This post is all about the classiest winter old money outfits for those in their old money fashion era!
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The old-money look is classy, elegant, and refined. It’s the most sought-after style for its symbolism of affluence. The old money style is inspired by the lifestyle of those with immense amounts of wealth. These individuals partake in expensive activities like show jumping, head to boarding school, ski down the slopes of Aspen, or just travel the world leisurely with impeccable style.
These types of activities or lifestyles have won the eyes of many designers one of which is the lovely Ralph Lauren. In addition, a lot of the inspiration for old-money style is timelessness. The classic style has been able to transcend decades of constant change in fashion.
Building an old-money look is not difficult at all. I took the time to create this easy guide of affordable looks to help you find the perfect old-money outfit that will make you stand out this winter season. To start, some of the most popular winter old-money colors are navy blue, brown, black, burgundy, white, etc.
I’ve included looks that I love wearing to casual outings or even to work throughout the winter season. Since I could remember one of my favorite aesthetics was the old-money aesthetic. I would base my style on the preppy or old-money looks a lot of the time. After many years of combining looks that are influenced by this popular aesthetic, I thought I would share some here.
Some of my favorite key pieces to wear for wintertime that are inspired by this aesthetic are a blazer, cable knit sweater with a white button-down, vests, and some wide-leg pants. Once you get the basics down to make some amazing winter old money outfits it’s smooth sailing from there.
Winter Old Money Outfits
1. Old Money Winter Casual
Outfit Details: Turtleneck / Pants / Handbag / Square Earrings / Brown Belt / Tortoise Sunglasses / Low Heeled Boots
Winter casual for this aesthetic is simple and classic. I chose a bright cream color for this look because it highlights the aesthetic of living a classic lifestyle.
You can pair a creme-colored outfit with a gorgeous dark chocolate brown color with accessories and some gold jewelry to really balance out the look.
I also love to wear a gorgeous long coat that covers me up to mid-calf with this look, something like the ones with a belt to wrap around your waist.
2. Winter In Aspen
Outfit Details: Fur Coat / Turtleneck / Wool Leggings / Gold Earrings / Black Leather Gloves / Sunglasses / Snow Boots / Headband
The winter in Aspen look is chic and often includes a gorgeous winter coat. Snowshoes are a must since Aspen is known for its slopes and mountains.
Wear a comfortable turtleneck and some wool leggings to stay warm. Accessorize with gorgeous gold earrings, a black headband, sunglasses, and leather gloves.
If I’m making this outfit look more casual I tend to add some denim pants and some pointy leather heels. I love to wear something like this to dinner or just to go out shopping during the wintertime.
3. Winter Equestrian
Outfit Details: Handbag / Earrings / Blazer / Cable Knit Sweater / White Button Down Shirt / Equestrian Tights / Leather Belt / Waterproof Boots
The equestrian look is sporty and vintage. It’s an elegant and classy look that could be used as a casual outfit.
The best way to style this look is to layer, layer, layer! This is a great way to stay warm in the wintertime. Grab a cable knit sweater, a white button-down, and a blazer to complete this look.
I love layering for the winter! I always make sure to feel comfortable without having the layers look too bulky. A simple tip is to ensure that the garments underneath the coat or blazer are on the thinner side or made of flexible material.
4. Old Money Preppy Style
Outfit Details: Earrings / Loafers / Black Tights / Neck Tie / Wool Skirt / White Collar Shirt / Creme Vest / Black Blazer
The old-money preppy style is inspired by the rich girl in a Switzerland boarding school type of style. Its essence is uniform-like but it can be tailored to your taste.
This style has similar elements to the equestrian look like the white button-down, blazer, and cable knit vest.
For this style, you can either add a skirt to this look or some denim pants to create a more casual look.
5. Winter Old Money Business Casual
Outfit Details: Pants / Long Sleeve Turtleneck / Long Coat / Boots / Black Belt / Gold Hoops / Sunglasses / Red Handbag
The winter old-money business casual look is romantic and edgy. Add elements of uniqueness with a red croc shoulder bag or some 90s-inspired chunky hoops.
This look was a go-to style for me when I was working in my corporate job. I loved wearing a nice turtleneck with a matching coat. Don’t forget to take your nicest boots out of the closet, and dress up this look using some pointy-heeled boots.
6. Feminine & Classic Old Money Style
Outfit Details: Oversized Sweater / Suade Skirt / Black Boots / Black Belt / Earrings / Black Bag / Tights
A classy, simple, yet feminine-inspired outfit for winter is wearing the cutest oversized sweater, a basic black skirt with some 40-den tights.
Accessorize it with some chunky gold earrings, square-toed boots, a thin belt, and a small shoulder bag.
This is a look that I wear anywhere especially if I’m going to a semi-casual event in the winter. Also, if I’m not wearing it with a skirt then I’m most probably wearing it with some nice black leather pants.
7. Charming & Cute Old Money Style
Outfit Details: Cardigan Sweater / Wide Leg Pants / Earrings / Ring / Bracelet / Black Handbag / Two-Toned Flats
This style is inspired by Chanel with its classy looks and its elegant accessories. Wear this look with a turtleneck underneath and a long black coat for those really frigid days.
You can dress the look up with a skirt and some black tights for a semi-casual party or gathering. If the wide-leg pants are too thin for the winter, I would highly suggest wearing some wool tights or pantyhose underneath.
8. Minimalist Old Money Style
Outfit Details: Grey Sweater / Khaki Pants / Gold Watch / Waist Belt / Croc Flats / Black handbag
If you love the old-money look but you also love minimalism this look is for you! It’s easy to style and can be used for a casual gathering or it can also be a work outfit inspiration.
When I worked in corporate, I loved wearing these types of winter old money outfits during those really cold days. I usually added a long wool coat with a thick scarf to keep me warm.
9. Old Money Glamour
Outfit Details: Fur Coat / Black Dress / Fleece Tights / Black Headbands / Black Sunglasses / Gold Earrings / Black Boot / Brown Bag
Everyone wants to wear the old-money glamour look that is very similar to the “Mob wife aesthetic look”. It’s all about the fur coats, the statement jewelry, and the fancy-heeled shoes.
This look is perfect to wear to a party or a special occasion during the winter. It’s elegant and chic and it will most definitely make heads turn.
If wearing a fur coat is too much for you then adding a beautiful long coat that wraps around the waist is just as glamourous.
{Related Post: The 18 Most Glamorous Mob Wife Aesthetic Outfit Ideas}
10. French Inspiration
Outfit Details: 2 Piece Suit / Beret / Tights / Watch / Earrings / Shoulder Bag / Boots
The last look is the old-money French inspirational look. It’s a look inspired by French fashion like the baret. It’s flirty and fun yet chic and simple.
This clean look pairs well with a fur coat or a wool coat to finish off the look. If it’s too cold outside, I would add a turtleneck underneath the blazer.
Accessorize with pearl vintage earrings, a small and thin gold watch, and a cute soft beret to tie this look together!
The old-money aesthetic has taken over our wardrobes. For me, it has always had a special place in my heart despite not knowing this type of style had a name.
It’s a chic and classic look that will keep capturing the hearts of many in the years to come because it prefers quality and tradition over trends.
These have been some of my favorite looks to wear during the wintertime time. They have been my go-to winter old money outfits for a while now, and I hope that you love them as much as I have.
