Old Money Style Man 2024: 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 remaining current and relevant in today’s fashion landscape.

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

Key Things to Know:

  • Choose light and neutral colors
  • Invest in a formal blazer
  • Incorporate polo shirts into your wardrobe
  • Go for high-quality fabrics like linen, silk or cotton
  • Wear less jeans and more suit pants
  • Throw away your jeans and sweatpants – they are anything but elegant

Old Money Style Man: How to Dress Like The Elite

Keep it Classy with Light and Neutral Colors

Remember to stick with lighter colors when dressing like an old money gentleman.

Dark colors like black or navy blue are associated with wealth and professionalism but 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 more prominent.

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

With light colors, you appear friendlier and more approachable.

So lighten up your capsule wardrobe and make an excellent first impression with light and soft colors.

Throw on a Blazer

Whether you’re dressing like an old-money gentleman o; a blazer is an excellent item in your closet 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 environment.

Therefore, having at least one formal blazer in your wardrobe is essential.

Try pairing your blazer with a dress shirt and tie for the classiest look. If you’re dressing like an old money aesthetic 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 various events.

It’s a great way to add visual interest to a plain outfit. It’s an excellent way to dress up a business 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 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 easy to wear and clean-looking. It’s an excellent option for both indoor and outdoor environments. 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 an excellent option for dressing casually during the day.

Classy Accessories like Timeless Watches

For the most part, you want to avoid wearing flashy 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 make you look too showy, watches are an excellent classier accessory to add to your outfit.

Choose a watch that compliments your outfit if you’re wearing a suit.

You can wear a more playful watch wearing a business casual outfit.

Regardless of your choice, make sure it’s appropriate for the occasion. It’s important to note that watches are an excellent 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, showing you’re willing to invest in your appearance.

Button Down Shirts

Button-down shirts are 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 ensure the first few buttons are unbuttoned. You’ll see This classic look on many old money gentlemen.

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

Tuck in your shirt, and it’ll look like you’re wearing a tie, but you don’t have to wear a link 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 traditional 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 attend an event with blasting AC. Simply pull a sweater over your shoulders.

Make sure it’s a neutral color, like cream or grey. It’s easy 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. You don’t want to wear jeans if you need to dress up for a meeting or want to look old money.

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

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

Wear Suit Pants

Suits are classic pieces of clothing that old money gentlemen wear.

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 appropriate for the season so you don’t get too hot or cold.

Suits are great 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?

The “Old Money Style” is a fashion aesthetic emphasizing 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 other modern brands like Mango and Luca Faloni also capture the essence of luxury old money.

Key garments of the Old Money Clothes 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 a Casual Chic Old Money Style. Men often opt for:

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

15 Key Elements of the Old Money Style

  1. Quality fabrics: Invest in premium materials, such as cashmere, wool, and silk, for your wardrobe. These fabrics stand the test of time and provide an understated elegance.
  2. Classic colors: Stick to neutral shades like navy, beige, and gray. These are versatile and create an instantly refined appearance.
  3. Well-tailored suits: Opt for well-crafted suits pants in timeless patterns, as they are a staple in any old money wardrobe.
  4. Blazers and sport coats: Choose high-quality blazers and sport coats in classic colors, adding sophistication to any outfit.
  5. Button-down shirts: Old money style revolves around traditional oxford shirts, which complete the gentlemanly look.
  6. Stripes and other subtle patterns: Incorporate subtle patterns like stripes, checks, and plaids in your wardrobe to add variety and depth.
  7. Luxurious accessories: Elevate your outfits with elegant accessories like silk ties, cufflinks, pocket squares, and dress shoes.
  8. Leather goods: High-quality leather items, such as brogues, loafers, and belts, help convey a sense of luxury and finesse.
  9. A preppy touch: Embrace the Ralph Lauren aesthetic by incorporating polo shirts, sweater vests, and other preppy classics into your wardrobe.
  10. Linen pants: Choose linen pants over jeans and sweatpants for a comfortable yet refined look.
  11. Understated elegance: Focus on minimal, clean lines and avoid flashy embellishments in your outfits.
  12. Well-groomed: Keep your hair, nails, and facial hair impeccably groomed for a polished aesthetic.
  13. Tennis and golf attire: Tennis and golf outfits can also embody the old money style through their elegance and grace.
  14. Heritage brands: Select garments from reputable brands with a strong history, such as Brooks Brothers and Loro Piana, to ensure top-notch craftsmanship.
  15. A capsule wardrobe: Finally, curate a selection of essential wardrobe pieces that work seamlessly together, allowing you to create a variety of stylish, sophisticated ensembles with ease.

Historical Background

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

In America, Old Money can be traced back to the Gilded Age, 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, which embodied a refined and classic sense of fashion. The Old Money look is about 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 students from affluent families frequented them.

Over time, the Old Money aesthetic evolved and adapted to include more contemporary elements while 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 essential, 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 famous for the “old money” style. 

How can men look expensive?

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

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 essential; a clean, polished appearance can exude confidence and sophistication.

What are old-money vibes?

Old money vibes are characterized by 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 certain behaviors and values, including discretion, refinement, and a focus on tradition and heritage. Old money families 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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Elisa S. is founder, author and blogger of Streetstylis who loves to write about latest fashion trends, celebrities and designer brands with their quality, price trends.
She has close to 3 years of experience in SEO and has taken the Streetstylis Pinterest account to one of the most popular magazines on Pinterest and Instagram.
When she's not working, you'll find her doing Pilates, dancing or hanging out with her friends in Malta.

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