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84 Preppy Menswear Styles

From Preppy Hipster Lookbooks to Simplistic School-Boy Runways

— June 5, 2013 — Fashion
Private school attire and collegiate clothing have been making waves through mens fashion for a while now, and these preppy menswear styles are some great examples of how that schoolboy-type look continues to gain popularity in modern day society.

The preppy look encompasses a variety of different clothing options that often includes collared shirts, tucked in ensembles, tightly fitted pants and elegantly designed blazers. The concept of dressing preppy is also often associated with a style that is nicely put together and visually sophisticated and elegant. Men who choose to go for this type of fashion style often appreciate the intricate and carefully thought-out manner in which these outfits are put together.

From bold blazer editorials to preppy pretty boy runways, these sleek menswear styles are allowing men to maintain that youthful and tailored look.
6.9
Score
Popularity
Activity
Freshness
81
Structured Crest Jackets
Structured Crest Jackets
The Brooklyn Circus Varsity Blazer Makes for a Modern Fit
<
80
Effortlessly Preppy Menswear
Effortlessly Preppy Menswear
The Harrods Magazine April 2013 Shoot Features Neutral Tones
<
79
Earth-Toned Ensembles
Earth-Toned Ensembles
The Massimo Sforza Autumn/Winter 2012 Collection is One with Nature
<
78
Casual College Prep Garments
Casual College Prep Garments
The Hill-Side Fall/Winter 2012 Lookbook is Shot All Over the World
<
77
Chromatic Prepster Ads
Chromatic Prepster Ads
The Perry Ellis Spring/Summer 2013 Campaign is Color-Accented
<
76
Shipwrecked Sportswear Editorials
Shipwrecked Sportswear Editorials
The Storm GQ Style China Portrait Series is Weather-Proof
<
75
Brazen Preppy Collections
Brazen Preppy Collections
This Fred Perry x Raf Simons Collection is Boldly Refined
<
74
Preppy Turtleneck Collections
Preppy Turtleneck Collections
The Lanvin F/W 2013 Men's Collection is Poshly Bundled Up
<
73
Polished Professional Promotions
Polished Professional Promotions
The J.Crew Fall 2012 Campaign Stars Prominent Industry Insiders
<
72
Preppy Lecturer Fashions
Preppy Lecturer Fashions
The GANT By Michael Bastian Fall 2013 Menswear Collection is Conservative
<
71
Relaxed Prep Shool Runways
Relaxed Prep Shool Runways
The Kolor Spring/Summer 2013 Collection Mixes Retro and Modern Styles
<
70
English Schoolboy Shoots
English Schoolboy Shoots
The Sebastian Brice Popeye Editorial is Effortlessly Sophisticated
<
69
Cheery-Hued Dapperwear
Cheery-Hued Dapperwear
Errikos Andreou for L'Officiel Hommes Germany Spring 2012
<
68
Layered Houndstooth Runways
Layered Houndstooth Runways
The Tommy Hilfiger Fall/Winter 2013 Collection is Elegantly Timeless
<
67
Retro Lounging Editorials
Retro Lounging Editorials
Dan Martensen Photographs for Telegraph Men's Style SS 2011 Issue
<
66
Bold Blazer Editorials
Bold Blazer Editorials
Florian Van Bael Graces the May 2012 GQ Italia Issue
<
65
Bow Tie-Laden Lookbooks
Bow Tie-Laden Lookbooks
The Charles Olive 2012 Holiday Lookbook is Preppy
<
64
Ultra Preppy Legwear
Ultra Preppy Legwear
Brooks Brothers Create Four Different Designs on One Pair of Pants
<
63
Animal-Infused Prepster Menswear
Animal-Infused Prepster Menswear
The Burberry Prorsum F/W Collection Calls to the Wild
<
62
Leisurely Prepster Ads
Leisurely Prepster Ads
The Interview Sarar Spring/Summer 2012 Campaign is Clean Cut
<
61
Futuristic School-Boy Looks
Futuristic School-Boy Looks
