7 Old Money Shoes Designs That Have ”Generational Wealth” Written All Over Them

by Stephanie Yankova

Thanks to TikTok influencers who have been voraciously pushing the trend, the Old money aesthetic has been on the rise. Based on the style of iconic figures like Princess Diana, the Kennedys, and Ralph Lauren, it’s become a symbol of high status and generational wealth. Of course, you don’t actually need to be an heir in order to look like one. You know what people say – ”Dress like the person you want to become”. Characterized by high-quality garments, tailored suits, Polo shirts, and other quiet luxury items, Old money has become more of an aesthetic rather than a lifestyle goal. I’ve always lived by a very simple fashion rule – invest in shoes and thrift the rest. After all, fashion is cyclical, but shoes – they’re a statement piece! Keeping that in mind, let’s dive into some of the essential footwear designs that have ”Old money” written all over them!

What are Old Money Shoes?

white loafers old money shoes oversized suit classic outfit ideas

Credits: modedamour

Old money style is based on simple, yet elegant and timeless unpretentious silhouettes. It’s all about the craftsmanship – try buying shoes made from high-quality materials like genuine leather, suede and nubuck. Stick to pastel shades and nude colors. And most importantly, learn how to keep your shoes clean – the muddy, worn-out look is definitely not in style! Here are some of the most iconic Old money shoes that will instantly bring a sense of effortless chic to your appearance!

Adidas Samba – The It-Girl Old Money Shoes

minimalist brown cozy oversized outfit adidas samba old money shoes


Credits: modedamour

Minimalist silhouette in a neutral colorway, which makes it incredibly versatile – this sneaker was released over 74 years ago and remains just as trendy to this day! In fact, this design might be even hotter right now than ever before! Celebrities such as Frank Ocean, Hailey Bieber, Bella Hadid, Kendall Jenner, and Jonah Hill are some of the biggest names in the industry who wear this shoe religiously. And truthfully speaking – celebrities are the modern-age royalties. Thanks to their superstar status these shoes have adopted the label of affordable luxury and are a staple piece in the Old Money aesthetic.

New Balance Tennis Shoes

new balance chunky dad sneakers old money shoes hailey bieber

Love it or hate it, the chunky dad shoes are here to stay for the foreseeable future! With the return of many of the 90s fashion trends, Princess Diana’s casual wardrobe has become a guidebook to street style. Whenever we think about what rich people do in their spare time, playing tennis is usually one of the first things that come to mind. The big New Balance sneakers are famously known for being one of the most comfortable sports shoes on the market and many figures of the Royal family have been seen wearing them over the years.

Classic Black Loafers

classic loafers old money shoes black and white outfit chic street style

Comfort, style and extreme durability – these are the three words I would use to describe one of my own personal shoes to ever exist! Truth be told, there’s nothing quite as chic as a nice pair of high-quality loafers that can so effortlessly elevate any look! A little tip – the simpler the design, the more expensive the shoe looks!

The Ballet Pumps

ballet flats old money shoes oversized black and white suit

Contrary to everyone’s fashion trends predictions, Ballet flats made their big comeback in 2016 and they’ve been becoming progressively popular ever since! Ballet has always been a performance art that gathers together high-status people, from celebrities to businessmen, politicians, and royalties. Quite self-explanatory, the Ballet shoe’s modern everyday wear design has become the epitome of Old money aesthetic.

Mary Jane Shoes

mary jane babydoll old money shoes white long socks

The Mary Jane pumps are a Preppy Style staple piece. Their design is so clean and unpretentious, that they’ve managed to remain fashionable throughout the generations for women of all ages and from all walks of life. A great way to style this shoe is by combining it with a pair of long or knee-high white socks, just like Blair Waldorf would do.

Grandma Heels

garndma heels old money shoes brown suede nude outfit casual elegant street style

Old money style is not about extremes, so whenever you’re thinking about what shoe to pair your fancy outfit with, a high heel is not the answer! The so-called Grandma shoe is all about comfort and practicality. These shoes are the perfect companion for the busy city girl who needs to go places and get things done, and wants to look fabulous while doing so! And the best part – they won’t make your feet burn from pain by the end of the day!

Riding Boots

riding boots old money shoes fall season essentials fall season outfit

Horse riding is one of the most graceful, exciting and soul-nourishing sports to ever exist, in my humble opinion. Not only are horses some of the most majestic animals, but the actual horseback riding attire is nothing short of pure perfection. It’s no coincidence that Gucci has released an entire collection inspired by Equestrian fashion. The most practical piece of the riding uniform is the boots! In fact, they are so comfortable and good looking, that royalties have oftentimes been spotted wearing them outside the arena.

Flat Mules

white mule flats old money shoes outfit ideas minimalist look

Backless shoes are undoubtedly becoming one of the biggest summer fashion trends. Celebrities such as Zoe Kravitz and Mary-Kate and Ashley Olsen are some of the main trendsetters when it comes to flat mules in particular. The Olsen Twin’s fashion house ”The Row” is famous for being one of the biggest modern time quiet luxury brands, so this shoe was quickly popularized as an Old money footwear essential.

Embedded image

Copy code to embed the image: Big picture: Small picture: BB-Code: