Winter is HERE, babe, and you know what that means, time to SLAY the cold in style! These 43 Old Money Winter Outfits are serving cozy, chic, and full-on “I vacation in Aspen” vibes. Think cashmere coats, leather jackets, and those effortless layers that scream, “I don’t chase, I attract.”
This isn’t just about staying warm; it’s about serving looks while doing it. Whether you’re sipping hot cocoa at a chalet or just strutting to Starbucks, these outfits are giving MAJOR main character energy.
So, let’s grab our latte, throw on a long coat, and dive into winter glam.
1. Long Brown Coat Over White Layers Styled With Sambas
Okay, first of all, this look screams effortlessly rich aunt vibes! The crisp white layers paired with a classic brown coat? It’s like, “Oh, I just threw this on” but also looks like a Pinterest board came to life. And those Sambas? LOVE. Sporty and luxe at the same time.
2. Chic Black Fur Coat & Classy Boots
Ummm, HELLO luxury! This black fur coat paired with boots is giving “stepping out of my G-Wagon for a coffee run” energy. So sleek, so chic, so old money it hurts.
3. Chocolate Brown Cashmere Coat
Old Money Outfit
Chocolatey goodness, anyone? This coat is sooo soft-looking, it’s practically a hug in outfit form. Imagine wearing this while sipping hot cocoa at a ski lodge. Yes, girl, YES.
4. Korean Long Grey Coat Fit
STOP. This outfit is such a vibe! The grey coat is super polished but still cozy, and we all know the Koreans know how to serve minimalist chic. Obsessed is an understatement.
5. Old Money Brown Leather Jacket & Jeans
Who said leather can’t be classy? This fit is so rich and laid-back. Perfect for those “I’m just running errands but still slaying” moments. Pair it with some gold hoops, and girl, you’re ready to conquer.
6. Classy Long Sweater & Long Boots
Comfy but make it classy! The long sweater paired with boots is just… chef’s kiss. It’s like being wrapped in a chic blanket but make it fashion. Boots up to the knee? Yasss queen, strut!
7. White Russian Rich Old Money Style
OMG, THIS. It’s giving “winter wonderland meets Russian heiress.” The whites-on-whites are just soooo dreamy. Snow queen vibes, anyone?
8. Burgundy Jumpsuit & Leopard Long Coat
Burgundy + leopard? That’s the drama we need in our lives! This look says, “I’m not afraid to turn heads.” It’s bold but soooo elegant at the same time. LOVE.
9. Old Money Fur Coat Style
This fur coat is just gorgeous. Like, imagine stepping into a chic soirée in this. Everyone’s jaws will drop, trust me. SO classy and timeless.
10. Trench Coat & Old Money Hat Fit
Ugh, trench coats and hats? Name a better duo, I’ll wait. This look is so vintage and iconic. You’ll feel like you just stepped out of a Parisian movie scene. Oui, oui!
Bonjour la perfection!
11. Caramel Cashmere Coat & Long Boots
The caramel tones of this coat are everything. It’s warm, luxurious, and screams, “I brunch at places you’ve never heard of.” Pair it with those long boots, and you’re golden, babe!
12. Classy Heels & Jeans With Old Money Leather Jacket
YASSSS, we love a mix of classy and casual! Those heels add just the right touch of glam to the leather jacket and jeans. Perfect for dinner dates or casual cocktails.
13. Blue Jeans & Black Long Coat
Simple but sooo effective. This is giving that “cool girl” energy with a touch of mystery. Black and blue together? Always a win.
14. Classy Burgundy Top With Mini Skirt
STAWWWWP, this is giving that girl energy. Burgundy is always so rich-looking, and the mini skirt adds a flirty touch. Pair it with some tights for winter, and you’re unstoppable.
15. Beige & White Old Money Fit
Beige and white together are so underrated. It’s soft, elegant, and screams “cozy afternoon at a private library.” Add a latte, and you’ve got the whole vibe.
16. Dark Feminine Old Money Look
Old money blue shirt, brown long coat and a touch of mystery. This look says, “I have secrets, and I keep them stylish.” A total power move for winter fashion.
17. Wide Leg Jeans & Classy Old Money Short Coat
Wide-leg jeans make everything look cooler, period. Paired with a chic short coat? It’s giving effortless luxury. Perfect for a day out shopping or a casual meet-up.
18. Burgundy & Beige Old Money Look
Burgundy and beige together? SO GOOD. It’s like warm and bold met and decided to become iconic together. This look is just rich, period.
19. Blue Long Coat Paired with Burgundy Layers
Okay, the contrast here is everything! The rich blue with the deep burgundy underneath is just chef’s kiss. It’s bold yet so classy. LOVE THIS.
20. Light Long Trench Coat & Blue Jeans Fit
Trench coats are just timeless, and with blue jeans? You’re ready for anything! This look is casual enough for errands but polished enough for brunch. Iconic!
21. Cozy Old Money Winter Outfit
Okay, this outfit feels like getting a hug from a cozy blanket. SO snuggly, yet it whispers, “Yes, I do have a trust fund, why do you ask?” Perfect for sipping mulled wine by a roaring fire.
22. Sheep Wool Jacket & Blue Jeans Outfit
BRB, Googling how to look this cozy and chic at the same time. Like, I want to be wrapped in sheep wool forever, but make it fashion. Also, the jeans keep it cute and down-to-earth. We love versatility!
