16 Old Money Clothing Essentials | Classic Style Capsule Wardrobe

Ah, the “Old Money Aesthetic”—where looking rich isn’t about having money, but about having a closet filled with the same ten items in different shades of beige. Timeless, sophisticated look that screams, “I summer in the Hamptons but haven’t checked my bank account since 2007.”

And folks, I am here for it.

First off, let’s address the elephant in the room:

No, dressing in “Old Money Style” does not mean you suddenly inherit a trust fund or develop an aversion to paying taxes.

This video makes it very clear that we are not trying to fool anyone into thinking we have generational wealth.

Which is a relief, because if my wardrobe could trick people into thinking I was rich, my landlord would have a lot of questions.

Now, onto the essentials.

We kick things off with…a cable knit sweater.

For summer. Nothing says “I have old money” like voluntarily sweating through a luxurious wool blend while everyone else is in tank tops.

But don’t worry, then they reassure us that even if we don’t live in a climate where July feels like a crisp fall morning in Nantucket, we can always “throw it over our shoulders”—which, let’s be honest, is the international symbol for I might own a yacht.

Next, we have collared shirts. Ah yes, the ultimate “I brunch with my polo club” staple.

They strongly discourage anything too fitted (too 2012) or too oversized (too Gen Z, ew), urging us to find the perfect, slightly relaxed fit. The shirt should say, “I care about my appearance, but not enough to look like I tried.”

This is the same energy-rich people give when they show up in linen pants and unbrushed hair yet somehow still look effortlessly chic.

Back to the essentials list:

• Jeans – But only straight-leg, because apparently, skinny jeans are out and wide-leg jeans are too in. We want timeless, not trendy, folks. Ideally, your jeans should look like you could comfortably ride a horse in them, even if the only horse you’ve ever been near is in a Ralph Lauren ad.
• Trousers – Because nothing says “I don’t need to work for a living” like wearing pleated pants to casual outings.
• Tailored shorts – Because sweating in trousers isn’t always classy.
• Little black dress – The secret weapon of every wealthy-looking woman. Pro tip: Pick one that allows you to breathe and sit down unless you enjoy looking elegant only while standing in extreme discomfort.
• Blazers – Necessary, even in summer, because rich people love to be slightly overdressed.
• Trench coats – You might not need one, but they’ll make you feel like an heiress escaping a scandal in the rain.

Now, let’s talk about shoes.

No, you may not wear your beaten-up flip-flops.

You need loafers or sophisticated flats. Why?

Because rich people do not scuff their heels in public.

Also, throw out your trendy puffed-up sandals—this isn’t a TikTok fashion challenge.

We’re here to look like we casually vacation in Capri.

Finally, accessories and makeup.

You must own pearls, gold jewelry, and of course, red lipstick. Why?

Because nothing says “I summer in the South of France” like a perfect red lip.

And if anyone questions your commitment to this aesthetic, just dramatically reapply it while saying something cryptic about “Daddy’s business dealings.” Works every time.

This was a masterclass on looking expensive while potentially being broke.

If you follow all the tips, you will look like you have a family estate somewhere, even if you’re eating ramen noodles in your one-bedroom apartment.

And that, my friends, is the true magic of fashion.

Bravo!