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When I hear old money outfits, I think of elegance, sophistication, and quiet luxury.
Think Audrey Hepburn in Breakfast at Tifanny’s.
Think Marilyn Monroe in Gentlemen Prefer Blondes.
No shade to new money, but old money outfits know how to make a statement without being unnecessarily loud and tacky.
While the old money aesthetic seems to be taking the internet by a storm and everyone seems to be obsessed with it.
We cannot ignore the fact that, without the right guidance, you might end up thinking it’s either boring or hard to pull off— especially if you’re just starting out.
So, if you are looking to take your wardrobe game to the next level and look rich ( even though we’ve got student loans breathing down our necks) then you are in the right place.
Let’s just call it a form of manifestation.
You know what they say “ delulu is the solulu”.
Today, I have created a list of 27 old money outfits that will have you looking like you came from generational wealth.
These are pieces that you can wear to a country club and instantly turn heads.
The kind that will have millionaires and billionaires ready to marry you in Lake Como, fly you out on private jets, and sail with you on classic yachts.
So, get ready, besties.
It’s about to be about to be Coco Chanel meets Old Hollywood in here.
1. Blazer + Skort + Bag
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Blazer // Skort // Bag // Sunglasses // Shoes
A tailored blazer and mini skort is an old money outfit that effortlessly blends modern luxury and timeless sophistication.
Not only is this ensemble stylish, but it is also very feminine.
Moreover, it’s a versatile look that can seamlessly transition from office to after-hours cocktail.
Add a pair of sunglasses and a matching white handbag for a polished, put-together finish.
2. Blazer + Shirt + Tights
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When it comes to old money outfits, we cannot do without a blazer— so yeah you will definitely be seeing a lot of them on this list.
But let’s get into this look for a minute.
A classic blazer paired with a white button-down shirt and sheer tights creates a sophisticated ensemble with a touch of feminine flair.
This ensemble is more than just classy— it also whispers “expensive taste”.
3. Halterneck Dress + Scarf
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Dress // Sunglasses // Scarf // Shoes
The first thing that came to my mind when I first came across this look is– “ A billionaire wife or daughter going on a shopping spree with an AMEX Black Card.
That’s the vibe I’m getting from this look.
This is not just old money— it’s old money deluxe.
Honestly, I’m struggling to find the words that do justice to the aura and glam this look gives off.
Although this outfit shows skin, it doesn’t do it in a way that it appear vulgar.
Instead, it’s delicate, refined, and effortlessly elegant.
Pair a stunning halter neck gown with crisp white heels.
Then elevate the ensemble with a chic handbag and sunglasses.
Finally, for that princess touch, wear your hair in a half-up hairstyle with tendrils on both sides.
I recommend adding a scarf to the look just as seen— it’s so pretty and girly.
4. Maxi Dress + Hat
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Dress // Hat // Sunglasses
One thing I absolutely love about old money style is how you don’t really need to do too much to make a bold fashion statement.
In my opinion, such outfits often outshine someone wearing labeled designers from head to toe.
That’s the thing about old money outfits that literally blows my mind.
Take a look at this gorgeousness we have here for example.
A simple maxi dress paired with a striped hat, chic dark sunglasses, and minimal jewelry — A look for days.
It’s understated, timeless, and still giving luxury– I love, I like.
Moreover, it is the perfect vacation outfit —- so be sure add it to your 2025 summer vacation outfits list.
5. Tank Top + Shorts + Sweater
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Top // Shorts // Bag // Belt // Sweater
Old money summer outfits are some of my favorite pieces to wear because they are the definition of polished sophistication.
Just like this look here– an epitome of old money style with a modern twist.
If this is something you want to rock, pair a white tank top with tailored shorts and a sleek belt.
Now here’s the fun part.
Instead of wearing your sweater, just drape it over your shoulder and tie it to the front for that elevated touch.
Don’t forget your sunglasses and handbags, too, babes.
They are the VIPs of this ensemble, bringing the whole look together.
Speaking off summer, check out this stunning summer outfit ideas to slay this season like never before.
6. Off Shoulder Top + Skirt + Sweater
Credit: sophielousiesdiary
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Top // Skirt // Belt // Sweater // Sunglasses
Old money aesthetic without monochrome outfits?
I heard it only exists in Neverland.
