Old Money Aesthetic: How To Dress Rich and Look Expensive

how to dress old money and look expensive and classy

Want to learn how to dress old money? The classic old money aesthetic has been popular in fashion for decades, and it’s a staple style for how to dress rich and look expensive.

The look is classy and elegant, one that instantly makes you look well-to-do. It’s equal parts Ivy League academic preppy, and American country club, with a sprinkle of equestrian sporty.

“Old money” style is timeless and often the way upper-class people tend to dress.

If you want to learn how to dress rich and look expensive, read our guide all about the old money aesthetic.

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The old money aesthetic is a style that takes cues from classic Ivy League academic style but with a modern twist. The result is a chic, sophisticated look that feels both new and timeless.

It’s the perfect blend of comfort and elegant style.

Think blazers, tailored trousers, tennis-inspired outfits, polo shirts, oxford button-ups, collars, pleated skirts, simple pumps, white runners and classic loafers.

Although the look has been around since the 1920s, and has never been out of style, it is gaining a lot of popularity right now.

How to dress old money: outfits ideas to try
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How to dress old money aesthetic: preppy outfits ideas
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One of the best things about the old money look is that it can be easily achieved.

In fact, most of the items you need can probably be found in your closet!

If you are working on glowing up and shifting into your desired reality, and are looking for a new style to suit the new you, the old money aesthetic is perfect!

Old money style fashion ideas
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Old Money Aesthetic: How To Dress Rich and Look Expensive

You can put together an old money capsule wardrobe with a bit of creativity.

What Does “Old Money” Mean?

When someone is “old money” they are said to have inherited their wealth, rather than worked for it.

The term “old money” has been used in fashion to describe an aesthetic of dressing classy like someone with generational wealth does.

How do you make an Old Money Aesthetic Capsule Wardrobe?

The key to putting together an old money capsule wardrobe is to invest in timeless pieces that can be mixed and matched to create multiple outfits.

When it comes to materials, look for items made from natural fibers like cotton, linen, wool, and silk. The colors are typically neutral, such as black, white, grey, and navy.

The clothing is also generally simple and sleek, without frills or embellishments. An old money capsule wardrobe typically includes items such as a blazer, a button-down shirt, a cardigan, a dress, a skirt, trousers, and flats.

This type of wardrobe is perfect for those who want to look stylish and put-together without looking too formal or overdressed. Stick to a color palette. When creating an old money capsule wardrobe, less is more.

That’s why it’s important to stick to a small color palette when choosing your clothing items.

I recommend sticking to neutral colors like brown, white, cream, navy, beige, neutrals, and grey.

This will help create a cohesive look that you can easily mix and match.

Here are 17  Clothing Pieces You Need To Nail The Old Money Fashion Style

What clothing do you need to achieve the old money style? You’ll need a few key pieces to get the look just right. Here’s how to do it…

1. A Button-Down Shirt With a Collar

The first clothing item you’ll need for an old money wardrobe is a button-down poplin shirt. Preferably, the shirt should have a collar, but it doesn’t have to be super formal.

How to dress old money - classic poplin shirt copy
Source: J.Crew

Short-sleeved or long-sleeved shirts will work depending on your preferred style.

2. Sweater vests

A sweater vest completes the old money look any time, any day, and it is the perfect add-on to give that academic vibe. They can be worn over a collared shirt or a t-shirt for a more casual look.

Verdusa Women’s Button Front Striped Collar Sleeveless Sweater Vest Knit Top Black S
  • Soft fabric has some stretch
  • Collar, Sleeveless, Striped Trim, Colorblock, Button Decor, Knitted Pullovers Vest
  • Perfect to dress with your blouse, button up shirts, skinny pants, shorts, skirt and jeans
  • Suitable for dating, weekend, street, school, shopping and dailywear
  • Please refer to size guide carefully before purchasing at below description

And they come in all sorts of colors and patterns, so you can definitely find one that fits your style.

Plus, when the weather gets cold, they are the best way to stay warm without sacrificing style. I love this cotton summer sweater tank in caramel

3. Cardigans

old money aesthetic cardigan
Source: J.Crew

You’ll need a cardigan or two (or three) to achieve the old money look.

