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Fall/ Winter Fashion, Fashion, Outfits · November 23, 2023

Old Money Aesthetic Style Guide For Winter 2025

Are you tired of not knowing how to dress old money? I got you! This is a comprehensive guide to help you perfect the old-money style & 10 outfit ideas you can easily recreate.

old money style guide

Some links on this page are affiliate links which means if you choose to make a purchase, I may earn a small commission at no extra cost to you. I greatly appreciate your support!

Old money or quiet luxury has become an increasingly popular style in the last few years. Thanks to TV shows like Gossip Girl, Celebrity fashion, and Succession that made this aesthetic a huge trend. 

This style focuses on high quality pieces with minimal logos, timeless designs, and tailored cuts mixed with elegant accessories for that vintage-inspired look. Think tailored suits, trench coats, cashmere sweaters, and monochromatic looks. So, well-made, understated, and timeless pieces are key to being old money. 

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To easily implement this style, we need to understand where the old money aesthetic came from. It’s an aesthetic based around wealthy people who have inherited their wealth instead of working for it. 

Their hobbies include sailing, tennis, horse riding, golfing, and attending polo matches. Which explains why a lot of the outfits we will be talking about today are essentially outfits worn for these activities.

princess diana old money outfit


And while shows like Succession showed us a lot of what this aesthetic is about, I think the epitome of elegance is Princess Diana. who was very famous for her timeless elegance and impeccable style. her ability to effortlessly exude grace and charm made her an icon in the world of fashion. Which is why her outfits are still the best representation of what old money fashion looks like. From power suits to polo shirts, her aesthetic outfits always had that classic style and old money vibe.

Some of the most famous luxury old money brands such as Brunello Cucinelli, Loro Piana, and The Row are quite expensive. The good news is you can still shop this style on a budget. as there are many affordable old money brands that you can shop as well. From mid-range like Ralph Lauren and Banana Republic to a bit lower range like Massimo Dutti, and Tommy Hilfiger. If you want to know more about old money brands, check this article about the top old money fashion brands to shop.

How to achieve the old money look

Don’t worry you don’t have to rob a bank to achieve this style. because while the quality of the clothes matters, what matters more is your taste and unique style. As well as your ability to put simple items together to create sophisticated old money outfits. 

To fully incorporate the old money look, you need to focus on five key elements:

1. Create an old money capsule wardrobe

An old money wardrobe is filled with classic staples that last forever, incorporate classic pieces with your unique personal style to create endless old-money outfits. Most of these pieces you probably already own in your current wardrobe. so, no need for any additional cost. You just need to mix and match these Old Money staples. 

old money winter outfit women

Old money wardrobe includes:

  • Cashmere Sweaters
  • trench coat
  • Pair of loafers
  • button-down shirt
  • pair of high-waisted trousers
  • Blazer 

Accessories:

  • Vintage sunglasses
  • Pearl Necklace
  • Hoop Earrings
  • Silk Scarves
  • Headbands
  • Structured leather bag

2. Quality OVER Quantity

Invest in high-quality pieces that will give you that classic old money style and last you a lifetime. Buying quality pieces doesn’t mean you have to have a huge bank account. There are many affordable options with high-quality materials on the market. You just need to know where to shop and take a closer look on the material list of any piece before you buy. it is always preferable to buy pieces with natural fibers. 

3. Patterns

Avoid bold extravagant prints like animal or floral prints. nothing is wrong with these prints, but these prints give a totally different vibe from the old money aesthetic.  instead opt for graphic prints such as stripes, polka dots, and checks. 

4. Tailoring

It’s very important that you always tailor your clothes, so they fit you perfectly. never too small or too big.  invest in structured high-quality perfectly tailored clothes that suit you like a glove and accentuate your figure. 

5. Colors

Old money style leans towards a neutral color palette, so we see a lot of neutral colors with a pop of color here and there. but to make it easier for you these are popular old money color combinations you can keep in mind when you are putting together your old-money outfits.

old money color combination

Old money outfit inspiration

.1 Monochromatic look

I really resisted including another monochrome look in this guide because I think wearing tonal outfits is the easiest way to have that old-money aesthetic.  

old money monochromatic outfit
@kateehutchins

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.2 Trench Coat, Jeans & Loafers

This is a more casual look, perfect for daytime. Most of us own all the pieces already but I linked some stunning options for you just in case. Plus, the best Loro Piana dupes!

trench coat old money winter outfit
@lovisabarkman

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.3 Cable Knit Sweater & White Shirt 

This is such an easy look to recreate. you can wear it year after year, and it will never go out of style. 

sweater and white shirt old money winter outfit inspo women
@livia_auer

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.4 White Tennis Skirt & Sweatshirt

Remember when we talked about tennis being one of the old money hobbies, so no wonder a white tennis skirt is a must have to achieve the old money look. just pair it with a sweatshirt and some knee-high boots. you can also go for a grey or black skater skirt which can be easier to style during winter with a pair of leggings underneath.

white tennis skirt winter outfit old money
@leximars

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.5 Tweed 2-piece Suit 

For me a matching set is a must-have to achieve that old-money look. especially in tweed because I think tweed gives such a classy look to any outfit.  this would make such a nice formal look paired with a wool coat for colder days.

tweet suit old money

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.6 Black Knit Dress

A black knit dress is a staple for your winter capsule wardrobe. you can add tan/brown accessories or pearl accessories to elevate the look even more. 

black knit dress winter old money outfit

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.7 Blazer & Riding boots

Instead of going for something super oversized, a classic blazer like this just looks so chic. pair it with white leggings and riding boots for the ultimate old money vibe. and we can’t forget accessories! the gold details on the belt add elegance to the look and the statement glasses and black headband add the perfect vintage vibes.

you can also go for a Double-breasted Blazer with gold buttons, I find those super chic and I think a navy blazer with gold buttons paired with neutral colors is also a great option.

blazer and riding boots old money outfit
@ellizabethh

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.8 Checked Blazer & Knit Top

This is the ultimate Ralph Lauren look, a checked/ houndstooth blazer paired with a sweater. this type of pattern instantly gives a more heritage feel to any outfit. You can also layer a white shirt underneath for extra warmth and a vintage touch.

old money winter outfit checked blazer
@heloise.guillet

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.9 Wool Coat & Silk Scarf

Nothing screams old money like a silk scarf! it’s an easy way to add a touch of color to your neutral outfits. You can wear it with a wool coat, a pair of jeans and ankle boots or white trainers.

silk scarf old money outfit
@aaylingk

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.10 Coat, Shirt & Turtleneck

How stunning is this outfit? the colors are the definition of old money, and the striped coat just adds a super chic element to the look. if you love wearing your shirts during winter, it’s always a good idea to layer a turtleneck sweater underneath for extra warmth. 

striped navy coat
@annelauremais

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Posted By: Farah Salem · In: Fall/ Winter Fashion, Fashion, Outfits

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  1. Top Old Money Fashion Brands To Shop - Farah Salem says:
    November 27, 2023 at 12:37 am

    […]  if you want to learn more about old money fashion, check out this old money fashion guide!  […]

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