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? ›

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 to dress old money aesthetically? ›

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.

What are the colors for old money 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.

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 best colors for old money? ›

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 give off old money vibes? ›

While the Old Money Aesthetic leans towards more classic attire, well-fitted, high-quality jeans in darker washes can be part of this look. Pair them with a tailored blazer and elegant shoes to maintain the sophisticated vibe.

How to dress simple but 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.

How to build an old money wardrobe? ›

Investment Dressing and choosing Quality Over Quantity sets the cornerstone for this fashion philosophy. Essential Old Money pieces include Classic White Shirt, Trench Coat, Tailored Suits, Little Black Dress and quality leather footwear.

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.

How do you make a timeless look? ›

Mix old and new. Combining finishes, furniture, and features of different eras and styles can help to create a timeless space. That's because your interior will not dominate a particular period or a design style that may be reminiscent of an old trend.

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 colors scream old money? ›

Mainsail White: A timeless shade of white, exuding elegance and sophistication. Summer Sea Blue: Reflecting tranquil waters, it embodies opulence and relaxation. Sailor Red: A deep, proud red symbolizing maritime traditions and adventure.

What is the old money dress code? ›

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 for men? ›

Can you wear jeans in old money style? 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.

What is the old money clothing style called? ›

Old money aesthetic has also been called quiet luxury, which in my opinion is just one part of what embodies the trend. It's not only about pieces with less brand logos, but it's also about a timeless and expensive style that symbolizes high society. And of course, well, the aesthetic is also old.

Is Brooks Brothers old money? ›

Old Money Brands for Men

Brooks Brothers: Known as America's oldest clothing retailer, Brooks Brothers is famous for their classic suits, sport coats, and button-down shirts.

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