Fake the Old Money Aesthetic With These Rich-Looking Winter Outfits
Your guide to wealthy dressing awaits.
I love nothing more than dressing for winter, mainly because chilly temperatures invite endless layering options, from snug knit sweaters to luxe shearling-lined coats. Now that the cold-weather months have finally arrived, I’m beginning to round out my rotation of looks that will keep me warm. But I’m not just searching for any old, toasty uniform—I’m anchoring my closet with rich-looking outfits that will carry me through the season in style.
When I say “rich,” I’m referring to the viral, quiet luxury aesthetic defining the sought-after wardrobes of A-listers like Mary-Kate and Ashley Olsen, Zoë Kravitz, and Jennifer Lawrence. The same old money trend has spilled into the street style scene, where fashion It girls are dressing in perennial classics like cardigans stitched with soft cashmere and trench coats cut from lustrous leather. Given that I’m drawn to anything that screams “stealth wealth,” I’ll follow their sartorial lead.
Ahead, you’ll get a sneak peek into my winter mood board, featuring sophisticated styles that will make you look like you’ve won the lottery. You’ll find a range of looks from relaxed checked coats styled with loafers to upscale knit dresses paired with kitten heels.
Luxe Leather
Invest in a leather coat that embodies the phrase "effortlessly elegant.”
When crafting an elevated outfit, it’s essential to prioritize quality fabrics. A coat designed with glossy leather is always a great place to start. Earn extra style points if you lean into the latest color trends (I’d recommend a deep mulled wine shade).
All in the Details
Stand out among the crowd by way of a winter coat made with bold collars.
For those who think all-black outfits are boring, the look above will convince you otherwise. Decorated with intricate collars, this frilly layer commands attention. Dress it up even further with a handbag and gold jewelry.
Check the Boxes
This casual look still manages to flaunt an elevated edge.
If you're aiming for a laid-back look, slip into a playful checked coat with an ankle-grazing hemline. Ground your getup with chunky loafers styled with socks to give your rich-looking outfit a preppy feel.
Oh-So Timeless
Wear Burberry’s iconic plaid scarf and you’ll instantly give off a cultivated aura.
Want a cold-weather outfit that will prevail season after season? Take a look at this classic ensemble rooted in neutrals. Zhuzh things up with a cashmere scarf plastered in plaid.
Matchy-Matchy
You’re guaranteed to rely on this uncomplicated outfit formula.
Looking rich doesn't have to be complicated. In fact, one of the easiest ways to radiate wealth is to slip into a polished set that will make you look put-together. Throw a pop of red into the mix if you want to break things up a bit.
Run Wild
A true fashion connoisseur will note that you can style an animal print coat as you would any other neutral layer.
Although the leopard print trend is certainly having a moment, it’s always been around. And truth be told, this feral style isn’t going anywhere. Test-drive the look with a spotted coat and stick to a brown color palette for the rest of your outfit.
The Trending Sneaker
Sneakers can look rich too!
Without question, Adidas Samba sneakers have continued to dominate the shoe trends cycle. Although the black-and-white colorway is arguably the most popular version, why not experiment with other hues? Take notes from this stylish fashion week showgoer and opt for burgundy.
All Dressed Up
A night on the town calls for a glamorous knit dress.
Within your assortment of rich-looking outfits, a winter dress should take center stage. Team a knitted frock with a leather trench coat and you’ve got yourself an eye-catching holiday party outfit. Slide into a pair of kitten heels in lieu of sky-high platforms if you plan to be on your feet all night long.
Monochromatic Dressing
Master a refined look by wearing a classy shade of earthy brown from head to toe.
Whether you’re heading into the office or grabbing drinks with friends, consider this straightforward camel-colored outfit for your next formal outing. Achieve a prim and proper look by adhering to a monochromatic agenda.
Comfort Is Key
With a uniform that’s this simple to recreate, you’ll find yourself becoming an outfit repeater.
If your personal style is characterized by a strong sense of comfort, copy this look for a cozy cold-weather outfit. And if you’re willing to embrace a trend while you’re at it, try out a pair of riding boots that will offer a charming English country-style twist.
Two-Toned
The trusty black-and white uniform boasts an enduring color combination that will never fail.
When in doubt, you can always count on an easygoing black-and-white outfit to get the job done. Pull on a pair of smooth leather gloves and channel your “ladies who lunch” persona.
A Durable Layer
Here’s your sign to try out the viral barn jacket trend.
Yes, you can style a barn jacket for occasions beyond visiting any stable or farm. Simply coordinate your sturdy layer with a pair of cuffed jeans and striking boots.
