How to Dress Old Money: 17 Must-Have Fashion Essentials

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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 Style

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-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

Loro Piana wool blazer Double-Breasted Wool-Blend Blazer

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

Oversized Fit Luxury Oxford Shirt Regular Fit Stretch Cotton Oxford Shirt

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

Made In France Organic Cotton Striped Polo Slim Fit Cable-Knit Polo Shirt

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

Vintage slim-straight corduroy pant Weekend Chinos, Slim Fit

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

Plated Aran Turtle Neck Aran-Knit Wool-Blend Crewneck Sweater

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

Cable-Knit Cotton Cricket Sweater The Spelman Collection Cricket Sweater

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

Cotton-blend cropped V-neck cardigan sweater Check Wool Blend Cardigan




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

Women's Gucci Jordaan Loafer Kate Loafers in Leather

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

Brushed calfskin lace-ups in Black Tan and Ivory Burnished Calf Brogues

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

Women's Koifish Stripe Boat Shoe Jackman Woman Boat Shoes

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

Wingtip Polished Fumè Brogue Chelsea Boot Tabac Wingtip Fran Boots




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

Jumbo Belt Buckle & Reversible Leather Strap Gg Marmont Jumbo Gg Wide Belt

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

Slim Navy And White Blazer Stripe Repp Silk Tie Silk Blod Tri-Color Striped Tie

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

Silk Pocket Square Silk 'Signature Stripe' Pocket Square

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

Women’s Touchscreen Wool-Lined Leather Gloves with Bow Hairsheep 3 BT Piqué Cashmere

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

Acorn Cuff Links Santos De Cartier Cufflinks

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

patek philippe Classic Watch classical rolex watch

 

What is Considered Old Money?

Old Money Style

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.

Old Money Style

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 the “Old Money” designers and 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

PreppyIvy League | Yuppie | Sloane RangerSouthern preppy | Northern Preppy

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After years of managing hundreds of fashion brands from London's office of a global retailer, Mandy has ventured into freelancing. Connected with several fashion retailers and media platforms in the US, Australia, and the UK, Mandy uses her expertise to consult for emerging fashion brands create top-notch content as an editorial strategist for several online publications.

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