Cardigans are essential for layering, and they can make an outfit pop. Cardigans are another must-have piece for this style, like sweater vests.

To nail the old money look, go for a cardigan in white, light brown, or beige colors, and of course have a one in black/beige stripe, or navy blue/beige stripe.

old money fashion striped cardigans copy
Source: J.Crew

I am absolutely obsessed with the Emilie patch-pocket sweater (pictured above), a striped cardigan with gold buttons.

Here’s a similar cardigan I found on Amazon:

LILLUSORY Women’s Striped Cardigan Sweaters Chunky Knit Dressy Casual Black and White Cute Tweed Jackets 2024 Trendy Long Sleeve Button Cashmere Knit Blazer
  • 【HIGH-QUALITY MATERIAL】The knit cardigan sweaters for women feature skin-friendly and buttery-soft fabrics which provide long-lasting warmth and an ultrasoft feel. Thanks to the great elastic, the womens cardigan sweaters perfectly is suitable for most figures

4. Turtle necks

Stick to neutral color turtle necks for your old money capsule wardrobe. They are perfect for layering under blazers and cardigans.

You can also wear them on their own with a pair of high-waisted trousers or a skirt.

5. Sweater tied around Your shoulders

There is a reason why characters in movies who are supposed to be posh and well-off are usually costumed with a sweater tied around their shoulders.

It just screams country-club chic!

You will want to pick up a few cable-knit sweaters. They are the epitome of cozy chic. They are warm, stylish, and versatile. And they go with just about everything, which makes them perfect for an old money capsule wardrobe.

When picking a cable knit sweater, stick to neutral colors like black, white, cream, or grey.

6. Trench Coat

I love a good trench coat; they add a certain level of sophistication to any outfit and they are perfect for transitioning from fall to winter. To get the old money aesthetic, go for a trench coat in beige, camel, or brown trench coat.

Source: Stella McCartney

The Iconic Trench from Stella McCartney is an old money wardrobe staple. Pair this with a cute pair of boots, and you’re good to go.

7. Blazers

Blazers are the most versatile clothing piece for any capsule wardrobe. A plaid, brown, or cream blazer is perfect for layering over a button-down shirt and sweater vest.

Or you can go for a black blazer to wear over a bodysuit or plaid dress.

Complete this look with Mary Janes, loafers, or boots. I love this trailblazer belted blazer from Aday in classic latte color

8. Bodysuits

Bodysuits are another versatile piece that can be dressed up or down. And they are perfect for layering under blazers, cardigans, and trench coats. Wear a white, pastel, or cream bodysuit.

MANGOPOP Women’s Mock Turtle Neck Long Sleeve Tops Bodysuit Jumpsuit (A Long Sleeve Black, Large)
  • MATERIAL: Crafted from a luxurious, soft, and elastic fabric, this long sleeve bodysuit offers women a delightful tactile sensation and exceptional comfort.
  • DESIGN: This form-fitting, womens long sleeve tops features a turtle neckline and soft fabric that contours to the body, enhancing the overall fit.
  • SNAP CLOSURE: Equipped with two buttons at the crotch, this bodysuits for women ensures stability and provides convenient access for bathroom visits.
  • SEAMLESS CUTTING: Employing high-end seamless cutting technology, this turtle neck bodysuit boasts a flawless construction that enhances both comfort and aesthetics.
  • FLAWLESS FITTING: Prior to placing an order, please refer to our size chart to ensure a comfortable fit when wearing the bodysuit.

You can also find bodysuits with lace details or ruffles for a more feminine touch.

9. Polo Shirts

Every capsule wardrobe requires a couple of T-shirts, but an old money capsule wardrobe can not be without the polo variety.

Short sleeve Polo shirts are always a good bet, but I’m really loving this long sleeve version too!

How to dress rich: wear a long sleeve polo shirt
Source: For Days

10. High-waisted trousers

High-waisted trousers are a must-have for any old money capsule wardrobe.

Why? They are super versatile. Go for high-waisted trousers in black, cream, beige, or brown. You can also find them in plaid or stripes if you want to add a little pattern.

Wide Leg Dream Pants [Shop]

Way High Drape Pants [Shop]

The TENCEL™ Relaxed Chino [Shop]

11. The Right skirts

Pleated skirts are the perfect mix of preppy and classic, exactly what the old money style is all about.

