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Old Money Style Guide: What is it and How to Dress

What is Old Money?

The ‘Old Money’ style is a way of dressing that reflects the sartorial choices of affluent American and European families who have sustained wealth and wore similar fashion styles over multiple generations.

In fashion parlance, terms like ‘new money’ and ‘old money’ imply a connection between when the family’s wealth was acquired and the way of dressing.

Their preferred way of dressing depicts Preppy aesthetics such as houndstooth, argyle, pinstripes, and colors like navy blue, forest green, and burgundy.

In simple terms, the Old Money Style is synonymous with various Preppy styles (Ivy League, Northern, Southern) and conveys heritage, long-standing social status, and a commitment to enduring quality over fleeting fashion trends.

The Origin of 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.

Over time, the style has been made available to the general public by preppy clothing brands, but it is still associated with generational wealth, social status, conservatism, and traditional values.




How to Dress Old Money?

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.

Main Clothing in Old Money Style

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

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

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

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

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

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

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




Main Footwear in Old Money Style

1. 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

2. 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

3. 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

4. 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




Essential Old Money Style Accessories

1. 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

2. 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

3. 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

4. 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

5. 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

6. 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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Similar Styles to Old Money

  • Ivy League
  • Southern preppy


This post first appeared on The VOU, please read the originial post: here

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Old Money Style Guide: What is it and How to Dress

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