The Old Money Preppy aesthetic 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 preppy fashion’s origins, 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 fashion 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, characterized 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 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 Preppy wardrobe.
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.
Iconic Brands
Brooks Brothers, J.Press
Style Icons
John F. Kennedy, Paul Newman
Tailored Chinos
Invest in several pairs of impeccably tailored chinos in versatile colors 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 colors 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 cozy Shetland wool sweater in a timeless style like a crewneck or cable-knit.
Choose rich, earthy colors 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 colors 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 gray.
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 color 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 color like white, navy, or gray, 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 colors.
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 colors like navy, red, or green.
Iconic Brands
Ebbets Field Flannels, Polo Ralph Lauren
Style Icons
John F. Kennedy Jr., Prince William
Rope Bracelets
Colorful, 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
Timepieces
A classic, understated wristwatch is a must-have accessory for any Old Money Preppy dresser.
Look for a simple, elegant design from a respected brand 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
Neckties
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 accessorizing 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.
