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? ›

To achieve the old money look, prioritise quality over quantity in your wardrobe. Invest in well-tailored suits, classic jackets, and timeless accessories. Embrace a subdued color palette, focus on subtle patterns, and pay attention to grooming.

How to dress in old money style for men? ›

To achieve the old money look, prioritise quality over quantity in your wardrobe. Invest in well-tailored suits, classic jackets, and timeless accessories. Embrace a subdued color palette, focus on subtle patterns, and pay attention to grooming.

How do you dress old money style? ›

The old money aesthetic is sophisticated and timeless. It embraces classic wardrobe staples that stand the test of time, like a well-tailored blazer or a crisp white button-down shirt. Instead of flashy logos or bold patterns, old money style leans towards understated luxury. It's all about the subtle details.

How do you make a timeless outfit? ›

Here, we delve into the art of building a timeless wardrobe and offer tips for sustainable and stylish fashion choices.
  1. Invest in Quality Pieces. ...
  2. Choose Sustainable Fabrics. ...
  3. Mix and Match. ...
  4. Tailoring and Alterations. ...
  5. Consider a Capsule Wardrobe. ...
  6. Transition Thoughtfully Between Seasons. ...
  7. Support Ethical and Local Fashion.
Sep 28, 2023

How to look classy and rich man? ›

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

How to look rich but casual men? ›

Dress smart and for the occasion.

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 style men? ›

To be counted for old money outfits, you must wear well-tailored suits and jackets/tuxedos in classic cuts and fabrics. Always go for neutral color palettes like navy, gray, beige, and olive, as well as traditional patterns such as pinstripes, houndstooth, Glen plaid, etc.

What are the best colors for old money? ›

The 'Old Money' aesthetic typically favors a neutral and earth-tone color palette, including shades of white, black, beige, navy, and brown.

How to give off old money vibes? ›

So here are some tips as to how to achieve this trendy “old money” look.
  1. Wear neutral colours. The 'old money aesthetic' is all about simplicity and neutral colours such as black, white, beige, brown, cream and pastels. ...
  2. Avoid logos. ...
  3. Choose an appropriate bag. ...
  4. Accessorise.
Oct 13, 2022

How to dress casually and look rich? ›

Always wear clean clothes, freshly pressed, with no threads, rips, stains, or fading. Black, white, navy are always elegant colours that can make you look more expensive. Match your outfit with some assorted accessories such as a couple of bracelets and a pair of sunglasses for that extra visual effect.

What makes a look timeless? ›

What is timeless fashion? Timeless fashion is clothing that is not influenced by current trends and will never go out of style. This means that timeless pieces are classic, elegant, and well-made. If you buy a timeless piece, you can wear it for years without looking outdated.

What is a timeless outfit? ›

Timeless style is all about having a flexible wardrobe that speaks to your style goals and owning great basics is essential to this. You need a foundation of fashion pieces that can be easily mixed and matched and will not look run down or out of style in a year.

What is a timeless piece of clothing? ›

This means that they produce items that are designed to outlive the seasonal trends and last a long time. Often, timeless fashion brands produce ethical fashion which aims to reduce their carbon footprint and stay mindful of the use of fossil fuels while simultaneously producing high-quality garments.

What makes a man look wealthy? ›

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.

How should a 70 year old man dress? ›

If you want to ensure you always look appropriate in your clothes as a 60-plus man, consider investing in classic, timeless pieces. Embracing classic men's fashion styles like a crisp oxford shirt, flat-front chinos, and white leather sneakers will make getting dressed easier and give you more confidence.

What does dressing old money mean? ›

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.

How to dress old money in summer? ›

Linen shirts and dresses: In an old money summer wardrobe, linen garments are a must-have. Lightweight and breathable, linen helps you stay cool while looking effortlessly chic. Pair a classic white linen shirt with tailored shorts or a pleated skirt for the perfect summer ensemble.

What does old money mean clothes? ›

"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.

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