The old money aesthetic is timeless and preppy at the same time. It brings to mind private school in the fall, and maybe a bit of East Coast sailing style in the summer. It is timeless without looking old-fashioned or overly mature.
It feels bold enough because of how sleek it is in color and in fit. The pieces that you have in an old money wardrobe are flattering and high quality, so they look chic in a wide variety of settings. Here are some ways to achieve this aesthetic.
1. Cream Cable Knit Sweater with Ivory Trousers
A classic way to look chic and old money while still timeless is a high quality knit sweater. A knit is never going out of style, and a cable knit especially is something that’s sometimes passed down because of how long lasting they are. Even more points if it’s in a luxury material, like cashmere.
A cream is a good solid that goes with various color pairings. Ivory trousers with cream are good neutrals. There’s nothing popping here, except that together, the outfit does pop.
We often see the old money aesthetic coinciding with French girl style and the clean girl aesthetic. They all have a few things in common. Crisp white t-shirts are inherently comfortable, but there’s something about a clean, crisp white t-shirt that’s a classic and isn’t going anywhere.
Navy and white together are a timeless color combination. Straight jeans feel more timeless than wide leg jeans or skinny jeans. Ballet flats add a little bit of femininity to counteract the more structured blazer.
3. Camel Coat with Black Turtleneck and Black Trousers
There’s nothing more timeless than camel with an all black base. A black turtleneck is one of the first pieces I would grab for an old money chic outfit in a hurry. Black on black looks so glamorous and still subtle.
She can wear the loafers here, she could wear boots, or she could wear riding boots if she really wanted to lean into the preppiness. I think the subtlety of the black and brown color combination can still be played up with more color, maybe in the shoes and the accessories.
4. White Button-Down with Beige Pleated Trousers
This is a little bit more of a workwear look. It definitely feels timeless and old money because of the simplicity, which is working. Rather than an oversized button down, this is a more tailored button down that’s tucked into her pleated pants.
Both of these items fit her perfectly. They may be tailored, and the tuck especially adds a little bit of polish without having to think more about the pieces that you’re using in the outfit.
5. Striped Breton Top with Cream Chinos
This striped Breton top is one of the ways to add pattern without doing too much. The old money aesthetic definitely works with a Breton top. It feels like sailing, it still feels understated, and it feels European, especially when paired with the cream chinos.
Cream pants are a bolder statement move. I like that they’re a chino here rather than a jean. A jean would feel a little bit more summery, maybe vacation, while this chino feels a little bit more upscale, more preppy, and more mature.
Because the pants are a little bit more mature, I like that she has a ballet flat here rather than a loafer. It feels more playful with the ballet flat, and the outfit together is something that I could see myself wearing. If it were a loafer, it might be a little bit too structured, maybe a little bit too masculine for some of us.
6. Cashmere Polo with High-Waisted Trousers
There’s not much going on in this outfit. Color-wise, fit-wise, really everything that it has going for it is in the cashmere.
This is one of the simplest ways to look put together, old money, preppy, and chic: have a high quality item, or hopefully the whole outfit. But even just one very high quality piece will elevate the whole thing by miles.
7. Tweed Jacket with Dark Denim
A tweed jacket is definitely timeless and old money. It has a Chanel look, even if it is not Chanel. Tweed is a mature fabric while still being youthful, usually in the cut.
The neckline here is modest, which is also inherently old money. It’s not trying to prove anything or show off too much. It has a little bit of interest in the buttons and the outline, but other than that, it’s a pretty simple outfit overall.
8. Monochrome Oatmeal Knit Set
The cream, neutral, or oatmeal knit set is one of my favorite old money hacks. It’s one of the few ways to do leisure or lounge wear and still look chic or old money, in my opinion. I wouldn’t say a knit set is timeless, because it actually feels pretty modern. However, it’s very chic.
There are multiple ways to do the top. This is a cardigan as a top. There are also hooded versions and tank versions. I usually like it in a lighter neutral. I think it pops a little bit more than a black would. I haven’t seen many navies, and I would be interested to see that, but maybe a charcoal would also look as chic as a cream.
9. Black Midi Dress with a Camel Cardigan
The black and camel combination is taking another avenue with the cardigan. Usually we see the camel accent on top of the black with a coat, maybe a trench or a wool coat. Here a cardigan adds a little bit of nude, almost, to the outfit. What could otherwise be a lot of black on her looks a little bit less imposing because of the camel.
I like the ballet flats with this midi length dress. Midi is my favorite length of all time. I believe it to be timeless and chic, and I think there’s no situation in which a midi wouldn’t make sense.
10. Linen Blazer with White Jeans
This is such a chic combination. Starting with the white jeans, they’re loose without being baggy, almost fitted, but they still have a little bit of room so they’re not showing every crease or lump. The white tank underneath is almost clean girl, and definitely timeless. It feels crisp while still being casual.
A linen blazer is a good addition for adding polish without adding too much heat. Linen is a high quality, high value fabric that will definitely never go out of style. It genuinely has a use in the summer. It’s a piece that you can keep in your wardrobe for many years, which is an old money practice.
