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Trending Now: Preppy Looks

  • All Shop by Trend
  • Linen Looks
  • Matching Sets
  • Preppy Looks
  • Streetwear
  • Surf & Skate
134 items
Essential Tech Chino Pants
DKNY

Essential Tech Chino Pants

$24.97Current Price $24.97
(72% off)72% off.
$89.50Comparable value $89.50
(27)
Solid Piquè Slim Fit Polo
Brooks Brothers

Solid Piquè Slim Fit Polo

$34.97Current Price $34.97
(49% off)49% off.
$69.50Comparable value $69.50
(167)
Noah Quarter Zip Sweater
Black Friday Deal
DKNY

Noah Quarter Zip Sweater

$24.97Current Price $24.97
(68% off)68% off.
$79.50Comparable value $79.50
(2)
Paradiso Polo
Top Gift
Tommy Bahama

Paradiso Polo

$49.97Current Price $49.97
(49% off)49% off.
$99.50Comparable value $99.50
(100)
Squiggle Slim Fit Pants
Clear the Rack
7 For All Mankind

Squiggle Slim Fit Pants

$26.24 – $89.97Current Price $26.24 to $89.97
(Extra 25% off select items)Includes extra 25% off select items.
$34.99 – $53.98Previous Price $34.99 to $53.98
$198.00 – $208.00Comparable value $198.00 to $208.00
(21)
Shawl Collar Cable Knit Cardigan
Black Friday Deal
XRAY

Shawl Collar Cable Knit Cardigan

$39.99Current Price $39.99
(54% off)54% off.
$88.00Comparable value $88.00
(45)
Crewneck Knit Sweater
Black Friday Deal
XRAY

Crewneck Knit Sweater

$24.99 – $29.97Current Price $24.99 to $29.97
(Up to 63% off select items)Up to 63% off select items.
$68.00Comparable value $68.00
(83)
Glen Eden Quarter-Zip Pullover Sweatshirt
Rodd & Gunn

Glen Eden Quarter-Zip Pullover Sweatshirt

$59.97Current Price $59.97
(53% off)53% off.
$128.00Comparable value $128.00
(27)
Universal Tech Pants
Black Friday Deal
DKNY SPORTSWEAR

Universal Tech Pants

$29.97Current Price $29.97
(66% off)66% off.
$89.50Comparable value $89.50
(30)
Wool Blend Melton Classic Topper
Cole Haan Signature

Wool Blend Melton Classic Topper

$129.97Current Price $129.97
(60% off)60% off.
$325.00Comparable value $325.00
(68)
Stretch Cotton Oxford Button-Down Shirt
Clear the Rack
14th & Union

Stretch Cotton Oxford Button-Down Shirt

$8.98 – $13.48Current Price $8.98 to $13.48
(Extra 25% off)Includes extra 25% off.
$11.98 – $17.98Previous Price $11.98 to $17.98
$59.50Comparable value $59.50
(28)
Cole Haan Melton Coat
Cole Haan Signature

Cole Haan Melton Coat

$149.97 – $159.97Current Price $149.97 to $159.97
(Up to 53% off)Up to 53% off.
$325.00Comparable value $325.00
(62)
Carlsbad Performance Shorts
TravisMathew

Carlsbad Performance Shorts

$49.97Current Price $49.97
(37% off)37% off.
$79.95Comparable value $79.95
(48)
Dorsey Wool Blend Car Coat
Marc New York

Dorsey Wool Blend Car Coat

$99.97Current Price $99.97
(66% off)66% off.
$295.00Comparable value $295.00
(72)
Waylay Shorts
TravisMathew

Waylay Shorts

$49.97Current Price $49.97
(Up to 44% off)Up to 44% off.
$84.95 – $89.95Comparable value $84.95 to $89.95
(27)
The Slim Fit Jeans
Joe's

The Slim Fit Jeans

$79.97Current Price $79.97
(57% off)57% off.
$189.00Comparable value $189.00
(45)
Wool Blend Plush Car Coat
Cole Haan Signature

