Old Money Style Man 2023: How to Dress Like The Elite

The Old Money Style Man represents a timeless and classic approach to fashion, combining elements from American preppy trends with modern silhouettes to create a truly sophisticated look. This style is suitable for those who appreciate the elegance and refinement of the past while still remaining modern and relevant in today’s fashion landscape.

Throughout this article, we will explore the origins of this fashionable movement and provide practical tips on how to successfully achieve the Old Money Style Man look.

Whether you’re a seasoned style enthusiast or just starting to explore the world of fashion, this guide will help you effortlessly incorporate the old money vibe into your daily wardrobe and showcase your unique taste and elegance.

Old Money Style Man: How to Dress Like The Elite

Keep it Classy with Light and Neutral Colors

When dressing like an old money gentleman, remember to stick with lighter colors.

Dark colors like black or navy blue are associated with both wealth and professionalism, but they lack versatility and visual appeal.

Light colors, on the other hand, are seen as more casual and versatile. You can easily dress them up or down depending on the occasion.

Additionally, soft colors like creams, whites, and light blues are more visually appealing than darker colors.

These lighter colors are also more conducive to your overall image. When you dress in darker colors, you make yourself look bigger.

Basically, you’re taking up more space than you need to, making you appear more aggressive and threatening than you really are.

With light colors, you appear friendlier and more approachable.

So lighten up your wardrobe and make a good first impression with light and soft colors.

Throw on a Blazer

A blazer is a great item to have in your closet—whether you’re dressing like an old money gentleman or not.

The best thing about blazers is that they can be dressed up or down depending on the occasion.

While a sports jacket is ideal for a more casual setting, a blazer is more appropriate for a more professional setting.

Therefore, it’s important to have at least one formal blazer in your wardrobe.

For the classiest look, try pairing your blazer with a dress shirt and tie. If you’re dressing like an old money gentleman, you can also add a pair of slacks or chinos to the mix.

Again, a blazer is a great investment piece because you can wear it to a variety of different events.

It’s a great way to add visual interest to a more plain outfit. Most importantly, it’s an excellent way to dress up an outfit without being too stuffy.

Polo Shirts

A polo shirt* is a perfect item to wear while dressing like an old money gentleman.

It’s clean and classic, but it also shows off your own personal style.

If you’re wearing a polo shirt with a suit, make sure it’s also in a light color like yellow, white, blue or pink.

Polo shirts are ideal for casual settings because they’re both easy to wear and clean-looking. It’s a great option for both indoor and outdoor settings. You can also find polo shirts in a variety of patterns and colors.

Pair your polo with a nice pair of khaki pants or chinos and you’re set. It’s a great option for dressing casually during the day.

Classy Accessories like Timeless Watches

For the most part, you want to avoid wearing gaudy jewelry while dressing like an old money gentleman.

The exception is a great watch. While necklaces and rings can sometimes interfere with your work and can make you look too showy, watches are a nice classier accessory to add to your outfit.

If you’re wearing a suit, choose a watch that compliments your outfit.

If you’re wearing a business casual outfit, you can wear a more playful watch.

Regardless of what you choose, make sure that it’s appropriate for the occasion. It’s important to note that watches are a great accessory for dressing like an old money gentleman because they can add visual interest to an otherwise simple outfit.

Furthermore, watches aren’t just functional accessories. Traditionally, they’re symbols of power, status, and wealth.

They’re one of the most expensive accessories you can buy, so they show that you’re willing to invest in your appearance.

Button Down Shirts

Button-down shirts is a staple in every man’s wardrobe.

They can be dressed up or down, depending on the occasion.

When wearing a button-down shirt, you want to make sure that the first few buttons are unbuttoned. This is a classic look that you’ll see on many old money gentlemen.

It’s an easy way to add visual interest to your outfit.

Simply tuck in your shirt and it’ll look like you’re wearing a tie, but you don’t have to wear a tie if you don’t want to.

You can wear your button down shirt with a blazer or sweater if you’d like.

Throw a Sweater over Your Shoulders (Typical Tennis Look)

This is one of the most classic ways to dress like an old-money gentleman.

It’s a style that’s been worn by tennis players for centuries.

It’s a great option if you live in a colder climate or if you’re attending an event where the AC is blasting. Simply pull an sweater over your shoulders.

Make sure it’s a neutral color, like cream or grey. It’s an easy way to add visual interest to your outfit without being too flashy.

Don’t Wear Jeans

For starters, jeans are too casual for most work settings. Moreover, they don’t look professional at all. If you need to dress up for a meeting or just want to look old money, you don’t want to wear jeans.

Instead, try wearing suit pants or chinos. These are more formal and appropriate for work.

If you’re dressing like an old money gentleman, you can wear a blazer over the top of your pants to make your outfit stand out. But if you’re dressing for a casual work setting, you can simply wear pants.

Wear Suit Pants

Suits are classic pieces of clothing that is worn by old money gentlemen.

While they can be expensive, they’re worth investing in because they’re timeless pieces that can be worn year after year. Suits come in many different styles, fabrics, and colors.

