Preppy is more than just a fashion style but a lifestyle depicting the rich history and timeless elegance of a bygone era.
As young gentlemen seeking to embrace this refined style, it’s essential to understand the Preppy style’s origin, the evolution of Preppy fashion, the look’s core elements, and how to style it to your unique personality.
In this comprehensive guide, we’ll introduce you to the fascinating world of Preppy style and give you practical advice on creating a collegiate, old-money look that seamlessly adapts to various occasions and seasonal changes.
Preppy Style History – Ivy League Fashion
The roots of preppy fashion, also known as Ivy League fashion or New England style, can be traced back to the hallowed halls of Ivy League universities in the early 20th century.
At institutions like Harvard, Yale, and Princeton, young men from affluent, influential families began to develop a distinct sartorial style that set them apart from their peers.
This classic American menswear look, characterised by classic silhouettes, high-quality materials, and a focus on understated elegance, quickly became a social status and privilege marker.
As these young men graduated and entered the upper echelons of society, they carried their East Coast chic preppy style with them, cementing its association with wealth, power, and refinement.
Preppy Style Wardrobe Essentials
Building a capsule wardrobe of high-quality, versatile Preppy garments that stand the test of time is crucial to embody the Old Money aesthetic.
Here are the essential Preppy clothes, footwear, and accessories you need to create a classic old-money collegiate look, along with styling tips for different contexts and seasons:
Navy Blazers
A well-tailored navy blazer is the cornerstone of any Old Money wardrobe, especially a Preppy one.
Look for a single-breasted, two-button style crafted from a midweight wool fabric, such as a hopsack or serge.
Opt for classic details like brass buttons and patch pockets, and ensure a perfect fit through the shoulders and waist.
J.Press |
Ralph Lauren |
Here is how to style the blazer to achieve an Old Money look.
Iconic Brands
Ralph Lauren, J.Press, Brooks Brothers
Style Icons
Old Money icons, John F. Kennedy and Paul Newman
Tailored Chinos
Invest in several pairs of impeccably tailored chinos in versatile colours like khaki, stone, and navy.
Choose a slim, straight-leg cut that falls just above the ankle, and look for quality construction details like a reinforced waistband and horn buttons.
Brooks Brothers |
Murray’s |
Iconic Brands
Bills Khakis, Murray’s Nantucket Reds, Brooks Brothers
Style Icons
Cary Grant, Steve McQueen
Oxford Cloth Button-Down Shirts
The Oxford cloth button-down (OCBD) is a preppy staple that combines comfort and refinement.
Seek out shirts made from a soft, durable cotton fabric in classic colours like white and light blue, and opt for a trim, flattering fit through the torso and arms.
Gitman Vintage |
Hamilton |
Iconic Brands
Gitman Vintage, Mercer & Sons, Michael Spencer, Hamilton
Style Icons
Gianni Agnelli, Wes Anderson
Knitwear and Sweaters
When temperatures drop, reach for a cosy William Lockie wool sweater in a timeless style like a crewneck cable-knit.
Choose rich, earthy colours like forest green, burgundy, and oatmeal, and look for a medium-weight fabric that will layer easily over your OCBDs.
William Lockie |
Andover Shop |
Iconic Brands
Andover Shop, William Lockie
Style Icons
Ralph Lauren, Prince Charles
Madras Shirts and Shorts
Embrace the preppy staple of madras, a lightweight cotton fabric with a distinctive plaid pattern.
Opt for Madras button-down shirts and shorts in vibrant, summery colours for a classic warm-weather look.
Brooks Brothers |
J.McLaughlin |
Iconic Brands
Brooks Brothers, J.McLaughlin
Style Icons
Dustin Hoffman (The Graduate), John F. Kennedy Jr.
Tweed Sportcoats
Tweed sports coats are quintessential preppy layering garments for cooler months.
Look for a classic herringbone or houndstooth pattern in earthy tones like brown, green, or grey.
Pair with chinos or corduroy trousers for a timeless, professorial vibe.
