You loved our roundup of summer old money outfits—now it’s time to step into fall like you just inherited another estate. Think cozy layers, rich textures, and fall outfits that say, “I’ve never checked a price tag in my life.” Ready to serve serious autumn wealth vibes? Let’s do this.
1. Half-Zip Sweater & High-Waisted Jeans
A cream half-zip sweater paired with high-waisted jeans is giving serious “my yacht is bigger than your house” vibes. The neutral palette is clean and sophisticated, while the half-zip detail keeps it just relaxed enough. Add a brown leather belt and you’re ready to sail through fall in style.
2. Cropped Jacket & Pleated Trousers
Why choose between classic and modern when you can have both? A cropped brown jacket paired with pleated gray trousers gives off a vibe that says, “I inherited my fashion sense along with my trust fund.” Understated fall luxury at its finest.
3. Cable-Knit Sweater with Shirt & Trousers
There’s something so perfectly preppy about a cable knit sweater layered over a white shirt. Paired with tailored trousers, this look is giving Ivy League alumni who just casually happens to be a CEO. It’s cozy, classic, and just the right amount of snobbish.
4. Gray Cable-Knit Sweater & Matching Trousers
The matching cable-knit sweater and trousers are basically loungewear for the fabulously wealthy. Top it off with burgundy heels, and you’re giving off “I own several horses and an estate to match” vibes. Comfort has never looked so expensive.
5. Checked Blazer with Turtleneck & Trousers
Nothing says old money like a houndstooth blazer over a creamy turtleneck. The brown trousers tie it all together in the most “I own three racehorses” kind of way. This look is perfect for that fall stroll through your family’s sprawling estate (or, you know, the nearest park).
6. Plaid Blazer with Turtleneck & Pants
Classic, timeless, and just a bit British—a brown plaid blazer with a cream turtleneck and pants is like walking around with an aura of generational wealth. Coffee in hand, of course, because what’s a rich girl fall without a Starbucks accessory?
7. Beige Jacket with Turtleneck & Jeans
A beige jacket over a white turtleneck is giving off serious “weekend in the Hamptons” vibes. The high-waisted jeans keep the look polished, and a sleek belt adds just the right amount of detail. Throw on some oversized sunglasses, and you’re basically a Kennedy.
8. Coat with Houndstooth Lapels & White Pants
When a regular camel coat just isn’t enough, you add houndstooth lapels, obviously. This outfit is peak old money fall—polished, poised, and perfect for your next trip to the country club. The white pants and turtleneck keep it clean and classy, while the coat adds that touch of aristocratic flair.
9. Camel Coat with Striped Shirt & Trousers
Pair a camel coat with a blue striped shirt and high-waisted white trousers for an early fall look that serves some serious “I own the yacht” vibes. The coat’s neutral tone is timeless, while the shirt adds just enough preppy contrast. High-waisted trousers? Always classy, always in charge.
10. Black Coat with Turtleneck & Trousers
A black coat over a black turtleneck with wide-leg trousers is the definition of stealth wealth. The maroon bag adds just the right pop of color, keeping the look chic but far from boring. Perfect fall look for when you want to give off those “I’m too important for this” vibes.
11. Chunky Knit Sweater & Brown Trousers
A chunky knit sweater paired with high-waisted brown trousers is like wrapping yourself in fall. It’s cozy, it’s chic, and it’s exactly what you wear when you’re about to spend the weekend at the Cotswolds. Or just pretending you are.
12. White Button-Up with Sweater Vest & Trousers
Nothing says “I’m from old money” like a perfectly layered preppy fall look. The white button-up and a sweater vest combo is s polished, it’s refined, and it’s exactly what you wear when you want to look effortlessly put together.
13. Belted Cape Coat with Turtleneck
A cape coat? Now that’s how you show the world you’ve got some old-school glamour going on. Belt it at the waist, throw on a black turtleneck underneath, and suddenly, you’re the mysterious heiress everyone’s dying to know more about.
14. Camel Coat & Striped Sweater
If your autumn aesthetic is “weekending at the country estate,” then this outfit is your blueprint. The camel coat over a navy striped sweater nails that preppy, old money vibe. Khaki pants keep it grounded while still giving off that effortless wealth.
