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.

Author

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.

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 do you master old money style? ›

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.

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 to dress old money rich? ›

"Old money" clothing style reflects a timeless and understated elegance associated with established wealth. Characterized by classic, high-quality pieces, it often includes well-tailored suits, traditional patterns like houndstooth or pinstripes, and quality fabrics such as tweed or cashmere.

What are old money colors? ›

In the old money style, there are no bright acidic colors. Things are always predominantly classic deep colors: a lot of white, beige, black, brown, maybe present dark green, dark blue, etc. However, dilution of the outfit with gray, beige, or brown shades is welcome.

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 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 makes an outfit timeless? ›

Timeless fashion is all about creating a wardrobe built around seasonal staples that will last you a lifetime. Sticking to versatile pieces, such as dresses, midi skirts, shirts, jeans, and blazers is essential when creating a capsule wardrobe that can be worn again and again.

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.

Can you wear black in old money? ›

Color of tops should be kept somewhat neutral. Black, beige, brown, white and pastels. Sweaters and coats are best kept black because they will go with everything. Wool pea-coats are something worth splurging on.

What is real old money aesthetic? ›

Also known as quiet luxury, an old money aesthetic is timeless and elegant and prioritises well-made, high-quality, understated garments over flashy designer logos and branding. It's embraced by the wealthy, as it helps signal who they are by what they're wearing in a way that only those in the know will understand.

What is the old money aesthetic style? ›

The Old Money Aesthetic places importance on classic, well-tailored clothing, modest yet exquisite accessories, and a commitment to good manners and social grace.

How does old money actually dress? ›

Monochrome. An all-white or all-black outfit can instantly level up your style. The “Old Money” aesthetic is all about this retro-feel so if you do go for prints, let it be ones that reflect the “old-school” style- like stripes, polka dots, and houndstooth.

How to dress in the old money aesthetic? ›

Tailored dress pants and skirts are fundamental for a refined Old Money look. The key is in the tailoring – each piece should be a reflection of your unique style, cut to perfection. Pair them with a well-fitted blouse and a classic blazer for an ensemble that speaks of sophistication and grace.

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

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