Old Money Outfits For Men: How to Look Timeless

Step into the world of timeless elegance and sophistication as we dive into the captivating realm of Old Money Outfits for Men. Discover the secrets behind crafting a polished and distinguished look that exceeds trends, celebrating the timeless allure of classic style.

Succession' Season 3 Scene

Experience old money’s classic aesthetic and timeless style that bleeds sophistication, discretion, and understated elegance. There’s no shouting logos here, with old money outfits the style, fit and fabric will tell the story, not the logo.

Whether you’re in your twenties, thirties, or forties, you’ll find something new in these outfits. Old money has already stood the test of time and will be just as stylish 10 years from now as it is today.


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What is Old Money?

Princess Diana Old Money Outfit, 1994

To answer it shortly, old money refers to inherited wealth that has been passed down through generations, often associated with established, socially prominent families.

Unlike new money, which is recently acquired, old money implies a longstanding legacy of financial stability and social status.

If this is your first time hearing about old money, I recommend reading our article on the topic: Old Money Aesthetics: What’s the Hype About?

How to Dress Old Money?

Dressing Old Money as a man involves timeless, classic, and understated styles.

Opt for high-quality, tailored clothing in neutral colors with brands known for heritage and craftsmanship. Brands like Ralph Lauren, Loro Piana, or Brioni offer timeless pieces that will last you a lifetime if you care for them.

Choose elegant accessories and avoid flashy logos, reflecting a sense of refined taste and sophistication.

Old Money Outfits for Men: White T-Shirt

Best Old Money Outfits for Men

Best Old Money Outfits for Spring and Summer

The Preppy Polo Look

This outfit presents an array of options, featuring a stylish polo shirt in either white, pastel colors, or classic navy, paired with khaki or gray chinos, or dress pants.

The outfit usually includes a brown leather belt, but for this particular instance, the belt was skipped. The outfit could be completed with a choice of boat shoes, loafers, or even white sneakers.

Old Money Outfits for Men: White Polo Summer Outfit

The Navy Blazer

Old Money Outfits for Men: Navy Blue Blazer

The outfit consists of a navy blazer, a light-colored dress shirt, khaki or gray dress pants, brown leather loafers, and optionally, a patterned silk tie and pocket square.

If you want to dress it up, you can add a tie, but for a more casual look, you can unbutton the top two buttons and skip the tie.

The Classic Oxford Shirt

Old Money Outfits for Men: Oxford Shirt with Gray Pants

Pair a crisp white Oxford shirt with charcoal gray merino wool trousers, add a brown leather belt, and complete with classic wingtip brogues – or, skip the belt, go for side adjustable pants and a patterned necktie.

The Houndstooth Check

Houndstooth Sport Coat Outfit

To achieve this look, pair a houndstooth sport coat or blazer with gray flannel trousers, and complement it with a light blue or plain white dress shirt, and a tasteful striped tie, and complete the outfit with polished leather dress shoes.

For a more relaxed appearance, skip the tie and add a stylish pocket square. This outfit will be perfect for casual and formal events during summer.

The Seersucker Suit

Old Money Outfits for Men: Linen Suit Outfit
Old Money Outfit by Carlos Roberto and Amanda Roya

The outfit exudes a timeless charm with a seersucker suit jacket and matching seersucker suit pants, elegantly combined with a light-colored linen dress shirt.

Optionally, you can add a necktie for a touch of sophistication. For sunny summer days, you can choose to leave the necktie at home. The outfit is completed with a pair of brown leather loafers.

Best Old Money Outfits for Fall and Winter

The Tweed Suit

Old Money Outfits for Men: Tweed Suits

The outfit features a tweed suit jacket paired with tweed suit pants, complemented by a burgundy dress shirt, and completed with a pair of brogues or leather oxfords.

It’s a versatile outfit that can be worn on many formal occasions.

The Camel Hair Overcoat

Old Money Outfits for Men: Camel Hair Coat Men Outfit

The outfit features a camel hair overcoat elegantly matched with a beige turtleneck, light-washed denim jeans, and a pair of Chelsea boots.

It exudes timeless sophistication, capturing the essence of refined taste and ageless fashion. Prepare to make a bold and lasting impression with this look. This outfit is perfect for fall and early winter weather; it also perfectly matches the colors of nature.

The Traditional Tuxedo

Old Money Outfits for Men: Black Tuxedo Outfit

The tuxedo is the king of the modern gentleman’s formal attire.

This look features a black tuxedo jacket with satin lapels paired with matching black tuxedo pants adorned with satin stripes, accompanied by a pleated white tuxedo shirt, a classic black bow tie, and polished off with sleek patent leather shoes.

The Cable Knit Sweater

Old Money Outfits for Men: V-Neck Sweater and Pants

For this outfit, combine a cable-knit cashmere sweater in either a v-neck or crewneck style, paired with light-colored chinos, and completed with a choice of penny loafers or suede driving shoes.

Additionally, you can throw on a pair of shades and your favorite wristwatch.

The Trench Coat

Old Money Outfits for Men: Black Trench Coat Outfit

The perfect outfit for those gloomy autumn days.

The outfit features a black or khaki trench coat layered over a navy blue suit, elegantly paired with a white dress shirt. The look was completed with sleek black leather dress shoes, adding a touch of refinement and sophistication.

For more inspiration, read: The Only Old Money Style Guide You Need This Winter


Remember that these outfits draw inspiration from old-money aesthetics, which feature classic and refined styles. Feel free to mix and match them according to your personal preferences and the occasion you’re attending.

Striving for a classy and timeless look involves working towards achieving the old money aesthetic.

Old Money Outfit Including Light Blue Shirt and White Pants
Old Money Outfit Inspiration

With a versatile wardrobe, you can mix pieces and the results will still look good, only look out for certain rules that we talked about in a previous article: How to Look Old Money on a Budget

Old Money Outfits For Men: How to Look Timeless
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Old Money Outfits For Men: How to Look Timeless
Discover the art of timeless elegance with Old Money outfits for men. Unveil the secrets of classic style and sophistication in our comprehensive guide.
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Midway Gentleman
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