Kris Van Assche Fall/Winter 2012 Collection is Preppy and Modern
<
60
Old-School Preppy Ensembles
Old-School Preppy Ensembles
The Ovadia and Sons SS12 Collection Boasts Versatile Sophistication
<
59
Laid-Back Collegiate Fashion
Laid-Back Collegiate Fashion
Summer Campus in Vanity Fair Italia Adds Punch to Preppy Style
<
58
Dapper Color-Blocked Lookbooks
Dapper Color-Blocked Lookbooks
The ASOS S/S 2012 Collection Has Styles for Everyone
<
57
Preppy Plaid Suits
Preppy Plaid Suits
The Tomorrowland Spring 2010 Lookbook Features Fresh Fashions
<
56
Simplistic School-Boy Runways
Simplistic School-Boy Runways
The SISE Spring/Summer 2013 Collection Embraces Modern Minimalism
<
55
Four-Eyed Mantorials
Four-Eyed Mantorials
The Coach 'Take Preppy' Editorial Emits a Brainy Vibe
<
54
Vibrant Preppy Prints
Vibrant Preppy Prints
Caulfield Preparatory Spring 2010 Collection is Colorful Casual Wear
<
53
Preppy Pastel Menswear
Preppy Pastel Menswear
The Cash CA 2010 March Collection Keeps it Light and Breezy
<
52
Legacy Lumberjack Apparel
Legacy Lumberjack Apparel
The Carharrt WIP Heritage 2012 Fall/Winter Collection is a Crossover
<
51
Prim Prepster Catalogues
Prim Prepster Catalogues
The Carven Spring/Summer 2012 Menswear Collection is Sharply Dressed
<
50
Electric-Hued Optics
Electric-Hued Optics
The Kirk Originals 'Beam' Collection is a Whimsical Take On Glasses
<
49
Sharp Refined Menswear
Sharp Refined Menswear
Mateusz Rogenbuk Looks Prim & Polished for PVOMO Menswear
<
48
Preppy Checkered Menswear
Preppy Checkered Menswear
The APC Madras Collection Follows a Specific Pattern
<
47
English Schoolboy Ensembles
English Schoolboy Ensembles
The Mackintosh Philosophy FW11 Offers Crisp and Tailored Fashion
<
46
Teacher's Pet Couture
Teacher's Pet Couture
The Velour 2010 Fall Lookbook is Ahead of the Curve
<
45
Celebrity Menswear Campaigns
Celebrity Menswear Campaigns
The Mr. Porter 'The Look' is Now Featuring Chase Crawford
<
44
Preppy Skater Captures
Preppy Skater Captures
Pharrell Williams Shows Off His Clothing Brand in Cool Trans Magazine
<
43
Preppy Pink-Hued Menswear
Preppy Pink-Hued Menswear
The Antonio Navas Euroman Editorial Features Fresh Colors
<
42
Abstract Academic Lookbooks
Abstract Academic Lookbooks
The Casely-Hayford S/S 2012 Collection is Dapper and Distinguished
<
41
Ivy League Throwbacks
Ivy League Throwbacks
'The Black Ivy' Photo Series is a Tribute to the First All-Black Colleges
<
40
Moody Teen Lookbooks
Moody Teen Lookbooks
The Vainl Archive 2011 Fall/Winter Line Boasts Dismal Faces & Dapper Style
<
39
Posh Plastic Ensembles
Posh Plastic Ensembles
The Marc Jacobs SS12 Campaign Preview Mixes Minimalist & Modern Styles
<
38
Classic Collegiate Catalogues
Classic Collegiate Catalogues
The H&M Updated Classics Editorial Goes Back to School
<
37
Lookbook Magazines
Lookbook Magazines
'East Side Homeboy' Promotes the Beauty & Youth Fall/Winter 2010 Line
<
36
Economical Hipster Catalogs
Economical Hipster Catalogs
The Lacoste Pre-Fall 2013 Lookbook is Comfortably Chic
<
35
Shredded Menswear
Shredded Menswear
The Fantasticsmag 'Affect Versus Effect' Editorial Shot by Irem Harnak
<
34
Asymmetrical Schoolboy Ensembles
Asymmetrical Schoolboy Ensembles
Miharayasuhiro FW 11/12 Line is Lopsided Preppy
<
33
Preppy Boyish Ensembles
Preppy Boyish Ensembles
The Shipley and Halmos 2012 Spring Line Boasts Youthful Sophsitication
<
32
Debonair Dressed Shoots
Debonair Dressed Shoots
The Helio Martins for Esquire Turkey Editorial is Fit for a Gentleman
<
31
Classy Schoolhouse Style
Classy Schoolhouse Style
