13 best Old money shoes for a timeless appeal

Here, you can see a variety of old money shoes in a store.

Footwear is a very important element of any refined outfit and therefore, old money shoes are a crucial component of the old money style. With high-quality materials and a timeless appeal, the old money style offers elegant looks for everyone. So, let’s get into a guide about which old money shows to wear for any occasion.

What are old money shoes?

Old money shoes are a crucial component of every person’s timeless wardrobe. With a minimalistic approach, they can turn an outfit from casual to formal and level up the look immediately.

The most common old money shoes include:

  • Loafers
  • Boat shoes
  • Dress shoes
  • Elegant sneakers
  • Boots
  • Sandals
  • Pumps
  • Flats

These main types of footwear make the most common old money shoes. Underneath a small description of the essentials of old money shoes, you will find a detailed guide to any of those shoes and some more special ones.

Essentials of old money shoes

Before we jump into a detailed description of old money shoes, let’s first talk about the essentials any old money shoe has to have.

High-quality materials

High-quality materials are a crucial component of long-lasting great-looking shoes. Full-grain leather, suede, calfskin, rubber, and textile are great materials many old money shoes consist of. Make sure, those materials are of great quality and your shoes will last you for many years.

This picture showcases different colors of timeless shoes.

Neutral colors

To match the footwear with any outfit, old money shoes have to be neutral-colored most of the time. Therefore, the following colors are great examples:

  • Beige
  • White
  • Brown
  • Khaki
  • Black
  • Navy
  • Olive green
  • Gray
  • Burgundy

Additionally, some more colorful embroidery or fine lines on sneakers can also represent old money but generally, try to keep those colors neutral.

Timeless silhouettes

A well-fitting shoe does not only look better but also will make you feel a lot better. So, get to a physical store, and ask a sales associate to help you determine your size in the particular shoe. Maybe, he or she can also help you choose the perfect color. Brands like Ralph Lauren or Allen Edmonds offer great old money shoes.

Old money shoes for men and women

Now, let’s have a look at specific old money shoes for men and women. We will talk about prices, outfit combinations, occasions you can wear this shoe, and which colors it looks best at.


This picture shows a selection of Loafers, the most old money shoes.

Loafers are the pair of shoes I associate with old money the most. This timeless footwear comes in a variety of forms and colors. The loafers typically come in different styles. Penny Loafers, Moccasins, Tassel Loafers, and the very casual slipper loafer represent old money the best though.

Typically, you will find loafers to be casual to semi-formal shoes especially worn in summer or spring. Pair them with a timeless outfit like a combination of chinos and a sweater or an Oxford shirt.

For about $120 you should get yourself a stylish and high-quality loafer ASAP to boost your old money aesthetic. Typical colors like brown, black, or olive green are the best options here.

Boat shoes

Boat shoes are like the little brother of the loafer. The special trade of those shoes is their non-marking, anti-slippery sole that makes them a perfect fit for…well, boats. Suede and canvas are typical materials of boat shoes making them waterproof in terms of not damaging the material as compared to normal leather.

These rather casual shoes are the perfect fit for a yacht party with your well-off friends. Typically, you will wear those barefoot shoes with a casual outfit like a skirt, jeans, or chinos paired with a simple top or a polo or linen shirt. At a price of $100-$200, you can get yourself some high-quality boat shoes.

Dress shoes

From rather casual, we now take a step to the most formal old money shoe on this list. The dress shoe is a perfect fit for any formal occasion ranging from a business meeting to a black tie event. This timeless shoe fits great with a suit or a combination of chinos and a blazer.

To achieve a timeless look, opt for brown or black dress shoes made of high-quality leather. I prefer matt leather over shiny leather but this can be chosen according to the occasion and personal preferences. You can get yourself a great pair of Oxford shoes, a type of dress shoes for just $150 but brands like Allen Edmonds that sell high-quality ones start at $200.


Here, you can see some timeless boots.

When it comes to boots, various varieties complement old money perfectly. So, let’s look at some examples that will look great with the old money aesthetic:

1: Chelsea boots: Chelsea boots might just be the most common elegant boots. With a typically great fit and various opportunities to mix, match, and style them, the old money shoes are a must-have for any autumn or winter capsule wardrobe. Try to opt for black or brown ones with high-quality leather. You can find great Chelsea boots in various shoe shops starting at about $150.

For a guide on how to rock the old money aesthetic in the fall, check out my recent article here.