Start by rocking an off-shoulder top in white, combined with a pleated maxi skirt.
Of course, don’t forget your sunglasses (at this point you already know the drill).
Next, throw on a belt and drape your sweater over your shoulders —because we are trying to be the next Anna Wintour.
Perfect for brunch, boat cruise, and after-hours cocktails.
We stan a versatile queen who knows how to serve anywhere.
7. White Vest + Maxi Skirt
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Top // Skirt // Sunglasses
This is exactly what I mean when I say old money outfits aren’t over the top yet they will always SERVE!
For this look, opt for an all-white outfit— because white shows refinement and grace.
8. Tweed Dress + Sunglasses
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Dress // Sunglasses
Tweed dresses are a staple when it comes to old money summer outfits.
Not only are they classy, but they also bring youthful charm that’s impossible to ignore.
If you are starting out in dressing like old money, a tweed dress is a good place to start.
This look is perfect for dinner dates, country clubs, brunch, and casual gatherings— depending on how you style them.
Add a pair of dark sunglasses and a handbag to complete the outfit.
9. Long Jacket + Pants + Shoes
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One word for this look — Regal.
This ensemble is giving the CEO of a billion-dollar company.
If you are looking to embrace the old money style for the office, then this look should be at the top of your list.
But you might get mistaken for the CEO by your fellow co-workers or even your boss.
And probably win an award for “Best Dressed Employee of the year”.
10. Off Shoulder Maxi Dress + Bag
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So feminine, so delicate—like a dandelion—and outstandingly beautiful.
This dress is a perfect choice for both garden parties and dinner parties.
I’m obsessed with how it delicately highlights the shoulders while offering a flattering fit that gently hugs the curves, creating a graceful silhouette.
Moreover, with this type of old money outfit, less is actually more.
You don’t need to go crazy with accessories or elaborate styling—let the dress be the main character.
All you need are a pair of simple stud earrings and a sleek black handbag—and that’s it.
11. Blazer + Flared Skirt
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Blazer // Skirt // Shoes // Bag // Sunglasses
Now this is what we call Timeless European elegance.
A classic combination of Blazers and midi skirts remains one of the best old money outfits for professional settings.
In fact, anything that features a blazer tends to look refined and polished– making it a must-have when transitioning into the old money style.
To finish the ensemble with finesse, opt for sleek sunglasses, white shoes (preferably heels), and a statement shoulder bag that adds just the right amount of contemporary edge.
12. Button Down Shirt + Wide Leg Pants
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Shirt // Pants // Belt // Bag // Shoes
Every post I come across about old money style always has a button-down shirt and wide-leg pants on the list.
So you know it’s a classic.
It is simple, easy to put together but very clean and sophisticated.
Also, its the perfect business casual outfit for office, professional meetings and co-operate events.
13. Trench Coat + Blazer + Pants
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Coat // Blazer // Pants // Boots
THIS is top-tier fashion— nothing but iconic.
It’s giving boss lady vibes.
From the long trench coat to the tailored blazer and the suit pants.
Every piece comes together to create this perfection we have here.
14. Mini Bubble Dress + Jacket
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The mini bubble dress and tweed jacket create a sleek and stunning old money outfit that whispers “quiet luxury”.
Accessorize with minimal jewelry– after all, we don’t want to overwhelm the look.
15. Vest + Pants + Handbag
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Top // Pants // Bag // Sunglasses
For a casual and simple old money outfit, start by pairing a plain white vest with wide-leg pants.
Then, complete the look with a structured bag and chic sunglasses.
By the way, am I the only one who feels this is way more than just a casual outfit?
I mean, I’d wear this to brunch, after-hours cocktails, even events.
It’s simple, yes– but glamorous at the same time.
16. Off-Shoulder Dress + Fascinator
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Dress // Belt // Fascinator // Bag // Shoes
Just when I thought I had found my favorite old money outfit, along came this– now I’m torn.
There’s nothing more timeless than an off-shoulder pleated midi dress combined with fascinator.
This elegant ensemble is perfect for casual events, afternoon tea, and date nights.
It oozes glamour with a refined, understated charm.
Moreover, it works seamlessly as both a summer and winter old money outfit.
For winter, simply layer it with a trench coat for added warmth.
