Mastering the art of Old Money Preppy style is all about understanding how to combine classic pieces to create cohesive, timeless looks.
By familiarizing yourself with a few key outfit combinations and drawing inspiration from iconic preppy style icons, you’ll be well on your way to embodying the refined, sophisticated essence of the aesthetic.
We’ll showcase six preppy outfit ideas, classic styling tips, and the best products from curated brands embodying the preppy spirit.
1. Classic Preppy Look
The foundation of any Preppy wardrobe is the classic combination of a navy blazer, an Oxford cloth button-down (OCBD) shirt, khaki chinos, and penny loafers.
Invest in a well-fitted navy blazer from a brand like Brooks Brothers or J.Press, known for its quality craftsmanship and attention to detail, to achieve this timeless look.
Pair it with a white or light blue OCBD shirt from Gitman Vintage or Mercer & Sons and khaki chinos from Bills Khakis or Nantucket Reds.
Nantucket Red shorts are iconic to the preppy style because of their unique color: a faded, reddish-pink hue.
The color is achieved through a special dyeing process and is synonymous with preppy fashion’s laid-back, summer-oriented aspect.
Murray’s Toggery Shop is credited with introducing Nantucket Reds and remains a go-to source for this classic preppy staple.
Complete the outfit with brown penny loafers from Alden or G.H. Bass Weejuns, a leather D-ring belt from Smathers & Branson, and a simple, understated wristwatch from Timex or Daniel Wellington.
Style Icons
- John F. Kennedy, the 35th President of the United States, was known for his preppy look, which consisted of navy blazers, white shirts, and khaki chinos.
- Paul Newman, an iconic American actor who exemplified the preppy look on and off-screen, frequently sporting OCBDs, chinos, and loafers.
2. Nautical Prepster Look
Preppy style has strong ties to the nautical world, and this sailor-inspired outfit perfectly captures that spirit.
Start with a pair of Nantucket Red shorts from Murray’s Toggery Shop, the original purveyors of this iconic color.
Pair them with a navy and white striped Breton shirt from Saint James or Armor Lux, two brands with a rich history of producing these classic nautical tops.
For a touch of maritime flair, wear brown top-sider boat shoes from Sperry and a braided rope bracelet from Kiel James Patrick or Miansai.
Top off the look with a nautical logo baseball cap from Vineyard Vines or Southern Tide, classic square Ray-ban sunglasses, and a Bremont diving watch.
Style Icons
- John F. Kennedy Jr., son of President John F. Kennedy, was renowned for his nautical-inspired outfits, including Breton striped shirts and boat shoes.
- Humphrey Bogart is a legendary American actor who popularized the classic nautical-inspired uniform as Captain Queeg in “The Caine Mutiny.”
3. Scholarly Gentleman Look
To channel the academic side of the Preppy aesthetic, start with a tweed sport coat from a heritage brand like Harris Tweed or J.Press.
Choose a classic pattern like herringbone or houndstooth in a muted color like olive green or rust.
Layer it over a button-down shirt from Kamakura Shirts or Proper Cloth in a complementary color, like pale pink or light blue.
Pair this with dark brown corduroy trousers from Orvis or Peter Millar, cuffed at the ankle to reveal a pair of colorful socks from Happy Socks or Pantherella.
Corduroy is a quintessential preppy fabric for its durability, comfort, and texture.
The ridged corduroy texture adds visual interest and depth to an outfit, making it an ideal pairing with tweed’s rustic, nubby texture.
Together, these fabrics create a layered, sophisticated look that embodies the academic and outdoorsy elements of the preppy aesthetic.
Complete the look with suede Oxford shoes from Allen Edmonds, a silk pocket square from Drake’s, a wristwatch with a leather or tweed strap from Seiko, and original Ivy League P3 tortoiseshell glasses from Ben Silver.
Style Icons
- Cary Grant is an iconic British-American actor known for his refined, academic-inspired style, as seen in his role in “Love in the Afternoon.”
- Anthony Perkins is an American actor known for his role as Tom Ripley in “The Talented Mr. Ripley,” in which he showcased a scholarly preppy style with his tweed jackets, Oxford shirts, and tortoiseshell glasses.
4. The Weekender Prep Look
 
For a casual old-money look, start with a pair of well-worn jeans from Gant, rolled up a couple of times for a relaxed vibe.
To maintain the preppy aesthetic, jeans should have a classic, straight-leg style and a dark wash.
Dark wash denim is more polished and refined than lighter washes, making it more suitable for the preppy look.
Straight-leg jeans provide a timeless, balanced silhouette that pairs well with the other classic elements of the preppy wardrobe.
Pair the jeans with a rugby shirt from Drake’s or Rowing Blazers.
These shirts feature bold stripes in classic color combinations, such as navy and white or green and gold.
Layer a cardigan from Ralph Lauren over the rugby shirt for added warmth and texture.