15. Grey Coat Over Layered Knit
This is your “I’m off to close a six-figure deal and then grab coffee” look. The gray coat over layered knits and trousers is both functional and fashionable. It’s understated, but in a way that says, “Yes, this is all designer, but I’m not one to brag.”
16 Cream Cable-Knit Sweater & Trousers
Monochrome cream is the ultimate rich girl move. This cable-knit sweater and high-waisted trousers combo is as luxurious as it gets without trying too hard. It’s the kind of outfit that says, “Yes, I do have my life together, thanks for asking.”
17. Checked Blazer & Vest with Denim Layering
Layering done right is a sure sign of old money style, and this outfit is layering perfection. The checked blazer and matching vest over a denim shirt scream country manor meets city sophistication.
18. Black Coat with Turtleneck & Tan Trousers
This look is basically “I own the building, not just the apartment” energy. The black coat and turtleneck combo is as classic as it gets, but throw in those high-waisted tan trousers and suddenly you’re a walking hedge fund.
19. Cable Knit Cardigan & Matching Skirt
This look is basically your grandma’s cozy cardigan—if your grandma was a European duchess. The matching cable knit set in that rich, caramel hue? Perfection. It’s comfortable enough for lounging in your private library but polished enough for afternoon tea at the Ritz.
20. Tweed Blazer with Turtleneck and Trousers
This is the outfit you wear when you want to channel your inner English aristocrat. The tweed blazer over a dark green turtleneck is giving major “I went to Oxford” vibes, while the wide-leg trousers keep it modern and chic.
SEE ALSO: Dark Academia & Light Academia Outfit Roundups
When done right, a navy blazer and a crisp white shirt combo is everything old money preppy dreams are made of. Cinch that waist with a brown belt, and let everyone know you’re not here to play.
This houndstooth blazer is practically screaming “old money trust fund.” Layered over navy basics, it’s the perfect mix of classic and cool. Throw on some oversized sunglasses and you’re ready to grab a coffee while ignoring paparazzi.
23. Turtleneck Sweater with Black Skirt
This cream turtleneck paired with a black skirt is basically a trust fund in outfit form. The minimalist vibes are a subtle nod to old money elegance, and those gold accessories? Just enough to say, “Yes, I do have a financial advisor.”
SEE ALSO: Silk Skirt Outfit Ideas to Amp Up Your Style
24. Plaid Blazer with Brown Collar & Black Boots
A plaid blazer with brown collar and black riding boots combo gives off major equestrian club energy. Whether or not you’ve ever been near a horse, this outfit will have people convinced you’ve won a few ribbons. It’s heritage style with a modern twist.
25. Brown Jacket & Pleated Skirt
A pleated gray skirt with a brown jacket? It’s basically the uniform for sipping lattes while your stock portfolio grows. The whole vibe is muted luxury—nothing says old money like dressing down in top-tier fashion.
26. Plaid Belted Vest & Puff Sleeve Blouse
A plaid belted vest over a white puff sleeve blouse is how you do business casual the old money way. Paired with sleek trousers and a polished handbag, it’s perfect for brunch at the country club. Or, you know, ruling the world.
27. Tailored Grey Coat & Plaid Trousers
Tailored gray coat? Plaid trousers? You might as well start drafting your will because this look is pure inheritance. It’s crisp, it’s clean, and it’s exactly what you wear when you want people to know your art collection could fund a small country.
28. Layered Camel Cape with Plaid Blazer
Throwing a camel cape over anything instantly makes you 100% more mysterious and 200% more fabulous. Layer it over a plaid blazer, and you’re basically walking wealth. Just make sure to practice your disinterested stare—it’s essential when your outfit is this flawless.
29. Blazer with Striped Shirt & Corduroy Trousers
A navy blazer paired with a striped shirt and brown corduroy trousers is giving all the autumnal richness you need. The woven belt is a nod to heritage style, while the oversized sunnies add a dash of “don’t talk to me, I’m busy owning several properties.”
30. Textured Blazer & Black Pants
This all-black look is serving “I own the bank” vibes. That textured blazer with gold buttons? Pure wealth. Black pants? Power move. Add that sleek handbag, and you’ve just upgraded your “Don’t talk to me” energy to billionaire status.
There you have it! Ten old money fall outfits that practically ooze sophistication and wealth. Now go flaunt that autumn wardrobe like you just closed a deal on a new country manor.