17. Top + Mini Skirt +Shoulder Bag
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Oftentimes, I hear people say that you can’t show skin and still embody the old money aesthetic—— because it somehow defeats the sense of class.
But that’s absolutely false.
Showing a bit of skin, especially your legs, can be incredibly elegant when done tastefully.
In fact, there’s such a thing as sexy old money outfits— and the look above is a perfect example.
And does it look tacky? Absolutely not!
Oh if you have a girls’ night out coming up soon, don’t sleep on this outfit.
18. Polo Shirt + Wide Leg Pants + Slingback Heels
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Make a statement with a polo shirt and wide-leg pants.
Add a handbag, sunglasses, and a pair of slingback heels for that elevated touch.
19. Blazer + Wrap Scarf + Mini Skirt
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Jacket // Skirt // Tights // Scarf // Top // Sunglasses
Another feminine choice for summer 2025, this outfit goes perfectly with oversized sunglasses and a wrap scarf.
The wrap scarf and sheer tights took the look from 100 to 1000!
20. Top + Satin Skirt
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The satin skirt brings a relaxed vibe to the crisp white top.
All you need to make this look pop is a pair of white heels and a little bag.
21. White Maxi Dress + Shoulder Bag
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It’s the dress for me.
So mesmerizing— It owns the spotlight and doesn’t need anything extra to shine.
Well, maybe a cute little bag for your lip gloss.
22. Halterneck Top + White Shorts
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Opt for a matching halterneck top and shorts to create a fresh and sophisticated look.
For that flawless finish, you need a white handbag and matching sandals.
Altogether, this ensemble is a definition of clean, polished, and classy.
Ideal for going for afternoon tea, to the art gallery, and to yacht parties.
23. White Vest + Black Maxi Skirt
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Top // Skirt // Sunglasses
This is a fashionable and polished way to show up for office meetings and professional seminars.
A white vest brings a sharp, structured feel while the black maxi skirt adds elegance and flow to the look.
To elevate the look, throw on some oversized sunglasses for that edge, and a cute handbag pulls everything together.
24. Tank Top + White Maxi Skirt + Belt
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Top // Skirt // Shoes // Sunglasses
For this look, you really want to go light-handed with the accessories.
I think that’s the thing with old money outfits.
The outfit does most of the work and brings all the glam.
Therefore, all you have to do is add minimal tasteful accessories and you’re all set to look like a million bucks.
25. Striped Button-Shirt + White Shorts
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Shirt // Shorts // Sandals // Bag
The relaxed and oversized shirts offer comfort, while the white shorts create a clean look, resulting in a prim and proper outfit.
Overall, this outfit strikes a balance between formal and casual, depending on the occasion.
For instance, in a professional setting, you can switch the shorts for white pants to maintain a co-operate friendly look.
Moreover, these clean pieces make this outfit great for spring and summer.
Especially when paired with sandals or white heels, again depending on the occasion.
Additionally, the handbag adds a feminine touch to the ensemble.
And of course, your favorite outfit elevator—sunglasses—ties everything together.
26. Halterneck Top + Skirt + Black Belt
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So here, we have a halterneck top with a draped plunging neckline, paired with a white maxi skirt featuring a high slit.
Not only is this old money outfit stylish, but it’s also hyper-feminine—exuding elegance and confidence.
27. Romper + Hat + white Heels
Credit: jarinpat
This is the queen of all old money outfits on this list.
Now tell me if this ensemble doesn’t look like generational wealth?
The aura of this look is simply unmatched— It’s giving femme fatale.
From the romper to the hat, and from the shoes to the bag, everything comes together to create this elegant, sexy, and highly sophisticated ensemble we have here.
Remember how I mentioned torn between which look was my favorite? Well, that’s no longer the case.
This is officially my favorite old money outfit of 2025.
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Sadly, we’ve come to the end of this article.
Whew! What a glamorous ride it’s been.
Each outfit just kept raising the bar– honestly, I was floored!
Now you no longer have to feel confused about how to dress like old money or where to buy old money clothes.
Hopefully, this article has shifted your perspective and shown you that old money outfits are anything but boring.
So, what was your favorite? Let me know in the comments.
And if you are torn about which one to choose— trust me, I get it.
Every single outfit is a hit.
My advice? Just go ahead and choose them all.
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