubuck upperConcealed NIKE AIR TechnologyFully leather linedFull lightweight EVA... Cole Haan Air Monroe Eva Penny
Cole Haan Air Monroe Eva Penny
Cole Haan - Official Store
Cole Haan
$188.00
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Cut with the slightly shorter length and trim fit that define the University silhouette, our crisp and classic short is designed in artfully faded cotton chino for a timeless preppy look.... RUGBY University Chino Short
RUGBY University Chino Short
Rugby.com
Ralph Lauren
$59.50
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Paired with a classic rugby and cleats or dressed up with a blazer and wingtips, the Wadham chino short exudes the masculine appeal of an athletic short while keeping the timeless luster of... RUGBY Wadham Chino Short
RUGBY Wadham Chino Short
Rugby.com
Ralph Lauren
$69.50
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Free Shipping Both Ways! Update your casual collection with the preppy cool Bolingbook sneaker. Leather upper. Lace-up front. Embroidered signature logo on side. Fabric lining. Cushioned... Polo Ralph Lauren Bolingbrook Men's Lace up casual Shoes - Black
Polo Ralph Lauren Bolingbrook Men's...
Zappos.com
Ralph Lauren
$69.00
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Free Shipping Both Ways! Stay preppy fresh with this classic offering from Polo Ralph Lauren. Canvas upper. Lace-up front. Embroidered signature logo on side. Stitch detailing. Fabric... Polo Ralph Lauren Cantor Low Men's Lace up casual Shoes - Blue
Polo Ralph Lauren Cantor Low Men's...
Zappos.com
Ralph Lauren
$59.00
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Campus Suede Men's Casual Shoes. A classic adidas original with a preppy suede upper to give it that frat boy look. Still keeping the 3 solid adidas stripes and rubber sole. Crimson Red ADIDAS Campus Suede Men's Casual Shoes, Crimson Red
ADIDAS Campus Suede Men's Casual...
Finish Line
$64.99 $34.98

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Preppy fashion knows no bounds in Penguin's hands. Classic polo fits, button-front shirts, and blazers show off the liveliest incarnations of plaid and check.100% cotton. 20"" at the knee... Penguin Whitfield Short in Cornstalk
Penguin Whitfield Short in Cornstalk
RevolveClothing.com
$65.00
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Preppy fashion knows no bounds in Penguin's hands. Classic polo fits, button-front shirts, and blazers show off the liveliest incarnations of plaid and check.70% cotton 30% linen. 18"" at... Penguin Plaid Short in Aquamarine
Penguin Plaid Short in Aquamarine
RevolveClothing.com
$79.00
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Banana Republic Pointed collar, clean front, buttoned cuffs. Our Soft Wash shirts undergo a delicate wash cycle for 60 minutes followed by an enzyme wash, giving the shirt a softer and more... Banana Republic Soft Wash Preppy Tartan Shirt
Banana Republic Soft Wash Preppy...
Banana Republic
Banana Republic
$64.50
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Stay on top of things with the Southpole Preppy Shoulder Trim T-Shirt. This 100% cotton t-shirt has screenprinted graphics with felt appliques. Imported. Southpole Preppy T-Shirt With Shoulder Trim - Mens - Black
Southpole Preppy T-Shirt With...
Foot Locker
Southpole
$29.99 $9.99

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The Southpole Preppy Screen And Flock Print Tee doesn't skimp on details. Made of 100% cotton, this fresh t-shirt includes screenprint and raised flock print. Imported. Southpole Preppy Screen&Flock S/S T-Shirt - Mens - White
Southpole Preppy Screen&Flock S/S...
Foot Locker
Southpole
$29.99 $14.99

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Old Navy For that diamond in the rough style, its all about argyle! The preppy pattern adds something extra to this soft V neck sweater, a no brainer pairing with both denim or dress pants.... Old Navy Mens Argyle V Neck Sweater
Old Navy Mens Argyle V Neck Sweater
Old Navy
Old Navy
$29.50
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The Southpole Preppy Woven Trim Thermal features screenprinted graphics with woven appliques. 60% cotton/40% polyester. Imported. Southpole Preppy Thermal With Woven Trim - Men's ( sz. L, Black )
Southpole Preppy Thermal With Woven...
Amazon Marketplace
Southpole
$8.99
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The Southpole Preppy Woven Trim Thermal features screenprinted graphics with woven appliques. 60% cotton/40% polyester. Imported. Southpole Preppy Thermal With Woven Trim - Men's ( sz. L, White )
Southpole Preppy Thermal With Woven...
Amazon Marketplace
Southpole
$8.99
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Inject preppy-cool style to your causal look with this chic cricket sweater from Polo Ralph Lauren -rnV-neck with multicolor stripe, long sleeves, all-over cable knit, slim fit, ribbed... Cream, Red, and Navy Cricket Pullover
Cream, Red, and Navy Cricket Pullover
StyleBop
$355.00
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Get summer ready in cool plaid cargosDon t let the heat hamper your spirit for fun. Lightweight cargo shorts will be your favorite warm weather wear for the comfort and style they offer... Wrangler Mens Cargo Shorts Plaid Gray/Green/Blue
Wrangler Mens Cargo Shorts Plaid...
Kmart
Wrangler
$27.99 $16.79
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The Kangol Jacquard is a new look for this season. The signature Kangol Player style meets a variety of exciting plaids, stripes, checks and argyles for a bold statement. Customers love... Kangol Jacquard Player
Kangol Jacquard Player
DelMonico Hatter
Kangol
$44.99
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Step up your look in this preppy button-up shirt with touches of colorful specks throughout. Whether you wear it with plaid shorts or dark jeans, your killer sense of style is bound to be... GUESS Long-Sleeve Speckled Shirt
GUESS Long-Sleeve Speckled Shirt
GUESS.com
Guess
$89.00 $23.97

