How to style old money outfits: A full-on guide

The old money style is all about that elegant and timeless look. The heritage of former generations and long-living traditions not only resembles their way of living but also their way of dressing. 

Generally speaking, old money likes to dress rather formally and elegantly but without the opulent details and looks you would assume. A great quote that describes the thinking of the old money style very well is:

Too many people spend money they haven’t earned to buy things they don’t want to impress people they don’t like.

Will Rogers

As old money is exactly the opposite of that shown quote, you can imagine that no shiny logos and big brand names will occur on their clothing. Rather you will find high-quality pieces of good craftsmanship. They will by far not be cheap or cheap looking but rather timeless and elegant.

To get a further understanding of how to style your old money outfit, we will give you a step-for-step guide in this article. 

Opt for a classic and timeless silhouette

When you start to put together your old money outfit, you will want to set the general look to a classic silhouette. This rather tight look will make a great appearance with old money clothes.

This classic silhouette will ensure you a timeless fit you can always wear. To ensure, you can achieve this classic silhouette, opt for the following clothes, for both men and women:

• Tailored blazer
• Button-down shirt
• Tailored pants
• A-line dress
• Wide-leg pants
• Crisp white T-shirt

Keep in mind that these clothes shall not be baggy. This also sets the base for layering which we will discuss later on.

Embrace elegance

One thing that goes in hand with classic and timeless silhouettes, is the embrace of elegance. You will want to put together an outfit, you can either go to a casual occasion with your well-off friends or attend a business meeting.

If you want to know more about casual old money outfits, check out my article about them here.

As a general rule, you will always want to dress up a little. This means you may be a little overdressed for a casual occasion but for a formal one, you may be perfectly dressed. It also helps to make sure, that a formal meeting could occur out of a casual occasion with your well-off friends and business partners. 

Opt for good craftsmanship and high quality

Another thing that helps you be elegant, is good craftsmanship and high quality. A good craftsmanship also resembles a great fit. Moreover, it will look sloppy if you dress up for any occasion and people can see poorly crafted clothes. Therefore, you will want to look out for the following things when choosing to buy your old money clothes:

• Look for continuous stitching
• Pattern matching
• Attention to detail
• Strings popping out
• Is it see-through?
• Durability
• Quality of material
• Brand reputation

If these criteria are fulfilled, the clothes may be expensive but you can ensure they will last a long time and therefore be more sustainable.

Choose timeless designs, no one-way-trends

One thing, trendy clothes are not most of the time is the previously mentioned sustainability. Also, quality is one main lacking aspect of trendy clothes. Old money is not at all about trendy clothes but rather timeless elegance. 

Not only are these poorly-made and mostly flashy clothes not trendy for a long time but also, they will not look elegant or timeless at all. Imagine going to discuss a deal regarding your family’s business and showing up in the latest Balenciaga joggers or something similar. 

Therefore, old money opts for timeless designs to also ensure the following step in our guide on how to style old money outfits.

Wear easily combinable clothes

What are the key elements when it comes to choosing easily combinable clothes? Firstly, old money doesn’t like big brand logos at all. Not only do they not represent the elegant and timeless aesthetic old money strives to gain. Also, they are not easily combinable at all, especially when you style old money outfits. 

To check out old money brands of any price range, read this article.

Another thing, old money doesn’t like is extraordinary patterns. For almost the same reasons as big brand logos, they are not practical and make you look like a show-off in the eyes of old money. 

So how do you actually find and wear easily combinable clothes? You will want to opt for basic items like T-shirts, button-down shirts, blazers, tailored pants, skirts, or sweaters that are of high quality and good craftsmanship. Also, they should be neutral-colored which we will show you what this means now.

Opt for neutral colors

Logically speaking, neutral colors are easily combinable, especially in comparison to bright-colored and bold ones. Therefore, old money favors them as they also make them look elegant. Neutral colors are:

• Black
• White
• Beige
• Grey
• Brown
• Navy
• Forrest green

As an example, you can choose black or blue tailored pants and combine them with a beige or white button-down shirt. Also, you can wear a grey or beige trench coat on top.

If you want some more outfit inspiration, check out my article about 27 old money outfits for men and women.

Choose natural fabrics

Another thing that makes old money clothes look elegant and timeless, is their natural fabrics. These natural fabrics are more durable and better for the environment. Natural fabrics you should use to style your old money outfits are:

• Linen
• Cashmere
• Cotton
• Silk
• Wool
• Tweed
• Leather

Just try to look at the fabrics when buying your old money clothes. They will make you look more elegant and blend in with the overall aesthetic better. 

Choose classic footwear

When you’re done choosing your clothes and combining them to match, it is time to finish the outfit with some classic shoes. As we know old money for simplicity and timeless designs, it is only logical to add shoes that will complement the outfit. Try to look out for neutral-colored shoes that don’t stand out too much. 

Some shoes to keep in mind for men:

• Loafers
• Boat shoes
• Oxford shoes
• White sneakers
• Chelsea boots

For women:

• Pumps
• Heels
• White sneakers
• Ballet flats
• Sandals

With these shoes, you can complement your outfit perfectly and achieve the old money look.

Accessorize with attention to detail

If you want to add the final touch to your outfit, accessorize carefully. Attention to detail is a key component of how to style old money outfits. Accordingly, we will do so with the accessories too. Therefore, you will want to look out for timeless and classic accessories, which are:

• Watches
• Plain necklaces
• Bracelets
• Rings
• Sunglasses
• Belts

For a more in-depth overview of old money accessories, check out my article about them here. 

You will then want to choose one or two from the above-mentioned accessories as too much will also not look good. Then, you want to make sure they are of good craftsmanship and high quality. When it comes to watches, you should opt for a leather strap or a plain metal wristband. If you can afford to, you can also wear watches like a Rolex but I wouldn’t wear any duplicates. 

As you want to style your old money outfits with great attention to detail, you can look out for matching jewelry or the color of the watchstrap matching your belt. Otherwise, just follow your instinct on what will look good and elegant.

Be well groomed

As you now finished styling your old money outfit, we will look at your hygiene and grooming. As old money will always be a put-together look, you will opt for good hygiene. Also, your grooming must be on point as appearance is one of the most important factors in business meetings.

Personally, I like to shave every third day to make sure I set the tone for an elegant outfit. If you wear a more voluminous beard, keep it trimmed well. For showering, I don’t recommend anything other than a daily shower. 

Embrace confidence

As you are now finished styling your old money outfit, there is just one thing to look out for before leaving the house. The key to the perfect old money look is confidence. Have you ever seen anyone considered to be old money walking around with a bent posture and a submissive look? Me neither!

So, choose clothes that will make you feel confident and ready to conquer anything that will happen to you today. 

Final thoughts on how to style old money outfits

This guide on how to style old money outfits has shown you detailed steps to follow when putting together your elegant and timeless outfit. If you follow these steps, there will be nothing stopping you from looking your absolute best. You may also soften this style up a little with contemporary clothes but keep the basics the same.