Wool Blend Plush Car Coat

$119.97Current Price $119.97
(59% off)59% off.
$295.00Comparable value $295.00
(186)
Quilted Puffer Vest
Cole Haan Signature

Quilted Puffer Vest

$59.97Current Price $59.97
(53% off)53% off.
$129.00Comparable value $129.00
(49)
Powerstretch Slim Leg Pants
Black Friday Deal
DKNY

Powerstretch Slim Leg Pants

$19.97Current Price $19.97
(74% off)74% off.
$79.50Comparable value $79.50
(19)
Yarn Dyed Mesh Polo
New!
Polo Ralph Lauren

Yarn Dyed Mesh Polo

$59.97Current Price $59.97
(52% off)52% off.
$125.00Comparable value $125.00
(2)
Fit 2 Slim Fit Stretch Twill Chinos
rag & bone

Fit 2 Slim Fit Stretch Twill Chinos

$84.97Current Price $84.97
(56% off)56% off.
$195.00Comparable value $195.00
(6)
Quilted Puffer Vest
Perry Ellis

Quilted Puffer Vest

$49.97Current Price $49.97
(49% off)49% off.
$98.00Comparable value $98.00
(38)
Bathurst Polo
Clear the Rack
WESTZEROONE

Bathurst Polo

$17.98Current Price $17.98
(Extra 25% off)Includes extra 25% off.
$23.98Previous Price $23.98
$39.97Previous Price $39.97
(15)
Quilted Lined Flight Bomber Jacket
Dockers®

Quilted Lined Flight Bomber Jacket

$79.97Current Price $79.97
(55% off)55% off.
$180.00Comparable value $180.00
(1)
Long Sleeve Cotton Polo
VELLAPAIS

Long Sleeve Cotton Polo

$36.97Current Price $36.97
(70% off)70% off.
$124.99Comparable value $124.99
(1)
Brit for Men Eau de Toilette
Burberry

Brit for Men Eau de Toilette

$39.97Current Price $39.97
(42% off)42% off.
$69.00Comparable value $69.00
(15)
Suede Bomber Jacket
Cole Haan

Suede Bomber Jacket

$229.97Current Price $229.97
(61% off)61% off.
$598.00Comparable value $598.00
(30)
V-Neck Rib Knit Sweater
XRAY

V-Neck Rib Knit Sweater

$29.97Current Price $29.97
(55% off)55% off.
$68.00Comparable value $68.00
(103)
Shawl Collar Cardigan
Black Friday Deal
XRAY

Shawl Collar Cardigan

$34.99 – $39.97Current Price $34.99 to $39.97
(Up to 48% off select items)Up to 48% off select items.
$68.00Comparable value $68.00
(46)
Only a few left
Wallin Stretch Twill Chino Shorts (Regular & Big)
14th & Union

Wallin Stretch Twill Chino Shorts (Regular & Big)

$24.97Current Price $24.97
(64% off)64% off.
$69.50Comparable value $69.50
(84)
Plush Wool Blend Coat
Cole Haan Signature

Plush Wool Blend Coat

$169.97Current Price $169.97
(51% off)51% off.
$350.00Comparable value $350.00
(35)
Solid Stretch Tech Shirt
DENIM AND FLOWER

Solid Stretch Tech Shirt

$19.97Current Price $19.97
(4)
Cape Cayo V-Neck T-Shirt
Clear the Rack
Tommy Bahama

Cape Cayo V-Neck T-Shirt

$18.74Current Price $18.74
(Extra 25% off)Includes extra 25% off.
$24.99Previous Price $24.99
$79.50Comparable value $79.50
(6)
Snappers Elastic Waist 5.5 Inch Stretch Shorts
Vintage 1946

Snappers Elastic Waist 5.5 Inch Stretch Shorts

$39.97Current Price $39.97
(32% off)32% off.
$59.50Comparable value $59.50
(14)
Ronan Penny Loafer (Men)
NEW YORK AND COMPANY

Ronan Penny Loafer (Men)