The Uniform Experiment SS11 Collection is Prim and Proper
<
30
Preppy Skater Menswear
Preppy Skater Menswear
The Stussy 2010 Spring Collection Combines Two Very Different Fashion World
<
29
Prepster Beachwear
Prepster Beachwear
The Maria Gambina Spring/Summer 2012 Collection is Ready for the Sand
<
28
Pastel Pink Menswear
Pastel Pink Menswear
Lagerfeld Spring 2012 Lookbook Offers Preppy & Casual Men's Styles
<
27
Retro Biking Shirts
Retro Biking Shirts
Fred Perry Cycling Blank Canvas Collection is Inspired by 60s Sportswear
<
26
Ruggedly Sophisticated Lookbooks
Ruggedly Sophisticated Lookbooks
The Rhett Bonnett Fall/Winter Shoot is Impeccably Layered
<
25
Preppy Player Photography
Preppy Player Photography
Nicolas Ripoll in the GQ Style 'Time for Tennis' Editorial
<
24
Eccentric Snobby Lookbooks
Eccentric Snobby Lookbooks
The Beausnob S/S 2012 Collection is Refreshingly Preppy
<
23
Dapper Old-School Fashions
Dapper Old-School Fashions
The Paul Smith GQ Japan Shoot Revisits Classic Menswear
<
22
Gingham-Obsessed Runways
Gingham-Obsessed Runways
The Alexis Mabille Spring/​Summer 2013 Collection is Check-Chic
<
21
Preppy Hipster Lookbooks
Preppy Hipster Lookbooks
The Journal Standard 2013 S/S Lookbook Features Disheveled Menswear
<
20
Urban Prepster Collections
Urban Prepster Collections
The J.Crew Menswear Fall 2012 Lookbook is Sharply Dressed
<
19
Polo Shirts & Bow Ties
Polo Shirts & Bow Ties
The J Lindeberg Spring 2011 Collection Mixes Business Casual & Formal
<
18
Preppy Pretty Boy Runways
Preppy Pretty Boy Runways
The Mango Fall/Winter 2012 Collection Modernizes Classic Styles
<
17
Preppy Class-Cutting Lookbooks
Preppy Class-Cutting Lookbooks
The Mishka 2010 Holiday Collection is Put Together
<
16
Interchangable Lookbooks
Interchangable Lookbooks
The McQ Spring/Summer Lookbook Features Multi-Functional Staples
<
15
Vintage Sports Fashion
Vintage Sports Fashion
The Rugby Ralph Lauren Spring 2010 Collection is Stylishly Preppy
<
14
Hipster School Boy Fashion
Hipster School Boy Fashion
The Customellow Spring/Summer 2011 Collection has Old School Style
<
13
Geek-Chic Menswear Looks
Geek-Chic Menswear Looks
The H&M Spring 2012 Lookbook is Preppy with a Hint of Class
<
12
Preppy Summer Menswear
Preppy Summer Menswear
Terron Wood is a Dapper Nerd for Arnaldo Anaya-Lucca in GQ Germany
<
11
Slick Schoolboy Lookbooks
Slick Schoolboy Lookbooks
The Balmain SS12 Campaign is Too Cool for School
<
10
Fruit-Hued Menswear
Fruit-Hued Menswear
The Apropos Spring/Summer Lookbook Features Contemporary Classics
<
9
Colorful Schoolboy Style
Colorful Schoolboy Style
Francisco Lachowski Shows Preppy Styles for TI 2010 Spring Campaign
<
8
Spec-Tacular Menswear Campaigns
Spec-Tacular Menswear Campaigns
The Dolce & Gabbana Summer Precollection is Suited Up
<
7
School Boy Fashion
School Boy Fashion
The Velour Spring 2010 Collection Brings Style to the Classroom
<
6
Vintage Seaside Menswear
Vintage Seaside Menswear
The Ones2Watch 'Aiguadolc' Editorial has a Nautical Aesthetic
<
5
Composed Menswear
Composed Menswear
The Spring 2011 Men's Collection by Surface to Air is Laid-Back Fierce
<
4
Crisp Color-Blocked Campaigns
Crisp Color-Blocked Campaigns
The United Colors of Benetton Spring/Summer Lookbook is Preppy
<
3
Old Money Menswear Shoots
Old Money Menswear Shoots
The Helge Gjerstad & Marcos F Kenton Editorial is Dapper
<
2
Uber-Preppy Fashion
Uber-Preppy Fashion
The Gant Rugger Spring 2010 Collection Adds Hip to the Square
<
1
Dapper Film Fashion
Dapper Film Fashion
The Great Gatsby Style Influences the Latest Brooks Brothers Collection
<