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Differentiating stripes enhance the top of a classic, preppy polo. Color(s): white heather. Brand: Penguin. Style Name: Penguin Stripe Polo. Style Number: 513735. Manufacturer part number... Penguin Stripe Polo
Penguin Stripe Polo
Nordstrom
$79.00
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A staple of preppy style, our Links short with a bright gingham pattern is essential for the golf course. Zip fly with a button closure. Belted waist. Side on-seam pockets. 11" inseam. 100%... Ralph Lauren POLO GOLF Links Gingham Short
Ralph Lauren POLO GOLF Links Gingham...
Ralph Lauren
Ralph Lauren
$59.99
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Old-school wool lends a preppy vibe to a laceless sneaker with hidden elastic insets to secure the fit. Color(s): chocolate, dark grey, oatmeal. Brand: Converse. Style Name: Converse 'Jack... Converse 'Jack Purcell' Wool Slip-On Sneaker (Men)
Converse 'Jack Purcell' Wool Slip-On...
Nordstrom
$79.95 $39.90
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Our preppy oxford short with genuine mother-of-pearl buttons is the perfect addition to the summer wardrobe for the classic gentleman. Zip fly. Belted waist with a genuine mother-of-pearl... POLO RALPH LAUREN Preppy Oxford Short
POLO RALPH LAUREN Preppy Oxford Short
Ralph Lauren
Ralph Lauren
$79.50
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A preppy necessity for the summer, our oxford shorts make a statement of subtlety and style. Zip fly. Belted waist with an elongated button tab at the front. Genuine mother-of-pearl... Ralph Lauren BIG & TALL Preppy Oxford Short
Ralph Lauren BIG & TALL Preppy Oxford...
Ralph Lauren
Ralph Lauren
$85.00
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Flat-front, pastel-hued shorts with a preppy aesthetic are finished with back button-flap pockets. Color(s): blue, course green. Brand: Polo Ralph Lauren. Style Name: Polo Ralph Lauren... Polo Ralph Lauren 'Preppy' Shorts (Big & Tall)
Polo Ralph Lauren 'Preppy' Shorts...
Nordstrom
Ralph Lauren
$85.00
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A flat-front garment-dyed short in a classic comfortable cut makes a bright, preppy statement on the golf course. Standard-rise belted waist. Flat front, zip fly with a button closure.... Ralph Lauren POLO GOLF Flat Front Garment Dyed Short
Ralph Lauren POLO GOLF Flat Front...
Ralph Lauren
Ralph Lauren
$54.99
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Ruggedly faded and frayed for a deconstructed vibe, our short takes a preppy, ultra-soft cotton chino downtown with utility-style cargo pockets and distressing. Belted waist, zip fly with a... Ralph Lauren DENIM & SUPPLY Vintage Chino Cargo Short
Ralph Lauren DENIM & SUPPLY Vintage...
Ralph Lauren
Ralph Lauren
$59.50
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This Lacoste tee maintains the impeccably preppy polish of the collection's polos, but in a more casual mode. Green crocodile embroidery adds a classic accent. Navy/white stripes. V... Lacoste Striped V-Neck Tee, Navy
Lacoste Striped V-Neck Tee, Navy
Neiman Marcus
Lacoste
$60.00
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This Lacoste tee maintains the impeccably preppy polish of the collection's polos, but in a more casual mode. Green crocodile embroidery adds a classic accent. White/silver stripes. V... Lacoste Striped V-Neck Tee, White
Lacoste Striped V-Neck Tee, White
Neiman Marcus
Lacoste
$60.00
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Inspired by the same sporty attitude that has made the collection's polos world-famous, this Lacoste waffle tee blends preppy polish and athletic functionality. Waffle-knitting adds extra... Lacoste Long-Sleeve Waffle Tee, Gray
Lacoste Long-Sleeve Waffle Tee, Gray
Neiman Marcus
Lacoste
$88.00
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Preppy plaid elevates a laid-back sneaker cut for a cool, low profile. Color(s): black. Brand: Ben Sherman. Style Name: Ben Sherman 'Breckon' Sneaker. Style Number: 536068. Manufacturer... Ben Sherman 'Breckon' Sneaker
Ben Sherman 'Breckon' Sneaker
Nordstrom
Ben Sherman
$69.95
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Polish up your casual look with the preppy Bolingbrook sneakers from Polo by Ralph Lauren.Canvas upper in a casual sneaker styleLace-up front with padded collarOverlay and logo detailsSoft... Polo by Ralph Lauren Bolingbrook Shoes (Polo Black) - Men's Shoes
Polo by Ralph Lauren Bolingbrook...
Shoes.com
Ralph Lauren
$59.00
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Vintage-inspired driving cap in dapper striped linen. Designed with a flat, floppy top and sewn-down rigid brim. Adjustable back strap with rectangular-ring slider. Our embroidered pony... POLO RALPH LAUREN Estate Driving Cap
POLO RALPH LAUREN Estate Driving Cap
Ralph Lauren
Ralph Lauren
$39.99
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Leather and canvas comprise the upper of a preppy sneaker finished with a Velcro strap across the vamp. Color(s): dress blue/ meadow. Brand: Penguin. Style Name: Penguin 'Moby' High Top... Penguin 'Moby' High Top Sneaker (Men)
Penguin 'Moby' High Top Sneaker (Men)
Nordstrom
$110.00 $79.90
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