Ready to Look Expensive?
Adopt the secrets of the wealthy-, expensive- and gorgeous-looking women.
Congratulations!
You are on the right track to becoming the woman you always wanted to be!
52 Old Money Preppy Style Outfits That Will Make You Look Old Money
In this blog article, we’re going to show you the best Old Money Preppy Style outfits that will make you look expensive.
These are the exact outfits the rich swear by and that will make you look so too.
Table of Contents
52 Old Money Preppy Style Outfits That Will Make You Look Old Money
1. Button-Down Shirt + Pullover Over Shoulders
2. Tweed Jacket + Black Tights
3. Old Money Aesthetic Outfits: Tennis Skirt + Polo Shirt
4. Wool Coat + Knee-High Boots
5. Old Money Aesthetic Outfits: Cream Jeans + Basic Top
6. Tweed Jumpsuit + Pink Coat
7. Knitted Turtleneck Pullover + White Suit Pants
8. Jeans + Blouse
9. Black Blazer + Knee-High Boots
10. Tweed Dress + Black Tights
11. Blazer + Skirt
12. Knitted Top + Black Mini Skirt
13. Oversized Knitted Sweater
14. Oversized Sweater + Silk Dress
15. Black Shorts + White Knitted Sweater
16. Tennis Skirt + Sweater Vest
17. Tulle Dress
18. Oversized Button-Down Shirt
19. Knitted Suit
20. White Poplin Dress
21. Pastel Yellow Dress
22. Jogging Suit
23. Tennis Skirt + Button Down Shirt
24. Pink Plaid Tweed Blazer + White Dress
25. White Shorts + White Knee-High Boots
26. Tweed Dress Suit
27. Cropped Blazer + Black Shorts
29. Knitted Dress
30. Knitted Button-Down Sweater-Dress
31. Blouse + Leather Skirt
32. Silk Dress
33. Black Tennis Skirt + Button-Down Top
34. Plaid Dress
35. White Dress + Sweater Vest
36. Oversized Black Blazer + Knitted Sweater over Shoulders
37. Silk Dress
39. Oversized Black Blazer + Black Tennis Skirt
40. Black Mini Dress
41. Knitted Top + Black Skirt + Mary Jane Pumps
42. Knitted Top + Cream Jeans
43. Plaid Sweater + Black Shorts
44. Pastel Yellow Dress + White Gloves
45. Black Midi Dress
46. Black Dress + White Button-Down Shirt Underneath
47. Black Tennis Skirt + Knitted Pullover
49. White Tweed Suit
50. Faux Fur Cream Top + Straight Leg Creme Jeans
51. Cropped Oversized Blazer + Yellow Denim Skirt
52. Black Mini Dress + Hat
What is the Old Money Aesthetic?
The “Old Money Aesthetic“ refers to the nobility, the aristocracy, or the rich upper class in general. These are people who haven’t earned their wealth themselves but have inherited it.
A motif of this aesthetic that can hardly be overlooked is the sports of golf and tennis, which in most countries tend to be associated with the upper class. Polo or other equestrian sports are also seen time and again.
By stamping these motifs, you can see that it’s a timeless, very classically chic style that exudes pure elegance and therefore enjoys great admiration in society.
And contrary to what you may think, the enthusiasm for this aesthetic can be observed in all generations and even in the youngest fashion fans.
Because in truth, the hashtag #oldmoneyaesthetic has more than 90 million views on TikTok worldwide, while #oldmoney already counts 322 million.
So the trend is clear: fashion-wise, we’re moving – finally – back towards timeless fashion. Fashion houses like Chanel and co. will surely be happy about that!
How to Dress Like Old Money?
To recreate the old money style, it is first important to understand the basic rules of this aesthetic, so that you can do it with ease.
These are the main tips you need to follow to look old-money:
1. Light Colors
Especially in summer, a simple and super helpful tip is to go for lighter colors like white, light blue, pink, yellow, or other light pastel shades.
This is because the rich know that light colors not only protect them from excessive sunlight, but these colors also make them look much neater, friendlier, and most importantly, chicer.
Dark clothing quickly looks dull and can leave a rude, distant impression, which is to be avoided at all costs, especially for rich people.
After all, just because these families are already wealthy doesn’t mean they don’t want to expand their wealth. And for that, good contacts and long business relationships are essential – so their overly bright clothing sets a foundation stone for friendly, open conversations here.
