Dress Old Money Style with 17 Must-Have Fashion Essentials
The ‘Old Money’ style is a way of dressing that reflects the look of affluent American and European families who have sustained wealth and wore similar fashion styles over multiple generations.
Also known as ‘Quiet Luxury’ or ‘Stealth Wealth,’ the Old Money style is synonymous with the Preppy style and conveys heritage, long-standing social status, and a commitment to enduring quality over fleeting fashion trends.
Old Money’s way of dressing depicts Preppy aesthetics such as houndstooth, argyle, pinstripes, and colors like navy blue, forest green, and burgundy.
To successfully pull off the Old Money look, you must know the style’s main clothing, footwear, and accessories, how to style and combine, and the leading clothing brands from where you can shop.
1. Royal Navy Blazers
Three-button single or double-breasted blazers with aesthetic roots in British naval attire are the foundation of any Old Money style.
Best for: corporate meetings, business events
Recommended Brands: Brooks Brothers, Ralph Lauren, Loro Piana
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2. Oxford Shirts
Oxford cloth shorts with button-down collars are an American adaptation of traditional British polo shirts in thick cotton.
Best for: office settings, business-casual dinners, and under a blazer at academic events
Recommended Brands: Gant, Tommy Hilfiger, Ralph Lauren
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3. Stripy Polo Shirts
With roots in polo – a game associated with wealthy families, high-quality cotton piqué polo shirts with navy, forest green, or burgundy stripes are critical in creating an Old Money look.
Best for: golf matches, yacht club gatherings, casual brunch
Recommended Brands: Lacoste, Fred Perry, Ralph Lauren
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4. Tapered Chinos
Originating from military uniforms and made from durable cotton twill, tapered chinos in earth tones like khaki or olive green are the ideal bottom-wear choice in the Old Money style.
Best for: business-casual events, art gallery openings, casual dinners
Recommended Brands: J.Crew, Dockers
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5. Aran Sweaters
Knitted from wool and recognizable by their intricate cable patterns, Aran sweaters originate from the Aran Islands off the coast of Ireland.
Best for: skiing trips, hiking expeditions, New Year’s Eve celebrations
Recommended Brands: Inis Meáin, Ralph Lauren
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6. Cricket Pullovers
Cricket pullovers are a direct adaptation of the traditional cricket uniforms – another sport played by Preppies and wealthy Ivy League students – hence its association with the Old Money look.
Best for: attending cricket matches, garden parties
Recommended Brands: Gant, Ralph Lauren
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7. V-neck Cardigans
Very common in academic settings and formal dinners, V-neck cardigans are versatile layering garments in most Old Money outfits.
Best for: Academic lectures, formal dinners, art gallery openings
Recommended Brands: J.Crew, Burberry, Loro Piana
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8. Penny Loafers
Crafted from premium leather or suede, penny loafers epitomize the Old Money ethos of understated luxury and timeless appeal suitable for anything, from business-casual to academic events and weekend brunches.
Best for: Business-casual events, academic symposiums, brunch meetings
Recommended Brands: Bass Weejuns, Gucci, Tod’s
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9. Brogues
Recognizable for their intricate perforations, brogue shoes are a testament to British heritage and artisanal craftsmanship and are ideal for formal events where a polished Old Money appearance is paramount.
Best for: Formal dinners, weddings, and corporate galas
Recommended Brands: Church’s, Crockett & Jones
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10. Sperry Top-Sider Boat Shoes
Initially designed for better traction on boat decks, Sperry Top-Sider shoes have become a signature element in Old Money style.
Best for: Yachting, beachside events, casual summer parties
Recommended Brands: Sperry, Sebago
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11. Wingtip Boots
Characterized by a pointed-toe cap that extends along the sides of the boots, the Wingtip boots are a traditional footwear choice in the Old Money style.
Best for: Formal winter events, upscale dinner parties, art gallery openings
Recommended Brands: Allen Edmonds, Church’s, Grenson
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12. Leather Belts
High-quality brown or black thin leather belts are a must-have accessory to complete the Old Money look.
Best for: paired with chinos or dress trousers for formal and semi-formal events
Recommended Brands: Hermès, Gucci, Salvatore Ferragamo
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13. Silk Ties
Silk ties in traditional patterns like paisley, stripes, and argyle shapes to add a touch of Preppy sophistication.
Best for: Business meetings, formal dinners, and weddings
Recommended Brands: Charvet, Turnbull & Asser, Brooks Brothers
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14. Pocket Squares
Pocket squares made of silk or linen are an essential Old Money accessory used to confer Navy blazers or suit jackets with visual details.
Best for: charity events, operas, and upscale dinner parties
Recommended Brands: Tom Ford, Paul Smith, Ralph Lauren
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15. Leather Gloves
High-quality lightweight leather gloves are vital in conferring the overall Old Money look with an air of exclusivity and refinement.
Best for: winter events, horse races, golfing events
Recommended Brands: Dents, Hestra, Fratelli Orsini
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16. Gold (or Silver) Cufflinks
Cufflinks are significant accessories in the Old Money style and often feature monograms or family crests.
Best for: black-tie events, formal dinners, and crucial business meetings
Recommended Brands: Tiffany & Co., Cartier, Dunhill
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17. Classic Watches
Classic-style wristwatches with straps of rare leather are the finishing touch for the Old Money style.
Best for: Everyday wear, business meetings, and formal events
Recommended Brands: Patek Philippe, Rolex
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What is Considered Old Money?
While the term ‘Old Money’ is contemporary, the fashion style has roots in the early 20th century, specifically in the elite families of the United States, UK, and Europe.
Involved in industries that have been the backbone of their wealth for generations, these families have a long history of attending prestigious educational institutions such as European boarding schools and Ivy League colleges.
The old money style has roots in the traditional dress codes of these institutions and the leisure activities these families engage in, such as sailing, polo, and golf, hence the emphasis on navy blazers with brass buttons, penny loafers, chinos, and cable-knit sweaters.
While Old Money clothing brands have made the style available to the general public, the look is still associated with generational wealth, social status, conservatism, and traditional values.
Old Money Similar Fashion Styles
Preppy | Ivy League | Yuppie | Sloane Ranger | Southern preppy | Northern Preppy
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