Old Money Style Men 2024: Outfits + How to Dress Like The Elite

#OldMoneyStyle for men, redefines classic fashion by amalgamating American preppy vibes with modern lines for an ultimate chic look. #timelessfashion #classicwithatwist.

Throughout this article, I’ll show you things like old money outfits men, how to dress old money men and some old money clothes men you need.

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
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03/18/2024 05:12 pm GMT

Old Money Style Men: 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.

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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.

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03/18/2024 06:02 pm GMT

Polo Shirts

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03/18/2024 05:47 pm GMT

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

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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.

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03/18/2024 05:42 pm GMT

You want to ensure the first few buttons are unbuttoned when wearing a button-down shirt. 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.

My Favorite Old Money Outfits Men You’ll Love too

Half Zip Polo Sweater

old money outfits men Half Zip Polo Sweater
by Pinterest

Polo Shirt Outfit

old money outfits men Polo Shirt Outfit
by Pinterest

Linen Outfit

old money outfits men Linen Outfit
by Pinterest

Linen Pants with Button Down Shirt and Sweater over Shoulders

old money outfits men Linen Pants with Button Down Shirt and Sweater over Shoulders
by Pinterest

Oversized Button Down Shirt

old money outfits men Oversized Button Down Shirt
by Pinterest

Suit Pants with Button Down Shirt

old money outfits men Suit Pants with Button Down Shirt
by Pinterest

Zip Wool Sweater

old money outfits men Zip Wool Sweater
by Pinterest

10 Old Money Accessories Man The Wealthy Wear

  1. Timeless Watches: A classic, high-quality watch with a leather or metal band. Brands like Rolex, Patek Philippe, or Omega are often favored.
  2. Leather Briefcase: A well-crafted leather briefcase adds a touch of sophistication and practicality to the professional look.
  3. Cufflinks: Simple and elegant cufflinks, often in gold or silver, can elevate a man’s attire, particularly when wearing a formal shirt.
  4. Monogrammed Items: Personalized accessories like monogrammed cufflinks, ties, or even a handkerchief can add a discreet and sophisticated touch.
  5. Quality Umbrella: A sturdy and stylish umbrella is a practical accessory that can also reflect a sense of refinement. Look for classic styles with a wooden handle.
  6. Classic Sunglasses: Timeless and well-made sunglasses, such as aviators or Wayfarers, are a staple for a polished look.
  7. Silk Tie: A high-quality silk tie in classic patterns and colors is a must-have for formal occasions.
  8. Leather Gloves: Fine leather gloves, especially in neutral tones like black or brown, are a practical and stylish accessory for colder weather.
  9. Cashmere Scarf: A soft and luxurious cashmere scarf can add a touch of warmth and sophistication to a winter aesthetic outfit female.
  10. Quality Wallet: A well-made leather wallet, preferably in a classic design and neutral color, is a subtle but essential accessory for any man.

15 Key Elements of the Old Money Aesthetic Men

  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 chic old money shoes mens.
  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.


Old Money Style Man

How to dress like old money man?

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 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 u0022old moneyu0022 style. 

What are old money brands men?

Old money brands for men include Rolex, Patek Philippe, Kiton, and Brunello Cucinelli.

u003cstrongu003eWhat are old money essentials menu003c/strongu003e?

Old money essentials for men include tailored suits, polished shoes, classic wristwatches, and high-quality dress shirts.

u003cstrongu003eWhat needs to be in a old money capsule wardrobe menu003c/strongu003e?

An old money capsule wardrobe for men should include tailored chinos, a classic white shirt, quality knitwear, a cashmere sweater, well-fitted jeans, and loafers for a timeless and understated style.

u003cstrongu003eHow to dress wealthy as a man?u003c/strongu003e

Dress wealthy by opting for tailored clothes, embracing accessories, investing in quality footwear, and choosing classy over flashy styles.

u003cstrongu003eHow do wealthy men dressu003c/strongu003e?

Wealthy men often dress in high-quality, tailored clothing, opting for classic styles with a modern twist, and accessorizing with luxury watches and leather goods.

Hu003cstrongu003eow to dress rich casual men’su003c/strongu003e?

Dress in dark, rich colors, layer with tailored blazers or sweaters over collared shirts, and choose high-quality leather shoes and accessories for a casual, rich look. 

*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 Steffes reviews designer fashion brands and elegant pieces for a living. She also loves Old Money Brands and is passionate about writing about topics related to this classic style.
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.


  1. Your insights into capturing the timeless elegance of the elite’s fashion are invaluable. It’s not just about clothing, but an attitude and sophistication. A fantastic roadmap for achieving this refined look! Love the blog!

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