You’ll want to pick a fabric that’s appropriate for the season so that you don’t end up too hot or too cold.

Suits are a great option for dressing like an old money gentleman because they’re very professional.

They can be worn to almost any work setting or event. Moreover, there are many different variations of suit pants that you can wear with your suit jacket.

What is the Old Money Style?

Old Money Style Man

The “Old Money Style” is a fashion aesthetic that emphasizes classic, timeless, and luxurious elements. Rooted in upper-class social circles, it represents a refined and sophisticated approach to dressing, favoring quality over quantity and styles that withstand the test of time.

The wardrobe staples for men in the Old Money Style usually include items from reputable and classic brands such as Ralph Lauren and Lacoste. Some additional modern brands like Mango and Luca Faloni also capture the essence of luxury old money.

Key garments of the Old Money Style for men consist of:

  • Tailored suits in classic colors and subtle patterns
  • Well-fitted dress shirts
  • Fine leather shoes, such as oxfords and loafers
  • Iconic polo shirts and tasteful pullover sweaters
  • Structured overcoats and blazers

Alongside clothing, accessories play a significant role in the Old Money Style. Men often opt for:

  • Leather or alligator-skin belts
  • Silk ties with elegant designs
  • Classic cufflinks
  • Luxury timepieces
  • Sophisticated eyewear

Historical Background

Old Money refers to people whose families have maintained their wealth for multiple generations. These individuals inherit not only the financial assets but also the accompanying prestigious social standing and exclusive lifestyle.

In America, the concept of Old Money can be traced back to the Gilded Age, a time when wealthy families displayed their fortunes prominently through their homes, clothing, and leisure activities. These families, such as the Vanderbilts, Astors, and Rockefellers, set the standard for what would come to be known as the Old Money style.

The Old Money aesthetic was initially an expression of the upper echelons of society who embodied a refined and classic sense of fashion. At its core, the Old Money look is about understated elegance, prioritizing quality and timeless pieces over fleeting trends.

Men’s fashion from this era drew inspiration from traditional European styles. Boarding schools, universities, and social clubs served as powerful influences in molding this distinctive look. For instance, the prestigious Ivy League universities in the United States played a significant role in shaping the Old Money style, as they were frequented by students from affluent families.

Over time, the Old Money aesthetic evolved and adapted to include more contemporary elements while still retaining its fundamental essence. Brands like Ralph Lauren and Lacoste emerged as iconic sources of this transformative appeal.

In the modern era, the Old Money style remains synonymous with classic tailoring, understated patterns, and a tasteful color palette. From tailored suits to crisp button-down shirts, the contemporary interpretation of Old Money fashion still echoes the refined taste of days gone by.


Old Money Style Man

How to look like old money for guys?

To look like old money for guys, focus on classic and timeless pieces made from high-quality materials, such as tweed, cashmere, and leather. Stick to neutral and muted colors, and invest in preppy staples like blazers, loafers, and polo shirts. Grooming is also important, so maintain a clean and polished appearance.

How do you style like old money?

To style like old money, focus on classic and timeless pieces that exude elegance and refinement, such as blazers, loafers, and cashmere sweaters. Stick to neutral and muted colors, and invest in high-quality materials like tweed and leather. Accessorize with understated and timeless pieces like a simple watch or a silk scarf. 

What does it mean to dress like old money?

To dress like old money means to adopt a classic and timeless style that exudes elegance, refinement, and sophistication. It often includes traditional materials such as tweed, cashmere, and leather, as well as preppy staples like blazers, loafers, and polo shirts. The focus is on quality, craftsmanship, and understated luxury. 

What brand is for old money style?

Brands like Brunello Cucinelli, Hermès, Loro Piana, and Ralph Lauren are known for their elegant designs, emphasis on quality and craftsmanship, and heritage, which make them popular for the “old money” style. 

How can men look expensive?

To look expensive, men can focus on investing in high-quality and well-tailored pieces, such as suits, blazers, and dress shoes. They can also accessorize with classic and timeless pieces, such as a simple watch or a leather belt. Grooming is also important, so maintaining a clean and polished appearance is key.

What makes a man look rich?

Several factors can make a man look rich, including well-tailored and high-quality clothing, classic and timeless designs, and understated and elegant accessories. Grooming is also important, as a clean and polished appearance can exude confidence and sophistication.

What are old money vibes?

Old money vibes are characterized by an understated elegance and refinement that exude sophistication and class. It often includes classic and timeless designs made from high-quality materials, and is associated with preppy staples like blazers, loafers, and polo shirts. The focus is on quality, craftsmanship, and understated luxury. 

How does old money behave?

Old money is often associated with a certain set of behaviors and values, including discretion, refinement, and a focus on tradition and heritage. Old money families tend to value education, culture, and social connections, and often prioritize philanthropy and giving back to their communities. 

How do you know if a guy has money?

Some signs that a guy may have money include expensive clothing or accessories, a high-end car, or frequent travel to luxurious destinations. However, these are not foolproof indicators of wealth.

*Disclosure: We only recommend products we would use ourselves and all opinions expressed here are our own. This post may contain affiliate links that we may earn a small commission at no additional cost to you.

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