Brooks Brothers |
J.Press |
Iconic Brands
Brooks Brothers, J.Press, O’Connell’s
Style Icons
Cary Grant, Humphrey Bogart
Rugby Shirts
The rugby shirt, with its bold stripes and rugged cotton fabric, is a preppy staple that exudes a sporty, youthful energy.
Wear it on its own or layered under a blazer for a more polished look.
Ralph Lauren |
Gant |
Iconic Brands
Columbia Knit, Ralph Lauren, Barbarian, Gant
Style Icons
David Hockney, Mick Jagger
Waxed Cotton Jackets
A waxed cotton jacket, like the iconic Barbour Bedale or Beaufort, is a preppy outerwear essential that combines rugged practicality with timeless style.
Wear it over your blazer or sweater for a classic, outdoorsy look.
Barbour |
Belstaff |
Iconic Brands
Barbour, Belstaff
Style Icons
Steve McQueen, Daniel Craig (James Bond)
Preppy Footwear
Footwear is essential to the Preppy aesthetic, as it anchors your outfit and ties together your overall old-money look.
The following classic preppy shoe styles should form the foundation of your footwear collection.
Penny Loafers
A pair of classic penny loafers is an Old Money Preppy footwear essential.
Invest in a high-quality leather pair from a respected brand like Alden or G.H. Bass Weejuns, and choose a versatile colour like brown or cordovan.
G.H. Bass |
Alden |
Iconic Brands
Alden, G.H. Bass Weejuns
Style Icons
Michael J. Fox (Back to the Future), James Dean
Oxford Dress Shoes
Classic Oxford dress shoes in black or brown leather are a must-have for dressier occasions. Look for a sleek, streamlined silhouette with closed lacing and a polished finish.
Allen Edmonds |
Church’s |
Iconic Brands
Allen Edmonds, Church’s
Style Icons
Cary Grant, Fred Astaire
Suede Bucks Derby
Suede buck shoes, or dirty bucks, are a preppy casual staple.
Opt for a light tan or off-white shade, and wear them with chinos, jeans, or shorts for a laid-back, collegiate vibe.
G.H.Bass |
J.Crew |
Iconic Brands
G.H.Bass, J.Crew
Style Icons
Steve McQueen, James Dean
Boat Shoes
No preppy wardrobe is complete without classic boat shoes.
Opt for a high-quality leather pair from a respected brand like Sperry Top-Sider or Sebago, and wear them with chinos, shorts, or even a lightweight summer suit.
Sperry |
Sebago |
Iconic Brands
Sperry Top-Sider, Sebago
Style Icons
John F. Kennedy, Paul Newman
Canvas Sneakers
Simple, understated canvas sneakers like the classic Converse Chuck Taylor All-Stars or Superga 2750 Cotu Classics are perfect for casual preppy outfits.
Choose a neutral colour like white, navy, or grey, and keep them clean and well-maintained.
Jack Purcell |
Superga |
Iconic Brands
Jack Purcell, Superga
Style Icons
John F. Kennedy, Paul Newman
Preppy Accessories
Accessories are the key to elevating your Old Money Preppy outfits and expressing your personal style within the framework of the aesthetic.
Here are a few essential accessories you must consider:
D-Ring Belts
A classic preppy D-ring belt in leather or ribbon is a versatile accessory that adds a touch of casual refinement to any outfit.
Look for belts in preppy motifs like stripes, embroidered critters, or solid colours.
Smathers & Branson |
Kiel James Patrick |
Iconic Brands: Smathers & Branson, Kiel James Patrick
Style Icons: John F. Kennedy, Gianni Agnelli
Baseball Caps
A well-worn baseball cap in a classic style is a preppy staple for casual outings and bad hair days.
Choose a cap with a small logo or no logo at all, and opt for traditional colours like navy, red, or green.
Ebbets Field Flannels |
Polo Ralph Lauren |
Iconic Brands
Ebbets Field Flannels, Polo Ralph Lauren
Style Icons
John F. Kennedy Jr., Prince William
Rope Bracelets
Colourful, nautical-inspired rope bracelets add a playful, summery touch to preppy outfits. Stack them with your watch or wear them independently for a laid-back, seafaring vibe.
