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Preppy Style Guide for Gentlemen

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 – A History of 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 Wardrobe – Old Money 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:

The Navy Blazer

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.

Here is how to style the blazer to achieve an Old Money look.

Iconic Brands
Brooks Brothers, J.Press

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.

Iconic Brands
Bills Khakis, Nantucket Reds

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.

Iconic Brands
Gitman Vintage, Mercer & Sons

Style Icons
Gianni Agnelli, Wes Anderson

Knitwear and Sweaters

When temperatures drop, reach for a cosy Shetland wool sweater in a timeless style like a crewneck or 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.

Iconic Brands
Shetland Woollen Co., Drumohr

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.

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.

Iconic Brands
Harris Tweed, J.Press

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.

Iconic Brands
Rowing Blazers, Barbarian

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.

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.

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.

Iconic Brands
Allen Edmonds, Church’s

Style Icons
Cary Grant, Fred Astaire

Suede Bucks

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.

Iconic Brands
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.

Iconic Brands
Sperry Top-Sider, Sebago

Style Icons
John F. Kennedy, Paul Newman

By building a foundation of these timeless pieces, you’ll be well on mastering the Old Money Preppy look.

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.

Iconic Brands
Converse, 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.

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.

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.

Iconic Brands
Kiel James Patrick, Miansai

Style Icons
John F. Kennedy Jr., Gianni Agnelli


A classic, understated wristwatch is a must-have accessory for any Old Money Preppy dresser.

Look for a simple, elegant design from high-end designer brands like Rolex, Omega, or Cartier, and opt for a leather or NATO strap for a touch of casual sophistication.

Iconic Brands
Rolex, Omega, Cartier

Style Icons
Paul Newman, Steve McQueen, Grace Kelly


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.

Iconic Brands
Hermes, Ferragamo, Brooks Brothers

Style Icons
Cary Grant, JFK, the Duke of Windsor

Pocket Squares

A crisp white linen pocket square is a versatile accessory that instantly elevates any Old Money Preppy outfit.

Experiment with different folding techniques to add visual interest to your blazer or sport coat.

Iconic Brands
Charvet, Simonnot Godard, Drake’s

Style Icons
Fred Astaire, Gianni Agnelli, Tom Ford

Leather Goods

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
Louis Vuitton, Swaine Adeney Brigg, Ghurka

Style Icons
Jackie Kennedy Onassis, James Bond, Ernest Hemingway

Mastering the Old Money Preppy Aesthetic

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.

With over twenty years of front-row fashion and styling events, collabs with haute-couture houses, and a PhD in Luxury Fashion, Laurenti is an expert in crafting personalized looks that depict old-money sophistication.

With years of expertise in high-end fashion collabs and a PhD in Sustainable Fashion, Ru specializes in curating eco-luxe wardrobes for the modern gentleman seeking understated refinement.

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