So if you’re also interested in networking with successful, interesting personalities, you should heed this simple but effective tip.
2. High-Quality Fabrics
Bad materials can ruin your outfit within seconds. Because even if you think that most people don’t see the fabric composition of your look: They do, unfortunately.
Maybe not necessarily the direct fabric mix, but still, you see – and worst case you smell – the bad production and manufacturing of these items.
Pieces from predominantly synthetic fabrics should be taboo from now on! They only make you sweat excessively anyway, always look cheap, and make you look anything but elegant.
I, therefore, recommend, especially if you’re on a budget, that you create capsule wardrobes with 20-30 elegant, timeless pieces for each season, which you can then combine in the most diverse chic ways. This will not only save you a lot of time and stress, but also a lot of money.
So invest rather in a few, high-quality materials, for example, linen, cotton, wool, silk, or cashmere instead of unnecessarily many pieces in poor quality at the worst of almost fashion stores to own.
3. Tie a Sweater Over Your Shoulders
Who doesn’t know this preppy, adorable look?
I actually put together a few outfits in this style myself yesterday and even though I already loved tying sweaters over my shoulders before, yesterday I realized even more how much it makes the outfit more elegant.
And I highly recommend this to you too: tying a sweater over your shoulders has such a great, casually elegant vibe that puts you right into that “right off the tennis court” flair.
It’s basically such a simple trick, but it really works wonders and is practical too. When it gets a little chilly in the evening, you’ll have something you can throw on right away and you won’t have to lug a jacket around.
4. No Flashy Designer Brands
Something that wealthy, “old money” people probably hate the most are flashy logos that literally scream “I want to look rich“.
Since these people 1. don’t need it and 2. don’t find it elegant, you won’t see anyone with old money walking around like this.
And that’s a good thing – it gives us the advantage of not having to wear designer pieces to recreate this aesthetic.
With high-quality materials and a good fit, everything is already done – it shouldn’t even be recognizable from the outside, from which brand an item is. And if you can see a logo it should be a small, minimalist logo such as on Ralph Lauren* or Lacoste Polos*.
5. Tennis Clothes like Tennis Skirts or Polo Shirts
An important motif of the aesthetic is the sporty chic side of golfing, playing tennis, or polo.
That is why many wear the elegant style as in these sports.
The obligatory “hanging sweaters over shoulders” actually comes from golfers, who would otherwise be too cold. This style always has something very elegant, and casual.
The good thing about it: To look old-money, you can also be sporty and elegant on the road. The best way to do this is with an elegant tennis skirt or a polo shirt. But never forget the sweater over your shoulders 😉
How Do You Dress Old Money on a Budget?
If you aspire to look like a member of the old money crowd, dressing on a budget may be a challenge. Cashmere sweaters, tailored suits, and other high-end clothes aren’t cheap. If you don’t have a lot of money to spend, don’t despair! We’ve got some tips for how you can dress like old money even if you’re on a budget.
How Do I Get An Old Money Aesthetic?
Since there is more to the “old money aesthetic” than just dressing accordingly, I recommend you to become more and more the best version of yourself on your journey to be able to live this lifestyle in the long run.
This means, for example, visiting places where old money people hang out to get inspired by them or maybe even connect with them. These can be fancy restaurants, golf courses, or even tennis courts. You might even attend a polo match near you. The main thing is that you’re surrounded by people who inspire you in this regard.
In addition, you won’t get distracted so quickly and you’ll be able to integrate more and more of the other themes that old money people deal with as well, to integrate these aesthetics not only into your clothing style but also into your lifestyle.
Where Did the Old Money Aesthetic Come From?
As I mentioned earlier, so-called “old money” is money that has been passed down and inherited over several generations.
Moreover, families with old money don’t come from middle-class or working-class families, but from businesses or fortunes from several generations ago.
The so-called “new money,” on the other hand, was earned recently. The new rich are first-generation millionaires and billionaires.
Accordingly, the “Old Money Aesthetic” originally came from families with aristocratic titles (titles of nobility) in Europe or also from the WASP culture (White Anglo-Saxon Protestant) in the United States, who can afford, for example, the sports of polo, golf or tennis.
In series like “Bridgerton” or “The Crown,” we see again and again such families, who with their elegant, chic style contribute to this style (again) gaining popularity.
What Are the Characteristics of the Old Money Style?
