How to Dress Like Old Money 

Forget fleeting trends and ostentatious logos if you want to exude timeless elegance. Embrace the old money aesthetic — a style that celebrates understated elegance and quality craftsmanship. This is for you if you wish to embody a look that whispers success rather than shouts it. Discover how to dress like old money for men and explore styling tips to achieve the aesthetic easily and confidently.

What Is Old Money Style?

The old money aesthetic represents a set of principles that have withstood generations. Today, it’s regarded as a fashion style that exudes understated refinement and timeless elegance. It’s the opposite of wearing flashy, branded clothes and accessories — old money is about embracing classic, well-tailored clothing. 

This aesthetic is widely associated with the upper class, particularly those with generational wealth. A-listers like Brad Pitt, Michael B. Jordan and David Beckham are some of the many icons of this fashion aesthetic. These celebrities may have different approaches to old money style, but they all have one goal — they don’t use flashy logos and excessive bling-bling to look stylish.

How to Dress Like Old Money for Men? 11 Essentials

The old money dress code resembles a capsule wardrobe —  a refined collection of clothing that can be mixed and matched to create many outfits. Here are the old money essentials to add to your wardrobe now.

1. Suits

A well-tailored suit is the foundation of the old money aesthetic. From modern slim fits to classic pinstripes, you must have suits that embody sophistication and elegance. Key elements include a tapered waist, well-fitted shoulder and pants that end just above your shoes. You can shop from your favorite brands, but nothing can beat custom-made clothing to ensure impeccable fit. 

Adding refined accessories like a tasteful tie or a silk pocket square completes your look. Ensure your tie is darker than the shirt but lighter than your blazer.

2. Blazers

Blazers are an indispensable piece of wardrobe. Wearing one with your favorite pants and shirt can significantly elevate your style from casual to smart casual. You’ll only need two main types of blazer — a single-breasted for more casual affairs and a double-breasted jacket for special occasions that don’t require an all-out formal dress code. 

3. Plain Shirts

No one can ever go wrong with a crisp, plain tee. The humble shirt has become a crucial part of any fashion aesthetic, with high-quality materials setting it apart from mass-produced alternatives. Opt for basic colors, like white, black and gray. You can also choose neutral tones you can easily pair with your bottoms.

4. Dress Shirts

A dress shirt has clean lines and a structured design, making it an excellent choice for smart casual and formal events. It’s a versatile piece that can complement suits, blazers and even your most basic pair of jeans. 

5. Polo Shirts

Premium polo shirts scream casual sophistication. They combine comfort and style in a refined way. A polo shirt is best worn during brunch with your significant other, a Sunday golf game with your friends, an out-of-town trip, or visiting your niece’s birthday party. Just ensure it’s not too loose or tight so you can perform your outdoor activities well. Pair it with tailored pants, jeans or shorts for that casual elegance.

6. Lounge Wear

Lounge shirts are comfortable enough to wear at home and well-presentable for casual affairs, such as beach parties, grocery shopping and even dates. They are made of breathable materials to keep you comfortable, no matter the weather. Long, loose shirts, long sleeve Henleys and cardigans fall within this category.

7. Dress Pants

A pair of dress pants can be paired with almost any top. Wear it with a dress shirt for corporate meetings, or match it with a crisp white tee for that smart casual appeal. Opt for classic hues like charcoal gray, navy, black and brown. Wear leather dress shoes like monk straps or classic white shoes to nail the look.

8. Shorts

Men with old money style can wear shorts, too. Opt for classic chic shorts, such as pleated or straight shorts. A well-fitting pair will give you elegance during a boat day or a casual event under the sun. Breathable materials like linen can provide comfort and style.

9. Chinos

A pair of chinos can take you from daytime to evening without feeling icky. It provides the right type of comfort while keeping you all dressed up for any event. Choose classic colors like black, gray and khaki. A good pair of chinos must pass the scrunch test — ball a section up in your fist, hold it for 10 seconds, release and check if it stays wrinkled. If so, rethink your purchase.

10. Slim-Fit Jeans

Denim is also a staple in your old-money wardrobe. Choose pairs that offer comfort, quality, a superior fit and subtle detailing. Keep an eye out for details like pockets and buttons and a streamlined silhouette without much branding. The classy deep grayish-blue color pairs well with almost everything, like an unstructured blazer or cashmere sweater.

11. Tech and Traditional Accessories

Your accessories can make or break your look. Sleek, modern ones like the Bang & Olufsen Beoplay H95 Headphones are an excellent tech-forward addition to your aesthetic, especially when you want to drown out background noise or mentally escape from an awkward situation. Traditional accessories like a leather suitcase or Tom Ford’s Block Square Eyeglasses add a hint of intellectual chic to your outfit.

3 Old Money Brands for Men

Are you wondering what brands people with old-money aesthetics wear? Whether you’re searching for where to buy old-money clothes or upgrading your wardrobe, these brands will provide you with the essentials.

1. Carissimi

This Scandinavian luxury clothing brand combines minimalist design with premium craftsmanship. It mainly offers knitwear made from high-quality merino wool. 

2. Ralph Lauren

Previously Polo Ralph Lauren, this brand is hailed as one of the best American fashion brands. It draws inspiration from old Hollywood glamour, country club sophistication and Ivy League elegance. Get your polo shirts and premium shorts from this brand.

3. Canali

Canali offers understated luxury items, including blazers, jackets and knitwear. Its appeal lies in Italian craftsmanship and impeccable tailoring, which result in clothes that blend contemporary and classic styles. This brand is perfect for embodying stealth wealth without flashy branding.

Embrace the Old Money Aesthetic Today

Mastering this style is an investment in your present and future self. Since embracing the old money style requires purchasing costly but quality essentials, it’ll last a long time. Embrace that quiet confidence and appreciation for quality for years to come.