$29.97 – $34.97Current Price $29.97 to $34.97
(Up to 60% off)Up to 60% off.
$75.00Comparable value $75.00
(5)
Social Cotton Polo Sweater
DKNY SPORTSWEAR

Social Cotton Polo Sweater

$24.97Current Price $24.97
(72% off)72% off.
$89.50Comparable value $89.50
(3)
Pipe Trim Knit Polo
XRAY

Pipe Trim Knit Polo

$24.97Current Price $24.97
(49% off)49% off.
$49.00Comparable value $49.00
(7)
Monogram Logo Crew Neck T-Shirt
Calvin Klein

Monogram Logo Crew Neck T-Shirt

$19.97Current Price $19.97
(48% off)48% off.
$39.00Comparable value $39.00
(1)
Classic Wool Blend Plush Notched Collar Coat
Cole Haan

Classic Wool Blend Plush Notched Collar Coat

$159.97Current Price $159.97
(59% off)59% off.
$398.00Comparable value $398.00
(56)
Tech Chino Shorts
Clear the Rack
DKNY SPORTSWEAR

Tech Chino Shorts

$10.47 – $19.97Current Price $10.47 to $19.97
(Extra 25% off select items)Includes extra 25% off select items.
$13.96Previous Price $13.96
$69.50Comparable value $69.50
(8)
Stand Collar Bib Wool Blend Coat
Cole Haan Signature

Stand Collar Bib Wool Blend Coat

$154.97Current Price $154.97
(52% off)52% off.
$325.00Comparable value $325.00
(10)
Tonal Paisley Velvet Sportcoat (Short, Regular & Long)
Black Friday Deal
TailorByrd

Tonal Paisley Velvet Sportcoat (Short, Regular & Long)

$89.99 – $119.97Current Price $89.99 to $119.97
(Up to 72% off select items)Up to 72% off select items.
$325.00Comparable value $325.00
(9)
For Men Eau de Toilette Mini
COACH

For Men Eau de Toilette Mini

$12.97Current Price $12.97
(53% off)53% off.
$28.00Comparable value $28.00
(27)
Bomber Jacket
DENIM AND FLOWER

Bomber Jacket

$29.97Current Price $29.97
(4)
Quilted Vintage Twill Vest
Union

Quilted Vintage Twill Vest

$39.97Current Price $39.97
(41% off)41% off.
$68.00Comparable value $68.00
(53)
Powerstretch Flat Front Cargo Pants
DKNY

Powerstretch Flat Front Cargo Pants

$29.97Current Price $29.97
(66% off)66% off.
$89.50Comparable value $89.50
(7)
Nylon Bomber Jacket
DENIM AND FLOWER

Nylon Bomber Jacket

$29.97Current Price $29.97
Breezeway Spectator Polo
Tommy Bahama

Breezeway Spectator Polo

$49.97 – $49.99Current Price $49.97 to $49.99
(49% off)49% off.
$99.50Comparable value $99.50
(148)
Solid Cotton Corduroy Sportcoat
TailorByrd

Solid Cotton Corduroy Sportcoat

$59.97Current Price $59.97
(81% off)81% off.
$325.00Comparable value $325.00
(9)
Essential Polo
DKNY SPORTSWEAR

Essential Polo

$19.97Current Price $19.97
(71% off)71% off.
$69.50Comparable value $69.50
(1)
Textured Crewneck T-Shirt
DENIM AND FLOWER

Textured Crewneck T-Shirt

$14.97Current Price $14.97
Only a few left
Luxe Slim Fit Solid Dress Shirt
Perry Ellis

Luxe Slim Fit Solid Dress Shirt

$34.97Current Price $34.97
(49% off)49% off.
$69.50Comparable value $69.50
(28)
Farley Sweater Polo
DKNY

Farley Sweater Polo

$24.97Current Price $24.97
(74% off)74% off.
$98.50Comparable value $98.50
(4)
Johnny Collar Sweater Polo
Black Friday Deal
DKNY SPORTSWEAR