- Bright colors like white, light blue, or rose
- High-quality fabrics like linen, cotton, silk, wool
- The stereotypical tying of the sweater around the shoulders
- Tennis clothes like tennis skirts or polo shirts
- No flashy designer logos
- Hats, silk scarves, and gloves are often-used elegant accessories
What Are Old Money Style Brands?
The old money brands that best reflect style are Chanel, Loro Piana, Ralph Lauren*, Barbour, Ermenegildo Zegna, Brunello Cucinelli, Brioni, and Armani.
In particular, Brunello Cucinelli and Hermès are known for their timeless, elegant designs and quality craftsmanship, as well as their heritage for old money clothing.
Other brands such as Louis Vuitton, Gucci, Balmain, and Prada, however, have more of a new-money vibe due to their flashy logos and oversized fits.
14 Affordable Old Money Brands
12 Storeez
Taking inspiration from women’s lives and needs, 12 Storeez strives to create a wardrobe that you will wear for years to come.
A capsule wardrobe for a busy life. Clothes that work for you time and time again. Timeless, feminine, and subtle.
We earn a commission if you make a purchase, at no additional cost to you.
Arket
ARKET is a modern marketplace and a trendy lifestyle destination at the same time: they offer high-quality products for men, women, children, and living spaces.
The name ARKET is a reference to the Nordic heritage and our Nordic soul and means "sheet of paper" in Swedish.
It symbolizes creativity and innovation and open-mindedness in connection with the simple aesthetic that runs strictly through their range.
We earn a commission if you make a purchase, at no additional cost to you.
Massimo Dutti
Massimo Dutti, part of the Inditex Group, is the higher-quality, more expensive brand next to Zara.
We earn a commission if you make a purchase, at no additional cost to you.
My Personal Favorite
Karl Lagerfeld
Behind the dark sunglasses, elegant suit, and immaculately styled hair - behind the appearance of the global fashion icon - Karl Lagerfeld was above all one thing: an incredible human being.
Blessed with an extraordinary capacity for perception.
Incredibly well-read. A fantastic storyteller. His friends knew him as a brilliant, generous, and loving person. And what may surprise many: as someone who had a sharp sense of humor and always used it at just the right moment - a quality that made him an incredibly entertaining conversationalist.
So behind the carefully staged image that the public saw of him, there was an incredible amount more...
We earn a commission if you make a purchase, at no additional cost to you.
& Other Stories
Designed in Paris, Stockholm, and Los Angeles - for stylish diversity.
Each piece of the design studio has its unique expression, reflecting the constantly evolving, characteristic styles of the city in which it is located.
We earn a commission if you make a purchase, at no additional cost to you.
14 Old Money Designer Brands:
What Is New vs Old Money?
The so-called “old money” refers exclusively to inherited wealth that wasn’t generated by families in the working or middle class, but by families in the upper class, or rather the aristocracy. This is wealth that has lasted for several generations.
In the case of so-called “new money,” it is the exact opposite: here, “new money” refers to the wealth acquired by or in the first generation.
Examples of new money include many prominent corporate CEOs, musicians, entrepreneurs, famous athletes, and social media influencers.
How Can I Look Expensive? – 7 Simple Tips
These are 7 simple tips that really anyone can follow and look a lot richer and more attractive!
- Cashmere is your best friend
- Wear more navy blue than black
- Invest in a glamorous little black dress (and don’t just wear it to funerals)
- Let your everyday jewelry be a big statement
- Carry a clutch purse that’s smaller than you think you need
- For evening, definitely go sparkly and sheer, but keep it classy and elegant, not racy or low-cut.
- Stick with classic, timeless cuts instead of trendy ones
Takeaway: These tips will help make you look wealthy!
Do Wealthy People Buy Luxury Brands at all?
That’s a challenging question, which we can only answer very stereotypically again.
It’s clear that wealthier people, in particular, also buy from more expensive brands. But just because a person wears a designer brand, it doesn’t mean they are affluent. There are far too many good tricks for faking wealth these days.
But I can say from experience: the really wealthy people hardly ever wear clothes where you can immediately recognize the brand. In most rich circles of acquaintances, it is simply indecent, if not inappropriate, to wear clothes with a thick inscription or an all-over print with a designer logo.
They are much more likely to go for genuine quality in the form of proper material, cut, and durability. But in the end, most of them don’t care about the brand – it’s just that quality often comes at a price, and that’s why wealthy people tend to spend more on their clothes.
Of course, there are also just as many people who wear these “flashy” clothes who have money, but usually, these are then rather nouveau riche than really rich.