Slip on classic canvas sneakers, like Converse Jack Purcells or Superga 2750 Cotu Classics, and finish the look with a baseball cap from Ebbets Field Flannels or a knit beanie from Polo Ralph Lauren.
Style Icons
- Steve McQueen, an American actor known for his cool, casual style, is photographed in jeans, rugby shirts, and canvas sneakers.
- The British artist David Hockney is recognized for his laid-back, preppy weekend style. He frequently wears relaxed-fit jeans and colorful knitwear.
5. Preppy Sportsman Look
Outdoor pursuits have long been associated with the Preppy lifestyle, and this British Old Money style outfit combination perfectly captures the spirit of the sporting gentleman.
Start with a pair of hunting corduroy pants in a rich, earthy color like forest green or burgundy from a brand like Laksen.
Hunting corduroy pants differ from regular corduroy trousers in their construction and features.
These pants have reinforced knees and seat areas to withstand the wear and tear of outdoor activities.
They may also feature additional pockets or a more rugged construction to accommodate the wearer’s needs during hunting or other outdoor pursuits.
Pair the trousers with a Ralph Lauren tattersall check shirt, which features a classic pattern of thin, intersecting lines in complementary colors, and a cashmere tie from Darke’s.
Layer a merino wool sweater vest from J.Press or Brooks Brothers over the shirt for added warmth and texture.
Complete the look with Wellington boots from Hunter, a waxed cotton jacket from Barbour or Belstaff, and a newsboy cap from Lock & Co. Hatters or Stetson.
Accessories are key to elevating the Preppy sportsman look, such as a pair of leather shooting gloves from Hestra, a silk paisley pocket square from Drake’s, and a classic field watch from Hamilton.
Consider adorning your jacket with a vintage-inspired pin or patch featuring a hunting motif, such as a pheasant or a retriever, for a touch of sporting flair.
Style Icons
- The Duke of Windsor’s impeccable sporting attire comprises tweed jackets, corduroy trousers, and riding boots.
- Ralph Lauren is an American fashion designer whose iconic ads feature models in classic outdoor pursuits, embodying the essence of the preppy sportsman.
6. Tennis Club Prep Look
The preppy aesthetic has strong ties to tennis, and this outfit combination perfectly captures the spirit of the country club set.
Start with a pair of white tennis shorts from a brand like Lacoste or Fred Perry, known for their iconic tennis apparel.
Pair the shorts with a polo shirt in a bold, preppy color like Kelly Green or Royal Blue, featuring the brand’s signature embroidered logo.
Layer a lightweight cotton tennis sweater over the polo for a touch of old-school sophistication.
Characterized by a V-neck, cable knit texture, and contrasting trim, the tennis sweater is a classic preppy garment.
The V-neck makes the polo shirt’s collar visible, while the cable knit texture adds visual interest and a touch of traditional style.
Contrasting trim, such as stripes along the neckline or cuffs, is a common feature that further enhances the sporty, preppy look.
Complete the look with classic white tennis sneakers like the Fred Perry B721 or the Tretorn Nylite and vintage-inspired sunglasses from Persol or Ray-Ban.
Accessories are essential to nailing the tennis club prep look, such as a tennis headband, white wrist sweatbands from Adidas, and a vintage-inspired tennis racket from Wilson.
For a touch of Preppy flair, consider sporting a club tie or a needlepoint belt featuring a tennis motif, such as a racket or a ball.
Style Icons
- Arthur Ashe is a legendary American tennis player known for his stylish on-court presence, which includes polo shirts, tennis shorts, and classic sneakers.
- Bill Tilden, a dominant American tennis player in the 1920s, was photographed in classic tennis attire, including cable-knit sweaters and white trousers.
Master the Preppy Look
By incorporating these specific outfit combinations and product recommendations into your wardrobe, you’ll be able to create a range of preppy looks that are both stylish and authentic.
Remember, the key to mastering the Preppy style is to focus on quality, fit, and attention to detail while drawing inspiration from the icons who have helped shape and define the aesthetic over the years.
Gentlemen, crafting an old-money look is all about paying attention to the finer details, and your choice of dress shoes plays a pivotal role.
Dress Preppy Style Like a Pro
At The VOU, our expert stylists are dedicated to helping you navigate the world of classic footwear, ensuring that you always step out in style.
Whether you’re attending a formal gala, a business meeting, or a relaxed social gathering, we’ll guide you in selecting the perfect pair of dress shoes to complement your ensemble.
From the timeless elegance of Oxfords to the laid-back sophistication of loafers, we’ll help you build a shoe collection that reflects your unique personality and aspirations.
Find your unique style today with The VOU’s fashion style analysis and embark on a journey of sartorial discovery.
Let us be your trusted partner in mastering the art of old money style, empowering you to exude confidence and charm in every setting.
Until next time, keep putting your best foot forward!