Plaid is a must-have color for any classic wardrobe so it’s no surprise that it made it on this list.

Corduroy skirts are another must-have, as they’ve got a vintage feel and are super comfortable. Corduroy skirts can be dressed up or down like pleated skirts, making them versatile enough for any occasion.

I love a white knee-length corduroy skirt with a slit at the front.

The most important thing to remember when styling a skirt in an old money look is to be aware of its length. Knee length or slightly above or below the knee is appropriate for this aesthetic. Micro-mini skirts, however, have no place in this style!

The only time a short skirt is worn is if it’s a tennis skirt, and even then, it should never be above where your finders end when standing.

12. White Chino Shorts

There is something just so cool about white chino shorts with a tucked-in button-up shirt.

It’s a classic outfit staple in the old money aesthetic. Pair it with a skinny brown belt of course!

why white chino shorts make you look expensive
Source: J.Crew

13. Puff sleeve tops

Puff sleeve tops are back in style and perfect for tapping into the old money aesthetic.

Wear a puff sleeve top in white, cream, or pastel colors. You can also find them in striped or plaid patterns. Wear them with your high-waisted pants or plaid pants to give you the perfect styling.

14. Silk Scarf

A silk scarf tied into your ponytail or around your neck is a ladylike vibe that is totally old money.

15. Skinny brown belt

An essential accessory is the skinny brown belt!

16. Old Money Style Shoes

There are a few types of shoes you will need, to tie your new old money capsule wardrobe together.

  • Round-toe pumps with a low square heel
  • Clean white tennis shoes
  • Knee-high riding boots
  • Flat sandals.
  • Oxfords
  • Loafers

The shoes you choose will play a significant role in determining the overall tone of your outfit.

17. Chic Handbags

Achieving the perfect old money aesthetic look isn’t just about nailing down the right clothing items; it’s also about having the right accessories.

And when it comes to accessories, there is no piece more essential than a great handbag.

Not only will a crossbody bag hold all of your essentials but it will also free up your hands so you can carry coffee mugs, umbrellas, and whatever else life throws your way.

Classic old money outfits for women
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Putting It All Together:

Start with a pair of beige trousers, brown belt and a white button-down shirt. Then, tie a sweater around your shoulders, in a neutral color like beige, or striped beige/navy.

Finish off the look with a pair of Mary Jane shoes or classic Oxfords. If you want to improve the look, try adding a pretty scarf or statement necklace.

How To Look Expensive (And avoid looking tacky)

Before we dive into the types of old money aesthetic clothing you’ll wear, we first need to cover the basics of how to look expensive.

And you may be surprised to learn that the trick to looking expensive is more about what you do, and less about what you wear!

Wealthy people put effort into how they present themselves, beyond just the clothing they wear.

If you want to look expensive, ensure that you do these 20 things:

Tailor your clothes

Tailoring your clothes will make a big difference.

Present yourself with confidence

You can wear the nicest clothing in the world but if you don’t ooze confidence, it won’t look right! Work on your confidence so you can shine in and out.

Wear simple jewelry

Less is more when it comes to jewelry. Simple gold studs, a watch or a bracelet is all you need.

Wear subtle makeup

Too much makeup makes anyone look low-class and tacky. Women who look rich keep it simple with makeup in neutral colors that enhance one’s beauty, not overtake it.

Tuck in your shirt

An easy, free way to look expensive is to simply tuck in your shirt!

Steam your clothes

You could be wearing a $10 shirt or a $100 shirt and neither will make you look expensive if they are wrinkled. Steam your clothes!

I love my Kexi travel steamer!

Handheld Steamer for Clothes, Kexi Portable Travel Garment Steamer with 1200W Powerful, Lightweight Fabric Steam Iron for Home and Travel
  • POWERFUL CLOTHES STEAMER: Powered by 1200 W with steam flow 25g/min that soften the fabric and remove wrinkles. The effectively handheld garment steamer is ready-to-go water tank heats in 40 seconds and powers 12 continuous minutes of soothing steam.
  • SMALL & HANDY, EASY TO USE & SAFE: Get our foldable and portable handheld travel steamer with lightweight 1.67lb and enjoy the hassle-free traveling. Suitable for home, office and travel. Easy to store in any suitcase. Manufactured under strict safety guidelines. Extended 70ft ultra long cord for added convenience.