Ralph Lauren |
Miansai |
Iconic Brands
Kiel James Patrick, Miansai, Ralph Lauren
Style Icons
John F. Kennedy Jr., Gianni Agnelli
Timepieces
A classic, understated wristwatch is a must-have accessory for any Old Money Preppy dresser.
Look for a simple, elegant design from traditional American makers like Hamilton and Timex or high-end designer brands like Rolex, Omega, or Cartier, and opt for a leather or NATO strap for a touch of casual sophistication.
Hamilton |
Timex |
Iconic Brands
Hamilton, Timex, Rolex, Omega, Cartier
Style Icons
Paul Newman, Steve McQueen, Grace Kelly
Repp Ties
Invest in high-quality neckties in timeless patterns like repp stripes, polka dots, and paisley.
Choose ties made from luxurious materials like silk or wool, and opt for a width that complements your jacket lapels and body type.
Robert Talbott |
Brooks Brothers |
Iconic Brands
Robert Talbott, Brooks Brothers
Style Icons
Cary Grant, JFK, the Duke of Windsor
Leather Goods
Mark Cross |
Ghurka |
From wallets to briefcases to belts, high-quality leather goods are essential to the Old Money Preppy aesthetic.
Look for items crafted from full-grain leather in rich, warm tones like chestnut and burgundy, and opt for classic, understated designs that will stand the test of time.
Remember that less is often more in Old Money Preppy style when accessorising your outfits.
Choose key pieces that complement your look, focusing on quality and craftsmanship over flashy logos or trendy designs.
Iconic Brands
Mark Cross, Swaine Adeney Brigg, Ghurka
Style Icons
Jackie Kennedy Onassis, James Bond, Ernest Hemingway
Master the Preppy Look with The VOU
Mastering the old-money, preppy-infused aesthetic requires patience, dedication, and a deep appreciation for timeless style.
Approach the style with authenticity and a genuine desire to learn and grow, and you’ll develop a refined presence that will serve you well in any situation.
If you are still unsure where to start, find your path with The VOU’s fashion style analysis and embark on a journey of sartorial discovery.
Style Like a True Gentleman
Before we say goodbye, here’s one of the best-kept secrets in men’s styling circles, a secret that only a few expert image consultants know or are willing to share.
First and foremost, professional styling requires knowing your unique body shape and seasonal colour palette – paramount factors in choosing perfectly fitting clothes in colours that complement your skin, eyes, and hair.
Only then can a stylist engage in styling by occasion, location, season, and time of day, with garments, footwear, and accessories from stylistically relevant heritage fashion brands to depict high confidence and success.
Best part? You can find your body shape, seasonal colour palette, and ideal fashion style in less than 5 minutes by yourself, for free, thanks to our four simple steps:
1. Find Your Body Shape
Different garments flatter different silhouettes, so knowing your body shape is the first step in dressing like a confident man.
To find out your unique body shape, take our free body shape quiz for men.
Once you know your unique body shape, take the second free quiz to discover your unique colour palette.
2. Find Your Unique Colour Palette
Remember, the garments that compose your outfits come in various colours, and you must ensure that each hue complements your natural colour.
To do that, you have to find out your seasonal colour palette, and you can do it by taking our free seasonal colour quiz for men.
3. Find Your Ideal Fashion Style
By now, you should already know your body shape and unique colour palette; the next step is to discover your ideal personal fashion style.
The fastest and simplest way is to take our free fashion style quiz for men; it includes your ideal style, outfit ideas, relevant fashion brands, and much more.
4. Professional Image Consultancy with The VOU
And if you want to style like a professional, by occasion, location, season, and time of the day, you can always ask our expert image consultants and fashion stylists for help.
Our styling services for men are the most comprehensive and detailed on the market, backed up by leading stylists who will guide you step by step in creating looks that communicate affluence, elegance, and endless accomplishments.
Remember, wearing luxury brands isn’t enough; to look stylish, confident, and successful, you must first know your body shape, colour palette, and ideal personal style, and only then style by occasion, location, season, and time of day.
Contact us today to save headaches, time, and money – it’s time to dress like a confident, successful gentleman of exquisite fashion taste –Â the first styling assessment is on us!