How to Dress Like Old Money Men: As the old saying goes, clothes make the man.
And if you’re reading this article, you probably already know that being well-dressed goes a long way—especially in business.
But dressing like a modern gent isn’t easy for everyone.
In fact, most men struggle to find the perfect balance between professional and preppy. Fortunately, there are plenty of ways to dress like an old money gentleman without breaking the bank or giving up on your own personal style.
To help you embrace your inner blue blood, we’ve compiled some detailed tips on how to dress like a gentleman with Old Money style right now.
Read on and take notes…
Table of Contents
How to Dress Like Old Money Men
Keep it Classy with Light and Neutral Colors
When dressing like an old money gentleman, remember to stick with lighter colors.
Dark colors like black or navy blue are associated with both wealth and professionalism, but they 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 bigger.
Basically, you’re taking up more space than you need to, making you appear more aggressive and threatening than you really are.
With light colors, you appear friendlier and more approachable.
So lighten up your wardrobe and make a good first impression with light and soft colors.
Throw on a Blazer
A blazer is a great item to have in your closet—whether you’re dressing like an old money gentleman or 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 setting.
Therefore, it’s important to have at least one formal blazer in your wardrobe.
Again, a blazer is a great investment piece because you can wear it to a variety of different events.
It’s a great way to add visual interest to a more plain outfit. Most importantly, it’s an excellent way to dress up an outfit without being too stuffy.
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 own personal 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 both easy to wear and clean-looking. It’s a great option for both indoor and outdoor settings. 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 a great option for dressing casually during the day.
Classy Accessories like Timeless Watches
For the most part, you want to avoid wearing gaudy 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 can make you look too showy, watches are a nice classier accessory to add to your outfit.
If you’re wearing a suit, choose a watch that compliments your outfit.
If you’re wearing a business casual outfit, you can wear a more playful watch.
Regardless of what you choose, make sure that it’s appropriate for the occasion. It’s important to note that watches are a great 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, so they show that you’re willing to invest in your appearance.
Button Down Shirts
Button-down shirts is 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 make sure that the first few buttons are unbuttoned. This is a classic look that you’ll see on many old money gentlemen.
It’s an easy way to add visual interest to your outfit.
Simply tuck in your shirt and it’ll look like you’re wearing a tie, but you don’t have to wear a tie 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 classic 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 if you’re attending an event where the AC is blasting. Simply pull an sweater over your shoulders.
Make sure it’s a neutral color, like cream or grey. It’s an easy way 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. If you need to dress up for a meeting or just want to look old money, you don’t want to wear jeans.
Instead, try wearing suit pants or chinos. These are more formal and appropriate for work.
If you’re dressing like an old money gentleman, you can wear a blazer over the top of your pants to make your outfit stand out. But if you’re dressing for a casual work setting, you can simply wear pants.
Wear Suit Pants
Suits are classic pieces of clothing that is worn by old money gentlemen.
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 that’s appropriate for the season so that you don’t end up too hot or too cold.
Suits are a great option 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 Trend?
If you’re looking to dress more like an old-money gentleman, it’s important that you know the rules.
For example, you should always tuck your shirt into your pants. There are no exceptions to this rule. It’s a great way to keep your shirt tucked in, especially if you sit at a desk all day.
Moreover, it’s a rule that can be broken if you’re dressing like an old money gentleman. It’s important to know the rules before you break them.
How Do You Dress Like Old Money Man?
If you’re looking to dress like an old money gentleman, you’ll want to focus on three major elements: texture, color, and patterns.
Texture refers to the item that you’re wearing. Are you wearing a shirt, sweater, or tie? What kind of fabric is it? How does it feel against your skin? The texture is important because it helps to break up your outfit and prevents you from looking too boring. It’s an easy way to add visual interest to your outfit.
Color is another essential element of dressing like an old money gentleman. Remember, you don’t want to wear too many dark colors. Instead, try to stick to light, neutral colors.
*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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