2: Chukka boots: This timeless footwear offers an even more formal appearance than the Chelsea boots. Typically, Chukka boots end just above the ankle and feature light brown as the main color. This timeless pair of old money shoes fits perfectly with a combination of chinos and a cozy sweater as well as an Oxford shirt. You can expect to pay about $200 or more for a nice pair of Chukka boots. They can be easily bought in retail though due to their great durability.

3: Riding boots: Riding boots are not only a crucial component of an old money activity but also make great fashion staples. Mostly used by women and on casual occasions, a nice pair of brown or black riding boots will look extraordinarily great. For a pair of high-quality leather riding boots, you can expect to pay about $300 to $500 making them the most expensive pair of boots on this list.

Elegant sneakers

This picture shows a pair of elegant sneakers from Ralph Lauren.

Elegant sneakers are a very underrated pair of modern old money shoes that fit a business casual or casual occasion’s needs perfectly. Typically, you can expect these shoes in combination with any old money casual outfit. From a sweater with some jeans or a chino to a blazer and blouse combined with some tailored pants…anything goes with these great old money shoes. 

Typically, I would opt for a pair of clean white sneakers made out of leather. Additionally, a thin line or a small lace at the back of the shoe that has a different color can add a little touch to the outfit.


In this picture, you can find some old money sandals: Espadrille Sandals, Roman sandals, Slipper Sandals, and Flip-Flops

Sandals are arguably the best old money shoes for women on a casual occasion in summer. With a light and minimalistic design and lots of ways to style them, sandals are very versatile and timeless. Here, we will look at the 4 most common types of sandals:

1: Espadrille sandals: Espadrille sandals are a casual pair of old money footwear that matches semi-formal outfits too. Due to their elegant and minimalistic designs with leather straps and small pearls, these old money shoes can work with an a-line skirt, a pair of chinos, and a blouse or button-down shirt perfectly. High-quality Espadrille sandals will set you back approximately $75-$125.

2: Roman sandals: You shouldn’t buy the first one you see when looking them up on Google, but some minimalistic Roman sandals do represent the old money aesthetic perfectly. With small straps above the foot and maybe up to the ankles, these old money shoes look stunning on any casual outfit. Don’t go for a pair where the straps range all the way up to the knee though as this will not look like quiet luxury. Opt for some high-quality brown ones for about $75-$100.

3: Slide sandals: When you hear the word slide sandals, please do not think of the latest Balenciaga sliders but rather about a timeless pair of leather sliders. These elegant shoes are perfect for a little walk in town or a day at the beach. For about $30 to $70 you can get yourself a great pair of them.

4: Flip-Flops: For a pair of flip-flops, the same principle applies as for the slider sandals. A neutral-colored pair of flip-flops with a leather strap will be a great fit for any beach day. Also, they are in the same price range for about $30 to $70.


Now, we will look at a very sophisticated pair of shoes. Some elegant pumps are the perfect old money shoe for almost any formal occasion for a woman. With a timeless appeal and smaller heels compared to other shoes, they elevate any formal outfit. Typically, you will want to wear them with an elegant dress or a combination of a pair of tailored pants or a skirt with a blouse and blazer. 

Typically held in colors like black, brown, or navy, these shoes should complement the outfit instead of being the main attraction. Therefore, neutral designs with rather small embroidery or décor elements fit the old money aesthetic perfectly. For about $200 you can get yourself some classic ones in the next department store. If you like them from a designer, expect to pay around $300 to $800.


For everyone who doesn’t like heels as much, we still have the classic flats as an alternative. With their feminine and timeless appeal, they make great footwear for formal occasions, especially in the office. 

Typically held in neutral colors just as the pumps, you may expect to pay about $100-$300. Also, you may experiment a little and include more colorful tones like light blue or turquoise to match certain types of outfits. Brands like Tory Burch or Tods offer incredible old money flats with a timeless appeal.

Final thoughts on old money shoes

As you can see from this article, many shoes can be characterized as old money. Typically, you can determine a shoe to match the quiet luxury aesthetic by its versatility, the use of neutral colors, as well as a great quality. 

Also, some shoes like rain boots or sports shoes are also worn by old money. They just do not match the overall aesthetic as well as the other ones in this list.


What are the best old money shoe brands?

Ralph Lauren, Tory Burch, and Cole Haan are the best brands for old money shoes.

What are the best old money shoes for men?

Loafers are the best old money shoes for men. Elegant sneakers and Dress shoes also offer a great use for men who dress old money.

What are the best old money shoes for women?

The best old money shoes for women include Flats, Pumps, and sandals.

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