The Old Money Style Guide: What is it and how to wear it

If you have been on TikTok lately, there’s a chance you’ve come across a trend known as the “Old Money” aesthetic. That chance increases exponentially if your search history is dotted with the likes of “Quiet Luxury”, Princess Diana, après-ski style, Ralph Lauren,  J  Crew, and any delegation of the Kennedy family.

But what exactly is the “Old Money” style? To understand the aesthetic, one need to look no further than the timeless styles of Jackie-O, Paul Newman, and Lady Diana.

The trend places a focus on quality, logo-free designer pieces, tailoring, and classic American prep. But despite it’s vintage feel, there are plenty of celebs that have been inspired by the Old Money style – like Sophia Richie, Gwyneth Paltrow, and Blake Lively.

Compared to TikTok trends inspired by Y2K or 90s style, the core of the “Old Money” trend is just that, old. It is a way of dressing that’s inspired by the inherited wealth of yesteryear’s most famous family dynasties, like the Kennedy’s, the Getty’s, and the Vanderbilts.

The hashtag #OldMoney has amassed more than 446.7k posts on TikTok to date and includes bite-sized explainer videos of famous families, east coast versus west coast wealth, and, of course, how to style the “Old Money” trend for both men and women.

While the origins of the trend may be based on decades-old traditions and wealth beyond imagination, styling the Old Money aesthetic doesn’t require a nine-figure bank account.

For Old Money flair with a new, I-don’t-have-money-but-I-want-it mentality,  check out our outfit ideas and style tips  for both guys and gals to master the trend.

If you’re looking for outfit inspiration for the Old Money aesthetic, then you’ve come to the right place. Let this be your starting point on your journey, where you can gather ideas for how to give off Old Money vibes (fake it ’til you make it, amiright?).

• Start by following the IG accounts of people who have an Old Money aesthetic. A few of our favorites are Lana del Rey, Julia Roberts, Jennifer Lawrence, or Victoria Beckham.
• Watch films and TV series that have an Old Money style. You can find some great outfit inspiration from movies like Cruel Intentions, Breakfast at Tiffany’s, or the more recent hit blockbuster, Challengers. You can also look to Blair Waldorf’s style in Gossip Girl for even more Old Money outfits.
• Read up on your Old Money style icons. What better place to get inspiration than to look to the original icons of the aesthetic. You can easily get an idea of the “Old Money” vibe by looking at pictures of people like Jackie Kennedy, Carolyn Bessette Kennedy, Princess Diana, or Grace Kelly.

The Old Money style is such a classy and put together vibe it’s no wonder that it’s such a popular aesthetic. But coming up with Old Money outfit ideas for men might not be so easy. So to make your look seem effortless, here are some tips on where you can find style Old Money style inspiration for men.

• Follow celebrities that have an Old Money style. Some good examples are Shawn Mendes, Jacob Elordi, Jude Law, George Clooney, and Austin Butler.
• Rewatch some classic movies that have a preppy, Old Money vibe. Have a movie night and watch timeless films like The Talented Mr. Ripley, Casablanca, or The Great Gatsby. 
• Get yourself familiar with Old Money icons like John F. Kennedy Jr., James Dean and Marlon Brando. A lot of their looks are still just as fashionable today, so you can’t go wrong if you steal their style!

So what are the key style elements of the Old Money aesthetic? Here are some essentials that you can be your foundation, with these fashion pieces you can start to build your Old Money capsule collection.

• Blazers: A blazer is one of then most iconic pieces fom the Old Money aesthetic. It can elevate a jeans outfit (take it from fashion icon Princess Diana) or be worn with a chic knee-length skirt and pull-over for relaxed but still put-together look. Go for a longer, oversized cut to give your outfit a more vintage look.
• Knee high leather boots: If you really want to commit to the look, try a pair of leather knee high boots. The look is timeless – proven by how good it looks on Diana in the 90s and Emily Ratajkoswki in the present day! These are boots are super versatile and can easily be mixed and matched – with a classic college sweater, or chic rollneck top, or even just a basic white t-shirt.