Navy and brown is a very simple color combination. Navy feels very old money, very timeless, and preppy. Navy, burgundy, maroon, and dark rich colors like that pair well with brown leather accessories.
12. Silk Blouse with Wide-Leg Wool Trousers
Again, a wide leg helps to create a flattering silhouette when the top is tucked in. With the top tucked in, the belt gives a little bit more of a cinch at the waist, and then the wide leg does the rest of the work. A wide leg is very flattering, especially with a heel. A heel can mean a pump or a boot. A wide leg can even have a calf length boot underneath it.
Wool is also an old money chic fabric that’s long lasting and high quality.
13. Quilted Jacket with Corduroy Trousers
Quilting rather than a puffer is old money outerwear. A puffer would be more like athletic wear, while quilting is more like hunting and outdoorsy. It’s long lasting, and it traps air within the layers without being an athletic material.
The corduroy in the pants coordinates with the corduroy in the collar. Overall, this is a warm, sturdy outfit that’s good for colder weather while looking chic.
14. Black Crewneck Sweater with Camel Skirt
Again, we have a midi skirt, almost an A-line here. It’s a classic silhouette paired with a crewneck sweater. If she wanted to, she could untuck the crewneck sweater and have a button up popping out. Here she has a longer, calf length boot under the midi skirt. I like high quality leather. This is a simple color palette that reads old money.
If she wanted to, she could pair this with a darker jacket. I wouldn’t necessarily go with a camel jacket in this situation because of the camel skirt. Maybe a lighter color than camel, or a darker colored jacket. She could also put tights on underneath the midi skirt, because nothing will be showing with the boot.
15. Trench Coat with White Shirt and Ankle Trousers
The trench coat is doing its job keeping her dry. It may not be perfectly waterproof, so an umbrella is definitely a good choice. In terms of umbrellas, I actually like the old style that she has here with the hook handle. It definitely feels a little bit more old fashioned than the compact ones. The compact ones are more modern, but this feels like she has no intention of throwing it in her bag.
These shoes are a good option for rainy weather in the fall, maybe even towards the beginning of winter. Leather is somewhat waterproof, and it can be treated, especially if you’re good at taking care of your things. You can wear this out in damp, slightly rainy weather without worrying too much.
16. Cardigan Jacket with Tailored Shorts
Again, we have this almost tweed looking cardigan jacket. It’s interesting that she chose to wear this in what looks like warmer weather. This Chanel-esque cardigan jacket always reads old money. A simple silhouette, a simple pattern. The details are in the buttons and in the lining that she has.
The bottom almost looks like a linen tailored short. With these natural fibers, like the cotton in the cardigan and the linen short, she shouldn’t be too warm. She could have a clean white tank top underneath the cardigan if she wanted to take it off. These sandals are a simple leather design matching the woven market bag, which is definitely also a classic.
17. Gray Turtleneck with White Wide-Leg Jeans
Here we have a gray turtleneck. I have one very similar to this. I’m personally a huge fan of the turtleneck. A black turtleneck is definitely a staple to have in anyone’s closet, I believe, but I find myself reaching for the gray one almost just as often, as well as cream. Gray is kind of in between the cream and the black, so it can go both ways. You can use it like she’s doing in this situation, for more of a warm neutrals outfit.
The white wide leg jeans are truly a bright white, which helps bring in the coolness of the gray combined with the more taupe long wool jacket. I do like long wool jackets like this when they have a tie belt. There’s something about it that feels a little bit cozier than buttons. It feels almost like you’re a middle-aged rich mom getting up at her vacation house and throwing on a huge cozy cardigan. The tie really changes the feel of the otherwise structured jacket.
I like the suede shoes here. I could also see a darker boot or a darker shoe in general, or maybe something lighter, something that blends into the pant a little bit more, rather than popping out. It does coordinate with the jacket, but it could either pop a little more or blend a little more.
18. Plaid Blazer with Cream Knit and Brown Trousers
Again, we have a plaid blazer. This definitely reads old money, preppy, and timeless. It feels like Ralph Lauren. It feels like the countryside, maybe in a European way. I like the trousers with the loafers. That’s a classic silhouette.
Overall, this silhouette is somewhat masculine. It’s helped by tucking the top into the trousers, which gives a little bit of a cinch at the waist. If she wanted to make this a little bit more flirty, she could have a heel instead of a loafer. Actually, this looks like she almost does have a heel. She could do a boot, or a ballet flat, but I would be cautious about how much of the shoe is showing underneath the pant. We do want the shoe to show a little bit and not get lost in the wider leg of this trouser.
19. Silk Scarf with Sweater and Straight-Leg Pants
The silk scarf is definitely a chic, old money accessory. We see it often in the shoulder seasons, but I think it can also come out in summer and winter. It feels almost vintage, which is where it gets its old money quality. It feels like something Audrey Hepburn would be doing.
It definitely has a utility. It does keep your neck slightly warm, and silk is such a great material to have close to the skin.
20. Chocolate Brown Suit with Cream Tank
The chocolate brown isn’t exactly what we would think of as a bold color, but combined this way, it definitely feels like a statement. I like that it’s a little bit oversized here. A suit on women in general feels chic and old money preppy.