23. Brown Long Coat Paired with Black Layers & Sambas
This is like, “I’m running late to my art gallery opening, but my outfit is still on point.” The Sambas make it sporty chic, and the brown and black? OMG, a match made in winter heaven.
24. All Black Classic Blazer Fit
Do I feel like a boss babe in this, or do I feel like a villain in a spy movie? Both? Okay, cool. Black-on-black is always a vibe, and this blazer fit is the power move we all need.
25. Burgundy & Leopard Pants Outfit
STOP IT RIGHT NOW. Burgundy AND leopard? This outfit is giving rich aunt who vacations in Monaco. It’s bold, it’s playful, and honestly, I want it in my wardrobe ASAP.
26. Mix Of Classic & Casual Old Money Outfit
Okay, imagine this: you’re at a fancy coffee shop, sipping a $20 cappuccino, and everyone’s staring because this outfit is IT. A mix of classic and casual? Perfect for dominating the streets (and Instagram).
27. Shaggy Beige Coat Old Money Outfit
Is it a coat? Is it a walking cloud? Who cares because it’s STUNNING. This shaggy coat is so cozy, you’ll feel like a marshmallow—but a chic marshmallow who gets invited to exclusive winter galas.
28. Vintage Leather Jacket & Wide Leg Pants Fit
Leather jacket + wide leg pants = the ultimate cool-girl formula. Add a vintage vibe, and suddenly you’re starring in your own Netflix series about a mysterious heiress. (CALL ME, NETFLIX!)
29. Cozy Old Money Fit With Campus Adidas
I don’t know who decided Adidas would be the go-to shoe for old money winter outfits vibes, but they deserve a standing ovation. This look is laid-back yet so polished. You’ll look like you just casually own a vineyard or two.
30. Classic Old Money Outfit
Oh, just your standard I-own-a-yacht fit. This outfit is timeless, elegant, and literally impossible to mess up. It’s like, if old money winter outfits had a uniform, this would be it.
31. Chic With All Black & Mini Grey Skirt Fit
Okay, first of all, this outfit is so flirty and fun. The all-black keeps it chic, but the mini grey skirt says, “I’m cute, but don’t test me.” Throw on some sheer tights, and girl, you’re unstoppable.
32. Cozy Old Money Outfit With Burgundy Heels
Can we talk about burgundy heels for a sec? They’re SO underrated. Pair them with a cozy fit, and you’re out here serving looks while staying warm. Honestly, iconic.
33. Cozy Sporty Old Money Style
This one is perfect for when you want to look like you care, but not too much. Think casual errands but with an aura of, “I have a private chef, thanks.”
34. Leopard Fur Coat & Skinny Jeans
This leopard coat is giving, “Yes, I’m the drama.” Paired with skinny jeans? It’s a look that says, “I run this town, but I’m approachable.” Honestly, iconic energy.
35. Long Grey Coat & Jeans Fit
This outfit feels like wrapping yourself in a hug from a stylish grandpa. It’s cozy, it’s sophisticated, and it’s perfect for all your winter errands. Add a scarf, and you’re golden, babe!
36. Tweed Jacket & Cutie Mini Skirt
OMG, tweed is the epitome of old money winter outfits. Pair it with a mini skirt, and you’re officially channeling Clueless vibes but with a winter twist. AS IF we could ever resist this look!
37. Vintage Leather Jacket Fit For That Old Money Look
This jacket is screaming, “I was found in a Parisian thrift store, and now I’m worth a million dollars.” Pair it with tailored pants, and you’re giving mysterious art collector vibes.
38. Long Fur Coat Rich Outfit
STOP, I can’t. This fur coat is dripping in luxury. You’ll look like you stepped out of a black-and-white movie about high society. Grab a red lip, and you’re ready for your close-up.
39. Parisian Burgundy Old Money Outfit
Anything Parisian gets an automatic 10/10 from me, but this burgundy number? UGH, it’s too good. It’s chic, romantic, and perfect for strolling down cobblestone streets.
40. Cozy Old Money Outfit With Grey Long Coat & White Layers
This outfit is just pure comfort goals. The grey coat is sophisticated, and the white layers underneath keep it fresh. Perfect for casual winter days when you still want to slay.
41. Classy Long Coat With Short Skirt & Long Boots
HELLOOO, this is giving “I run the family empire, but I still have time for brunch.” The long boots scream power, the short skirt adds sass, and the coat ties it all together. BRB, recreating this for a coffee date.
42. Grey Long Coat & Black Short Skirt
This combo is like Audrey Hepburn but with a winter twist. It’s elegant, minimal, and SO versatile. Add some ankle boots and a beret, and you’re basically Parisian royalty. Tres chic, non?
43. Girly & Cozy Old Money Mini Skirt Fit
Okay, this outfit is adorable AND luxe. The mini skirt says playful, while the cozy sweater says “I know how to layer, sweetie.” Pair it with knee-high socks for that prep school but make it fashion vibe.
For You Girls
And that’s a wrap on these 43 Old Money Winter Outfits! Like, can we all agree that winter is officially the season for being cute AND classy? Whether you’re channeling your inner royalty in a fur coat or rocking those cozy Sambas with layers for days, you’re bound to turn heads, babe.
Now tell me, what’s your go to old money winter outfits vibe? Are you a trench coat girly or all about that sweater life? Let’s keep the fashion convo going in the comments. And don’t forget: winter is the time to shine bright like a snowflake.
Stay chic, stay warm, and slay, always!
