The Art of Dressing Old Money: A Guide to Timeless Style

The ‘Old Money Fashion’ or  ‘Old Money Aesthetic‘ entails blending elements of classic American preppy fashion with contemporary relaxed silhouettes, resulting in a fashionable trend for men.

Prior to delving into the specifics of this style, it is essential to establish the ideal candidates for pulling off this look and determine the appropriate settings and seasons to embrace it.

This style is versatile and suitable for both warm and cold seasons. In warmer weather, you can opt for loose linen shirts, simple chino shorts and pants, and clean, minimalistic sneakers.

As the weather turns colder, layering becomes essential. Consider adding puffer vests and cashmere sweaters to your outfit.

Key Elements of Old Money Style

At its core, old money style is all about understated elegance. Instead of flashy logos and bold patterns, the old money elite prefer simple, classic pieces that are made to last.

One of the key elements of old money style is quality – when it comes to fabrics, accessories, and even shoes, the old money elite will always choose the best of the best. 

That means investing in pieces made from quality fibers like wool, silk and leather, as well as choosing well-made shoes and accessories that will stand the test of time.

Another important aspect of old money style is fit. Rather than opting for oversized or baggy clothing, the old money elite prefer pieces that fit them perfectly. This means investing in a good tailor – whether you’re buying a suit or a pair of jeans, having your clothes tailored to your exact measurements will give you a polished and put-together look that is essential to old money style.

Finally, old money style is all about confidence. When you’re wearing classic, timeless pieces, you don’t need to rely on flashy accessories or trendy patterns to make a statement. Instead, you can let your own sense of style shine through. Whether you’re wearing a well-tailored suit or a simple cashmere sweater, feeling confident and comfortable in your own skin is the ultimate hallmark of old money style.

How To Dress Like an Old Money Elite

The Key Elements on Dressing Like an Old Money Elite are:

• Minimal Logos: Old money elites typically avoid ostentatious branding or large logos.
• Classic Colors: Classic elegant outfit comes with classic colors.
• Custom Tailor: Ensure your clothing fits impeccably. Invest in custom tailoring or find a skilled tailor who can alter your garments to fit you perfectly.
• Classic Wardrobe Staples: Build a wardrobe around timeless pieces rather than following trends. Invest in high-quality essentials like tailored suits, blazers, dress shirts, and trousers in neutral colors like navy, gray, and beige.
• Accessories: Pay attention to the details. Accessories can elevate your outfit and showcase your refined taste.
• Fine Footwear: Choose high-quality classic leather shoes like oxfords, loafers, or brogues.
• Timepieces: A luxury watch is a common accessory among old money elites.

Best Brands For Old Money Style

Best brands for Old Money Style are:

• Ralph Lauren
• La Costa
• Loro Piana
• Jil Sander
• Canali
• Bode
• Brunello Cucinelli

Minimal Logos

Old-money style is all about classics. Always choose the clothes that have minimal logos and timeless histories in the brand, you don’t need to ‘flex’ with big-name brands that have their logo all over shirts.

Remember, focus on quality craftsmanship and subtle sophistication rather than conspicuous branding, as true class speaks for itself.

See Also: How To Dress Like Patrick Bateman

Classic Colors

Classic elegant outfit comes with classic colors. Most popular classic color choices for old money style are:

• Extra White
• Muted Green
• Muted Blue
• Ocean Blue
• Black
• Cream
• Beige
• Brown

Here are the most popular color matching choices:

Custom Tailor

If you really want to improve your fashion appearance, especially if you want to start dressing like old money men, there is no better option than getting a custom tailor that fits you perfectly. If you want to stay on a budget, find a highly skilled tailor who will know what clothes and colors will fit you perfectly based on your skin type and body measurements. Once you realize what works best for you and what does not, you can build a timeless wardrobe that exudes old money style.

Footwear: Quality Over Quantity

Quality over quantity! Roughly speaking, a good pair of shoes cost around $300 (basic Allen Edmonds as an example.)

In addition, we would then suggest you review your old pair of shoes. Decide if you have more wear and tear in a section of the shoe (typically either the toe or the heel) and install plates which cost practically nothing ($3). Now you will have a pair of shoes that will last *at least* 5 years.

Timepiece: Best Watch Brands For Old Money Style

Invest in quality watch! Best watches for old money style are:

• Rolex
• Cartier
• Casio
• Omega
• Audemars Piguet

The Keys to Finding the Perfect Old Money Watch

Building Classic Wardrobe: Polo Shirt and Chino Pants

Polo Shirts

When it comes to achieving the Old Money aesthetic, a timeless polo shirt is must for men. Whether it’s elegantly tucked in with a French tuck or worn all the way in, a polo shirt effortlessly elevates an outfit, exuding a polished look without appearing overly deliberate. Whether you opt for solid colors or stylish stripes, a polo shirt seldom disappoints, making it a reliable choice.

Chino Pants

The Chino pant, is a must-have in every guy’s wardrobe, remains a timeless essential that effortlessly embodies the Old Money aesthetic. Experiment with various fits, such as high-waisted or relaxed, but steer clear of overly tight or slim styles to prevent unsightly wrinkles or bunching.

Frequently Asked Questions