It feels professional in a color that isn’t black. It also feels less corporate and more fashion forward.
21. White Poplin Shirt with Khaki Midi Skirt
Khaki is one of our top preppy materials. It feels like a boarding school uniform, maybe a prep school uniform, in the skirt version here. But it feels a little bit less like you were made to wear this because of a dress code obligation. It feels timeless and wearable because of the fit.
It has a little bit of volume, but she’s not lost in the volume because she’s tucking in the button-up shirt. The button-up shirt is definitely also old money chic.
Riding boots, it goes without saying, are definitely preppy and old money. I like that they’ve been having more of a resurgence recently. I think they stand outside of trends, without a square toe or an aggressively pointed toe. Riding boots usually have something in between, especially with their high quality leather and durability. They’re intended, in theory, for riding, so they’ll last you years.
The brown and navy color combination looks rich and understated.
23. Cream Blazer with Black Cigarette Pants
The black cigarette pants also feel somewhat vintage here, almost like a 60s or 70s fit that has never really left us. Cigarette pants can have a longer hem, or they can be a capri like we’ve been seeing more in recent years. With a longer hem, they feel more appropriate over the course of the year, and not just in warmer seasons.
I like that she toned it down with the cream tops, the blazer and the shirt underneath. It looks like both of them fit her very well. The shoulders here hit at exactly the right spot, which is essential for a blazer. Also, ballet flats with cigarette pants are a very vintage, timeless silhouette.
24. Striped Button-Down with Ecru Denim
A button down is definitely old money, especially in a simple pattern like a pinstripe like this. Pinstripes in blue and white are our top preppy option. We also see pinstripes in black and white, but that feels a little bit more modern and edgy than the blue and white, which feels a little bit more coastal and preppy.
Blue, white, and brown leather accessories are very old money coded.
25. Sleeveless Turtleneck with Full Midi Skirt
Again, we have a midi skirt, a full, voluminous skirt here. It has a great full body, and it’s in a lighter color, so I think it allows her to have a little bit more volume with the material, because it’s not an in-your-face color. This outfit has a simple color palette overall. The black and the white together feel understated, but still bold.
The sleeveless black turtleneck is a great option to have if you don’t want the warmer black turtleneck with sleeves. Especially with her ankles showing, it makes sense to have a sleeveless top here.
This is similar to the one we saw above. The color blocking is simple: you match the top color to the bottom color. We have bright on top here, and then darker and warmer in the middle. This is a rich color.
A pleated skirt like this is a great way to add something interesting to your outfit without having to do much. The pleat adds texture, while it’s not actually much to think about. It doesn’t usually need to be ironed or get wrinkled too easily. An accordion pleat is pretty forgiving.
27. Beige Sweater Vest with White Shirt and Trousers
Again, we have the white button-up popping out from underneath a sweater. In this situation, it’s a sweater vest, which is a way to keep warm without too much warmth during fall. It usually doesn’t need to be taken off, and you don’t even have to think about the possibility of taking it off, because they’re pretty cool without the sleeves.
This is a nice neutral color palette with a dark base from the shoes that she’s wearing.
28. Black Blazer with Cream Satin Skirt
Again, we have a midi skirt with color blocking on either side. It’s so chic and easy to throw on. It feels preppy and timeless. The blazer adds a little bit of structure to an otherwise feminine silhouette.
She has a black camisole underneath. She can take off the blazer, and it will feel a lot flirtier than the structure of the blazer.
29. Camel Sweater with White Button-Down and Dark Trousers
Again, the white accents of the button-up shirt popping out of her sweater feel very preppy. It doesn’t feel like too much. It’s definitely a timeless look. I think this top could be paired with almost any bottom that you’d want it to. It could be worn with jeans on more casual days, and it would still feel old money. She could untuck it, and the white button-down would be popping out from underneath as well, which would also look very chic.
This is a very classic silhouette, and an example of pieces that can be thrown into your capsule wardrobe for an old money look: the leather loafers, the white button-down, and a high quality sweater.
Wardrobe Staples From This Post
Timeless pieces behind these classic looks.
- Steve Madden Double-Breasted Trench Coat. The trench from #15, over a white shirt and ankle trousers.
- befen Genuine Leather Tote Bag. A plain cognac leather bag that matches the brown leather accessories in #11.
- PRETTYGARDEN Open Front Oversized Cardigan. A camel cardigan like the one over the black midi dress in #9.
About the Author
Rachel Meyers
Contributing Fashion Creator · Amazon Influencer
Rachel Meyers is a contributing fashion creator for The Better Fit, filming try-ons from Orem, Utah. She has spent three years in the Amazon Influencer Program and is an All-Star contributor in the Viral Vue creator community, and her storefront, Rachel's Reviews and Fun Finds, leans into women's fashion and shoes. Rachel is also a certified life and health coach, and that double life shapes how she reviews: she cares less about how a piece photographs and more about how it feels on a school run, at work, or on the third wear. Her latest try-ons land on YouTube at @rachelsfunfinds.