• Trench coats: Another key piece of the aesthetic is the trench coat. The perfect piece of outerwear for summer, fall, and winter – you’re sure to get your money’s worth from this item.  The trench coat definitely has a  history – it was said to have been invented by Burberry during WWI! With that kind of legacy – it’s a pretty strong fit to the Old Money aesthetic.

• Tailored basics: Nothing says Old Money more than tailored basics. The aesthetic is all about clean lines and understated elegance.  When selecting your basics think about items that can be easily worn with a variety of looks. We love a beautifully tailored pant that has the right amount of fit without being too tight. Or perhaps a suit vest – which pairs perfectly with a basic t-shirt or simply worn by itself on breezy, summer days.

If you’re still not sure what to wear when it comes to the Old Money style, check out these style essentials that are sure to “prep” you for your days at the country club.

• Loafers:Let’s face it, nothing says class like a chic pair of loafers. Pair them with a straight-fit chino pant and a smart blazer and you’re all set! They’re usually worn without socks (or at least no-show socks), but if you’re looking to spice up your look, wear them with a pair of brightly colored or patterned socks.
• Blazers: As for the blazer, go for a classic black or blue or switch things up a bit with a neutral print like tweed or houndstooth. Not sure what to wear underneath? Keep it casual with a basic white t-shirt or a crewneck sweater – or go more formal with a polo shirt or button-up shirt.

• Polo shirts: A classic polo shirt is a must-have for men when it comes to the Old Money aesthetic. Usually styled with a French tuck or all the way in, a polo shirt can make an outfit look put together without trying too hard. Solids or stripes, its hard to go wrong with a polo shirt and pair of smart, straight-leg trousers.

• Sweater vests: If you really want to capture that Ivy league-vibe that comes with the Old Money aesthetic – it’s time you threw on a sweater vest.  It’s a casual look – but done in a chic and relaxed way. Wear it with a pair of jeans or chinos.
• Chino pants: Ah the chino pant – wardrobe staple that every guy should have at least one of in their closet.  It’s a timeless piece, which is why it fits so perfectly to the Old Money aesthetic.  Feel free to play with different fits, (high waisted or a more relaxed fit) just avoid going for something that is too tight or slim fitted, as this can lead to unwanted wrinkles or bunching.

Now that you know what your style essentials are to pull off the Old Money aesthetic, where can you find them? Brands like Tommy Hilfiger, Lacoste, and Polo Ralph Lauren are a great place to start. They have great basics and staples that fit perfectly to this aesthetic. While they have all modernized a bit in the past years, they still maintain their “All-American” preppy roots.

If you’re looking for basics to go with your Old Money style essentials, brands like GAP, Uniqlo, COS, and Arket are a great place to look!

So now you have all the tools – where you can find outfit inspiration, which pieces to buy, and where to find them. Here are some final Old Money style tips that will bring your look together!

• Fit is key.The style is all about loose-fitting, but still tailored items. Nothing should be too tight or “too modern”. Avoid anything cropped or body-con, and rather go for a more oversized or loose cut.
• Monochrome or duo-tone is best. What makes an outfit look instantly chic? Monochrome. Avoid combining too many colors together. Some great color combos are blue and white, red and white, or blue and brown!
• Choose retro prints. The Old Money aesthetic is all about this retro-feel so if you do go for prints, let it be ones that reflect the “old-school” style- like stripes, polka dots, and houndstooth.
• Don’t forget accessories. Don’t underestimate the power of good accessories. Classic Ray-Bans, a cool baseball cap, a canvas tote, or a elegant watch could be just what your look is missing.
• Avoid “logo-mania”. Old Money is all about subtlety, so avoid logos or designs that flaunt or “scream” wealth.
• Quality over quantity. Invest in quality pieces that you can wear again and again and combine with several looks rather than “fast fashion” items that quickly lose their style appeal.