A crisp white oxford / button up goes a long way

Have a few in your capsule wardrobe.

Women’s Relaxed Oxford Shirt


Women’s Relaxed Oxford Shirt


Invest in quality fabrics

Another trick to looking expensive is to know that its not about designers or name brands, it’s all about quality fabric.

Invest in pima cotton, organic cotton, cashmere, and wool.

Read: Why wearing organic cotton actually raises your vibration.

Stick to a clean, calm color palette

The old money aesthetic is “quiet luxury” after all. Avoid loud/crazy prints.

Always wear clean shoes

Want to look poor? Wear old, dirty scuffed shoes. People with money take care of their shoes, and don’t leave the house in dirty footwear or heels with scuff marks

Size up

When in doubt, always size up when buying clothing. Too small fits will look tacky, whereas clothing with a bit of looseness will look chic.

Avoid logos

Did you know that when designers sell clothing with their logo all over it, those clothing lines are specifically made for broke people? It’s true!

Clothing with visible brand logos are only ever purchased by broke people who think it will make them look rich. When in fact, actual wealthy people would never walk around looking like a walking billboard for someone else’s company!

Avoid logos, and stick to classic, timeless pieces made from high-quality fabrics if you want to look expensive for real.

Wear perfume

As you glow up into the new, classy version of yourself you should have a signature scent.

Take a friend to the perfume counter and try a few different blends to find the right scent for you. A perfume that suits one person won’t suit everyone so take some time to figure out your ideal scent.

Have white teeth

A bright white smile is a must if you want to look expensive.

Book yourself into regular cleanings at the dentist, brush and floss several times a day, and use mouthwash regularly.

If you have yellow stains, use white strips or have your teeth professionally whitened.

go for classic, over trendy

I’ve made the point about “quiet luxury” a few times but it is so important.

Wealthy people may try out a trend here and there for fun, but they are not tethered to chasing trends. Instead, they invest in timeless, high-quality pieces that will last a lifetime.


Create a skincare routine and stick to it!

The Right sunglasses

If you want to look rich, avoid cheap-looking or wacky-styled sunglasses, and stick to well-made sunglasses in classic styles.

The Quality of A Handbag Matters More Than The Label

Read that again!

Preppy and posh old money style tips for how to look rich
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Frequently Asked Questions About How To Dress In The Old Money Aesthetic

What are the best Old Money Fashion Brands? where to buy old money clothes?

Ralph Lauren, Lacoste, Banana Republic, Polo, J.Crew, Club Monaco, Abercrombie, GAP, Everlane.

What Are The old money aesthetic accessories?

The old money style calls for quiet luxury. Simple, classy gold jewelry, a watch, a subtle handbag, and sun sunglasses is all you need. Avoid costume jewelry, wild colors or anything with a loud print.

What Are The old money aesthetic hairstyles?

For women, any neatly trimmed hairstyle can work for the old-money look. A shoulder-length bob with a headband is a classic look, as well as a high ponytail. Just avoid unkept/messy hair or straggly ends.

For men, keep hair cut short, or short on the sides and a bit longer at the top.

What Do You Need For An old money aesthetic Summer Wardrobe?

With all the sweaters, sweater vests and trousers you might think the old money look only works in Fall/Winter or on the East Coast.

But actually, the old money look can be achieved with ease in Spring/Summer and warmer climates! Swap the pleated trousers for pleated shorts and skirts, and wear light linen tops.

How do you get that “Old Money Glow”?

To get the visible appearance of radiant, healthy, glowing skin like so many wealthy people have, you need to take good care of your skin, and your body overall. Use organic, all-natural skincare products, eat healthy, and avoid toxins (alcohol, smoking, processed foods, non-organic foods).

Old Money Aesthetic: How To Dress Rich and Look Expensive – Conclusion

With these 17 key clothing pieces, you’ll be well on your way to nailing the old money aesthetic. And once you’ve got your hands on the right pieces, putting together outfits will be a breeze.

So what are you waiting for? Start shopping!

Young woman at the races, showing how to dress old money.
old money aesthetic - How to dress old money and look expensive
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