Old Money Style: How to Dress Like a Classic Gentleman

The year is 2024 but when it comes to fashion, the 1950s are making a comeback. While tech billionaires might prance about in t-shirts and jeans, most men interested in fashion aren’t satisfied with that approach to sartorial splendor. No, they want something more.

That’s why old-money style is making such a strong comeback. It exudes subtle luxury and timelessness that makes it suitable for today’s fashion-conscious man, even as the rest of the world seems to be moving in a less well-dressed direction.

But how do you adapt your wardrobe to meet old-money aesthetic standards? That’s what we discussed in this post. It explores how to dress in this inimitable style, including tips for effortlessly pulling it off.

Don’t Be Afraid To Be A Minimalist

The first step is to remind yourself that it’s okay to be a minimalist when it comes to . The era from 1900 to 1950 was one of simplicity and restraint where men dressed elegantly while avoiding excessive accessories or embellishments.

In this sense, minimalism isn’t a new movement. It is something that goes back many decades. Old money style avoids garish colors or loud prints in favor of subtle textures and neutral clean tones that tell a story of the man wearing them.

Recognize Tradition

Old money style also pays homage to tradition instead of trying to be avant-garde. It includes vintage pieces and even heirlooms where possible as a way to customize one’s look. For example, you might wear a ring or cufflinks passed down from one generation to the next in your family.

The more you can recognize traditional elements in your outfits, the more likely they are to sing. Adding these is essentially what differentiates old-money style from modern smart dress codes.

Use Classic Fabrics

Another pro tip is to use classic fabrics. Specific options like herringbone and tweed send out strong signals that you’re a classic man, looking to recreate styles from the early to mid-20th century.

Ideally, you should have a mixture of fabrics that change through the seasons (something men of the past would have rotated in and out of their wardrobes). For example, you could have heavier, warmer fabrics, like wool, for the winter, and lighter ones, like linen, for the winter.

These fabrics must look natural. They should reflect the materials available during the mid-century period. Cotton dress shirts and tweed blazers are ideal, but raincoats by Patagonia aren’t.

Keep Up Grooming Standards

It’s also essential to maintain top-tier grooming standards when dressing with old money style. Successful business owners and celebrities of the past always invested significantly in their physical appearance, ensuring it showed off their clothing in the best possible light.

Start by paying attention to your nails, ensuring you clip them short and remove any dirt and grime that might have accumulated underneath.

Polishing your shoes with a polishing set is also a good idea. These help them shine more and remove the dirt that can sometimes accumulate on them and make them look dull.

A good haircut and a trimmed beard also make sense. Many men of the past would have opted for clean-shaven, but this is not essential in today’s context as styles have changed.

Include Subtle Branding

Another tip is to incorporate subtle branding into your old money look. You don’t want to wear a printed tee. But it can be a nice touch to see luxury labels embroidered into cotton shirts or on accessories.

The key here is to make the logos subtle. This way, you can strike a balance between signaling wealth and keeping the attire as minimalistic as possible.

The good news is that most brands targeting the old-money fashion market do this for you. Ralph Lauren and Brooks Brothers include subtle elements that set them apart from most brands and make their designer names the focus.

Consider Your Outerwear

You also want to when going for an old-money look. During the winter a fitted trench coat can work well when paired with neutral tones. You can also try using an overcoat with proper lining. These add bulk to your appearance but also smack of style if used in the right way.

If you’re the sort of man who likes to live outdoors, Barbour jackets also make sense. These provide weather protection but also complement traditional aesthetics, creating the perfect balance.

Wear Sparkling Shoes

Shoes are perhaps the most challenging aspect of old-money style to get right, simply because the temptation is to choose modern brands. Leather should be the material of choice (because this was almost exclusively what men wore from the period in question). Oxfords and loafers were the most popular style, although brogues also gained currency during the period.

Most shoes of the mid-twentieth century were brown or black. However, other colors were sometimes seen in rare circumstances.

Suede was also sometimes a choice for environments. These give outfits a more casual look, though they may be less suitable for formal occasions.

Use Accessories That Hint At Luxury

Using accessories that hint at luxury is another powerful technique. You don’t want them to be obnoxious, but adding subtle elements can be extremely beneficial for your overall look.

For example, you can’t really go wrong wearing a high-quality watch. These focus on craftsmanship and function as a subtle display of wealth that many people will pick up on. You can do something similar for pocket squares and cufflinks. These also come in luxury variations worth exploring.

Avoid Bright Colors

Lastly, and perhaps more importantly, it is essential to avoid bright colors. Focus on neutral tones and shades, like white and beige, and avoid greens, blues, reds, and oranges unless you have an exceptionally good reason for using them.

Navy blazers can work in some situations, but you should be careful what you pair them with. You can also wear camel coats or an assortment of chinos, depending on your style.

So, there you have it: how to dress like a classic gentleman. Try it today.

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