How to Dress Like Old Money: 22 Clothing Items for an Old Money Wardrobe

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If you have been following fashion trends recently, you may have come across the old money aesthetic!

For anyone new to the old money fashion scene, it’s all about those looks that scream class without trying too hard. These outfits just naturally have that rich, cool feel.

When shopping for your new wardrobe, you may wonder which pieces you need to achieve this look.

This post will show you how to dress like old money, with 22 pieces that will give your closet that luxury vibe!

How to Dress Like Old Money

1. Two Piece Set

If you want something chic that you can easily put together to give you the old-money vibe that you are going for, I recommend this two-piece set!

This set, with its matching top and bottom, is the perfect starter pack for anyone looking to give their closet a luxe makeover.

What’s to love about this set? It’s a no-brainer route to rocking an old-money look without the hassle of mixing and matching different pieces.

2. Tweed Blazer

When hunting for that classic, old-money vibe, don’t sleep on tweed pieces! Tweed is a staple of the old-money aesthetic and one of the easiest ways to get the old-money look.

For example, you might be interested in this tweed blazer! This blazer comes in an adorable pink and grey print that you will love.

Plus, slotting a blazer into your wardrobe lineup is a game-changer, giving you that go-to jacket option that vibes with pretty much any look.

3. Button Up Knit Top

If you are looking for something simple that you can wear every day for the old-money look, I definitely recommend checking out this button-up knit top!

This top is the perfect blend of laid-back and luxe to elevate your daily outfits. Plus, this knit top is all about keeping it comfy while looking effortlessly stylish.

4. Midi Dress

If you love wearing dresses, you might also be looking for a dress that you can wear that goes with the old-money type of look.

If so, I recommend checking out this midi dress. This midi dress comes with puffy sleeves and a subtle, understated design that will definitely give you the old-money type of style.

5. Collarless Tweed Jacket

Another very common style of jacket that you can add to your outfits to achieve the old-money look is a tweed jacket like this one!

This is a tweed navy collarless jacket with stunning gold buttons for a polished vibe. Toss it on over pretty much anything to instantly amp up your outfit with an old-money vibe.

6. Pleated Shorts

Something simple and cute that you can add to your closet for an old-money look is a pair of pleated shorts.

These shorts come in an adorable light blue shade that will look great when paired with a blouse or button-up shirt.

Also, these shorts can be worn for more casual occasions, or you can dress them up with a nice blouse and heels!

7. Sneakers

If you want some basic shoes to add to your old money wardrobe, I recommend finding clean, neutral sneakers with minimal logos and detailing.

For example, these sneakers you could totally pair with your everyday outfits to give you more of a sophisticated look for running errands.

They look super polished and elevated, yet also perfectly comfy and casual.

8. Sleeveless Tweed Mini Dress

For those of us looking for a super cute dress to wear for chic events, I recommend this adorable sleeveless tweed mini dress!

This dress is chic and simple and will be the perfect addition to your spring wardrobe this year. It would look amazing with a cardigan draped over your shoulders and some cap-toe heels.

9. Cable Knit Chunky Vest

Another common old-money clothing item I recommend adding to your wardrobe is a cable knit chunky vest.

Vests are the go-to for anyone aiming to nail that chic vibe. Next time you’re looking for a piece to upgrade your wardrobe, think about snagging a cute vest like this one.

What’s cool about this vest is its versatility – wear it solo or layer it over a basic tee or long sleeve to round out your look!

10. Button Up Maxi Dress

You might also be searching for a maxi dress that goes along with the old-money type of style! If so, I recommend checking out this button-up maxi dress.

Button-up pieces are key for that old-money aesthetic, especially when added to a chic dress like this one, which features a collar and puffy sleeves.

Also, this dress features an adorable yet subtle animal print that you’re going to love.

11. Collared Shirt

Button-up shirts are a staple of classic wardrobes and the old-money aesthetic.

So you can grab your favorite button-up shirt to wear with your everyday outfits, or you can be a little extra and wear a fun button-up shirt like this one!

This button-up shirt has tiny bows on the front to make it extra preppy and polished.

12. Pleated Tennis Skort

Tennis is considered a large part of the “old money” lifestyle, so naturally, a tennis skirt will help you get an old-money look.

For example, this pleated tennis skort will add something girly to your looks while also giving you an old-money vibe.

Just pair this skort with a cute polo or button-up shirt, and you will have the perfect girly outfit.

13. Contrast Cardigan

Cardigans are also very popular when putting together old-money looks!

For example, this adorable contrast cardigan will be the perfect item to add to your looks that you want to make look more sophisticated.

Contrast designs, as featured on this cute cream and black cardigan, are also a very popular trend when going for the old-money vibes.

And you can’t go wrong with neutral tones in your old-money wardrobe!

14. Loafers

If you are looking for shoes to wear to fancier events, you might want to consider purchasing loafers!

Loafers are the perfect shoe to add to your outfits to give you more of an old money vibe and make you look more chic and sophisticated.

For more on loafers, see our guide to The Best Old-Money Shoes.

15. Pleated Pants

Pants are also a great addition to your wardrobe to achieve an old-money vibe, especially if they are pleated pants like these.

Pleated pants, when added to a look with a button-up top or blouse, will give you an old-money type of look.

Also, what I love about pleated pants like these is you can dress them up by wearing some fancy shoes like heels to make your outfit stand out even more.

16. Sweater Dress

Another type of dress that you might be interested in when trying to achieve the old-money look is this sweater dress!

This dress might be just what you need to add to your wardrobe for a comfy dress that will also give you a more sophisticated and chic vibe.

I’m also obsessed with the adorable bow this dress has around the collar!

17. Short Sleeve Textured Knit Tee

Knit designs and materials are a big deal for channeling that old-money look.

If you’re on the lookout for something that nails this vibe, definitely consider this short-sleeved textured knit tee. It’s the perfect addition for anyone aiming to keep it simple yet sophisticated.

18. Wrap Knit Top

Another knit clothing item for fancier outfits is this off-shoulder wrap knit top!

This top comes in a gorgeous cream shade and features a wrap design that has both relaxed and polished vibes.

What I love about this top is you can wear it with more casual clothing items like jeans, or you can dress it up a bit and wear it with a skirt.

19. Tweed Cardigan

If you are looking for a cardigan to add to your outfits but want something a bit more oversized than the last cardigan I listed, I recommend going for this tweed cardigan!

This cardigan will not only give you something super comfy that you can wear with everyday outfits, but it will also give your looks more of the sophisticated vibe that you are trying to achieve.

20. Linen Jumpsuit

A linen jumpsuit like this one is quintessential old-money summer chic.

I love wearing jumpsuits because they make putting together an everyday outfit so much easier, so if you have been looking for the perfect outfit to revamp your wardrobe, this might be it.

What I also love about this linen jumpsuit is if you are going somewhere more fancy, you can dress it up with cute heels!

21. Ballet Flats

Looking for shoes that’ll give your everyday fits a polished touch? You need these ballet flats.

These flats are simple, but they pack a punch in making your day-to-day outfits feel more refined and put-together. Plus, they’re old-money aesthetic-approved.

22. Round-Toe Chunky Heels

For fancier events, you might also be looking for a cute pair of heels you can add to your old-money looks!

If so, I would recommend checking out a cap-toe pump. Cap-toe heels are the perfect shoes to add to your wardrobe if you are trying to go for a more chic and sophisticated vibe.

These heels come in a super cute black and cream combination that will look adorable when added to your old-money-style outfits!

What items from this list are you going to add to your wardrobe?

What clothing items do you think give off old-money vibes? What kind of old-money outfits do you like to wear?

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