Johnny Collar Sweater Polo

$24.97Current Price $24.97
(72% off)72% off.
$89.50Comparable value $89.50
(3)
The Active Series Solid Gab Tailored Fit Blazer
HAGGAR

The Active Series Solid Gab Tailored Fit Blazer

$109.97Current Price $109.97
(37% off)37% off.
$175.00Comparable value $175.00
(6)
Tremont Quarter Zip Polo
DKNY SPORTSWEAR

Tremont Quarter Zip Polo

$19.97Current Price $19.97
(74% off)74% off.
$79.50Comparable value $79.50
(3)
Torreno Long Sleeve Polo
VELLAPAIS

Torreno Long Sleeve Polo

$54.97Current Price $54.97
(56% off)56% off.
$124.99Comparable value $124.99
(1)
Polo Black Eau de Toilette
Ralph Lauren

Polo Black Eau de Toilette

$42.97Current Price $42.97
(25% off)25% off.
$58.00Comparable value $58.00
(4)
Relaxed Fit Stripe T-Shirt
DENIM AND FLOWER

Relaxed Fit Stripe T-Shirt

$14.97Current Price $14.97
Trim Fit Stripe Cotton Dress Shirt (Regular & Big)
Black Friday Deal
Lorenzo Uomo

Trim Fit Stripe Cotton Dress Shirt (Regular & Big)

$34.99Current Price $34.99
(72% off)72% off.
$125.00Comparable value $125.00
(6)
Water Resistant Soft Shell Jacket
Dockers®

Water Resistant Soft Shell Jacket

$69.97Current Price $69.97
(61% off)61% off.
$180.00Comparable value $180.00
(2)
Soul Fancy Plaid Suit (Regular & Big)
SOUL OF LONDON

Soul Fancy Plaid Suit (Regular & Big)

$139.97Current Price $139.97
(67% off)67% off.
$428.00Comparable value $428.00
(2)
Rennell Wool Blend Coat
Andrew Marc

Rennell Wool Blend Coat

$129.97Current Price $129.97
(58% off)58% off.
$310.00Comparable value $310.00
(9)
Multi Plaid Cotton Sportcoat
TailorByrd

Multi Plaid Cotton Sportcoat

$59.97Current Price $59.97
(81% off)81% off.
$325.00Comparable value $325.00
(11)
Hamilton Leather Loafer (Men)
WINTHROP

Hamilton Leather Loafer (Men)

$59.97Current Price $59.97
(60% off)60% off.
$150.00Comparable value $150.00
(1)
Charter Side Buckle Driver (Men)
ASTON MARC

Charter Side Buckle Driver (Men)

$34.97Current Price $34.97
(50% off)50% off.
$70.00Comparable value $70.00
(5)
Super Stretch Cotton Blend Blazer
T.R. PREMIUM

Super Stretch Cotton Blend Blazer

$89.97Current Price $89.97
(63% off)63% off.
$249.00Comparable value $249.00
(5)
Cotton Grid Knit Camp Shirt
Clear the Rack
DKNY SPORTSWEAR

Cotton Grid Knit Camp Shirt

$10.11 – $29.97Current Price $10.11 to $29.97
(Extra 25% off select items)Includes extra 25% off select items.
$13.48Previous Price $13.48
$98.50Comparable value $98.50
(2)
Cobham Relaxed Fit Jeans
Rodd & Gunn

Cobham Relaxed Fit Jeans

$69.97Current Price $69.97
(45% off)45% off.
$128.00Comparable value $128.00
(12)
Tech Cargo Chino Pants
DKNY

Tech Cargo Chino Pants

$24.97Current Price $24.97
(68% off)68% off.
$79.50Comparable value $79.50
(6)
Trim Fit Long Sleeve Polo
Lorenzo Uomo

Trim Fit Long Sleeve Polo

$39.97Current Price $39.97
(1)
Only a few left
Repeat Tape Layer Logo Graphic T-Shirt
Calvin Klein

Repeat Tape Layer Logo Graphic T-Shirt

$19.97Current Price $19.97
(48% off)48% off.
$39.00Comparable value $39.00
(5)
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