Old Money Outfits For Men: How to Look Timeless (2024)

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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How to Look Old Money

  1. What is Old Money?
  2. How to Dress Old Money?
  3. Best Old Money Outfits for Men
    • Best Old Money Outfits for Spring and Summer
    • Best Old Money Outfits for Fall and Winter
  4. Conclusion

What is Old Money?

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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.

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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.

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The Navy Blazer

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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

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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

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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

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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

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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

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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

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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

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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

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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

Conclusion

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.

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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

Summary

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Article Name

Old Money Outfits For Men: How to Look Timeless

Description

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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Editorial Team

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Midway Gentleman

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Old Money Outfits For Men: How to Look Timeless (15)

Old Money Outfits For Men: How to Look Timeless (2024)

FAQs

Old Money Outfits For Men: How to Look Timeless? ›

Consider tailored trousers, dress shirts, polished shoes and timeless accessories like a classic wristwatch, nice long socks or a silk pocket square. For colder months, opt for cashmere or cable-knit sweaters, solid-coloured overcoats, grandad vests and a pair of quality boots.

How to wear old money style men? ›

Consider tailored trousers, dress shirts, polished shoes and timeless accessories like a classic wristwatch, nice long socks or a silk pocket square. For colder months, opt for cashmere or cable-knit sweaters, solid-coloured overcoats, grandad vests and a pair of quality boots.

What are the rules for the old money aesthetic? ›

The Old Money Aesthetic values understated luxury. Don't Neglect Fit and Tailoring: Avoid wearing ill-fitting clothes, as they can detract from the elegance of your outfit. Don't Choose Overly Trendy Pieces: Stay away from ultra-trendy fashion that clashes with the timeless nature of this aesthetic.

How to look like you are from old money? ›

Old money style values high-quality materials and impeccable craftsmanship. Instead of fast fashion items, those who embrace this style invest in high-quality pieces that are built to last. To accomplish the old money aesthetic, focus on curating a wardrobe and selecting pieces that can be worn for years.

What is timeless fashion men? ›

Timeless fashion pieces for men include: White dress shirt: A crisp white shirt is a versatile staple for formal and casual occasions. Navy blazer: A well-fitted navy blazer adds sophistication to any outfit. Dark jeans: Dark, slim-fit jeans are versatile and can be dressed up or down.

How to look rich but casual men? ›

Instead of always wearing T-shirts, try wearing men's plaid shirts over jeans or khakis. In more formal circ*mstances, wear a jacket over your shirt. Dress up in a dress suit once in a while. Go for the business, business casual or/and preppy look.

What are the colors for old money men? ›

Not only do these materials exude opulence, but they also withstand the test of time. Neutral Tones: The color palette of Old Money style tends towards subdued, featuring timeless neutrals such as navy, charcoal, and camel. These colors evoke a sense of sophistication and offer versatility in styling.

How do old money people actually dress? ›

For old money men, traditional tailored suits, blazers, and dress shirts in neutral or darker hues are essential. Old money women, on the other hand, can opt for elegant dresses, blouses, and tailored trousers in equally classic colours.

How to build an old money wardrobe? ›

Essential items include:
  1. Elegant tailored suits.
  2. Sophisticated blazers.
  3. High-quality dress shirts.
  4. Versatile polo shirts.
  5. Classic dress pants and skirts.
  6. Refined dresses and gowns.
  7. Appropriate footwear, including flats and heels.
Mar 5, 2024

What are the colors for old money fashion? ›

Neutral and muted colours are favoured in old money styling. Think navy blues, beige, grey, white and tan. The idea is to create a timeless and elegant look that doesn't rely on flashy or bold colours.

How to dress like a millionaire man? ›

Rich men wear bespoke – or at the very least, made-to-measure. What sets them apart most visibly, even at a distance, is how well their clothes fit. Mid-range, off-the-rack clothing can and will look high-end if you nail the fit. Many department stores and big-box men's retailers have in-store sewing services.

What is the old money stereotype? ›

"Old money" typically refers to families or individuals who have maintained their wealth over several generations. These families often pride themselves on traditions, lineage, and sometimes even blue-blooded ancestry.

What is considered old money rich? ›

What is “old money”? Old money is a cultural phrase referring to wealth that's been inherited or passed down over generations.

How many shirts should a man own? ›

As a shirt-maker, my answer would be as many as possible!. However, realistically I recommend nine shirts for your wardrobe. This will cover shirts to wear at all occasions and events. The nine shirts combine key styles, fabrics, and colour options that will enable you to create several stylish outfits to wear.

What suit should every man own? ›

Common Questions: What 5 suits should a man own? Everyman should own a black suit, a navy suit, a grey suit, a brown suit and a tan suit with white, powder blue or cream shirts.

How does old money actually dress? ›

One of the key elements of dressing with an old money vibe is prioritizing quality over quantity. This means investing in timeless pieces made from natural fabrics like wool, silk, and cashmere. Stick to classic, neutral colors that never go out of style, and avoid trendy, flashy pieces that will quickly look dated.

Are jeans old money men? ›

While jeans may seem more casual, they can be incorporated into old money style when done thoughtfully. Opt for dark, well-fitted jeans and pair them with classic pieces like blazers, dress shirts, and quality footwear. The key is to strike a balance between casual comfort and refined style.

How to dress like rich guys? ›

How to Dress Like You're a Millionaire
  1. Reach for the basics. ...
  2. Dark denim is always "do." ...
  3. Layer your look with a timeless topper. ...
  4. Slip into status staple shoes. ...
  5. When in doubt, wear neutral tones. ...
  6. Drape yourself in timeless jewels. ...
  7. Logo is a no go when it comes to purses. ...
  8. Sunglasses are always a power move.
May 5, 2023

What are the colors for old money style? ›

The old money aesthetic merges neutral colors with deep, rich hues such as dark brown, burgundy, or dark blue to create a rich color scheme that evokes luxury and sophistication.

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