How Can I Make My Face Look Rich?
The rule here is quite clear: less is more! Full-face makeup not only hides your true beauty, but it also looks super unnatural – and just not luxurious!
Being a high-class woman also means knowing your value and accepting yourself. Sure, it’s hard to always feel comfortable in your skin, but it’s about not having to pretend or put on a mask.
Only when you accept yourself as the fabulous woman you are and love yourself (to come back to the topic of charisma ;)), you start to shine from the inside and outside. Charisma comes to 99.9% of your inner beauty and how you perceive yourself.
So dare to feel comfortable in your skin, and you will notice what great things you suddenly attract.
How Can You Tell if a Woman is Old-Money (+ How Does She Behave)? – 20 Unmistakable Signs
Finding out whether a woman is a wealthy or old money isn’t so easy these days.
Because nowadays you can not only buy a driver’s license or a high school diploma and fake it, but also the status of being “rich”.
In truth, it’s often the other way around: the really rich are usually less conspicuous and also often very restrained, relying on timeless, minimalist pieces.
Those who are forced to look rich often tend to want to show very obviously what they have:
This can be through (fake) watches or other designer pieces that very obviously show the brand’s logo.
Nevertheless, there are less obvious signs that tell you that a woman is old-money and wealthy:
- Well-groomed hands
- Manicure and pedicure (not too long nails, well-groomed!)
- Natural make-up or none at all (NO full-face make-up!!)
- Shiny, voluminous hair
- Fresh scent (not too heavy perfume!)
- Never without a little souvenir when you are invited
- Better overdressed than underdressed
- Decent jewelry (don’t overdo it!)
- The colors of the outfit match your complexion & hair color
- Shaved
- Well-groomed (no bad breath, no smell of sweat!)
- A valuable watch
- She takes care of her figure (healthy diet, sports!)
- She does not drink much alcohol
- Natural tan (no solarium or self-tanner!)
- She is friendly and smiles a lot
How to Dress Old Money in Summer?
Summer is the season where you can really show off how to dress like old money.
It’s the season where you can show off all the great pieces that you’ve been saving for the cooler months.
However, summer temperatures can make some of our favorite old money staples too hot to wear.
So, what do you wear for old money in the summer? Here are some tips.
Wear Lighter Fabrics
You don’t want to be too hot, and you don’t want to sweat too much, so you should wear lighter fabrics in the summer. This includes your pants, blazer, and shirt.
Wear Looser Clothes
Tighter clothes restrict airflow and make you hotter.
Looser clothes, like slacks and a pair of chinos, will let your body breathe and keep you cooler.
Wear Lighter Colors
Darker colors aren’t always too hot.
However, lighter colors tend to be more comfortable in the summer.
Wear lighter colors in the evening and darker ones during the day
If you’re worried about being too warm in the middle of the day, you can always pop on a pair of sunglasses or a hat, or wear a lighter color in the daytime.
How Do Old Money People Act?
You can’t just dress like you have money, you have to act like you have money too.
Old money people are polished, well-spoken, and always know the right thing to do.
If you aspire to be like this group of people, act like you have money!
Here are some tips for how to act like old money.
Be Well-Dressed at all Times
This is one of the most important things. If you don’t look like you belong in high society, you won’t be invited in.
Be Polite
Polite conversation, even with people you don’t know well, is a must. You should also be polite when you give your opinion, even if you think it’s the right one.
Be Well-Spoken
Make sure you don’t mumble, speak too quickly, or stutter. When you speak, sound confident and well-spoken.
Have Class
When you act like old money, you want to exude class. This means being dignified, having a sense of humor, and staying away from drama.
What You Should Do Now:
There are a lot of tips and tricks when it comes to dressing like old money.
The best way to get there is to simply buy quality pieces that will last a long time. When you buy high-quality clothes, they will last for years and will never go out of style. So, if you have the budget, that’s the best way to go. And if you don’t, don’t worry! With a few simple tips, you can dress like old money no matter what your budget is.
*Disclosure about the article: “How to Dress Like Old Money Woman“: We only recommend products we would use ourselves and all opinions expressed here are our own. This post may contain affiliate links that we may earn a small commission at no additional cost to you.
If you liked this blog article about the article: “52 Old Money Preppy Style Outfits That Will Make You Look Old Money”, don’t forget to follow us on Pinterest so you don’t miss any more fashion and beauty news!
