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If fall fashion had a trust fund, this would be it. Old money style is all about looking effortlessly polished—like you just stepped off a horse, into a Range Rover, and casually into a cashmere-clad life of understated luxury.
Think neutral tones, classic tailoring, and fabrics that whisper, “I don’t check price tags.” Whether you’re heading to class, brunch, or simply romanticizing your errands,
These fall old money outfits will have you looking like autumn royalty—no inheritance required.
1. fur jacket + fiited top + pleated pants
Pairing a luxurious faux-fur jacket with sleek pleated pants not only keeps you warm but also exudes that “rich aunt at a ski chalet” vibe.
2. Layering is the key
Channel the ultimate layered fall look with a trench coat draped effortlessly over a cozy sweater. Add a striped shirt for a preppy touch, along with tailored shorts and a minimalist baseball cap for that sporty-chic feel.
3. sweater vest over shirt + pleated pants
Layer a cable-knit sweater vest over a button-down shirt, and style it with pleated trousers in a neutral tone. Sneakers are a must for this look.
4. blazer over shirt dress
A tailored blazer over a flowy shirt dress strikes the perfect balance between power dressing and casual sophistication. Opt for earthy tones like brown or olive green.
5. knit sweater + tailored pants
Pair a high-quality cable-knit sweater in a neutral shade with tailored pants, and you’ve instantly achieved a clean, chic look. Add delicate gold jewelry and pointed-toe flats or loafers.
6. blazer + shirt + mini skirt
For a youthful spin on the old money aesthetic, style an oversized blazer over a crisp button-up shirt and a mini skirt. Keep it classy with neutral tones and pair with tights to stay warm.
7. knit sweater over shirt + mini skirt
Layer a chunky-knit sweater over a button-up shirt with a pleated mini skirt peeking out. This look is perfect for pumpkin patch visits or casual dinner plans.
8. loose jumper + satin maxi skirt
For ultimate comfort with a touch of elegance, pair a loose knit jumper with a silky satin maxi skirt. The contrast of textures is what makes this look like a showstopper.
9. sweater vest over shirt + pleated pants
Take inspiration from classic menswear with a modern twist. Combine a sleeveless sweater vest with a crisp button-up and tailored pleated pants. This timeless combo works perfectly with loafers and a structured handbag.
10. loose jumper + pleated mini skirt
To combine warmth and cuteness, throw on an oversized jumper over a pleated mini skirt for that effortlessly chic vibe. Style it with knee-high socks, and finish with a pair of preppy loafers for a playful edge.
11. long coat over sweater vest and shirt + pleated skirt
Start with a long, tailored coat over a sleek vest and a shirt and pair it with a pleated skirt in neutral tones. It’s giving modern prep school vibes with a grown-up twist.
12. long coat over cozy jumper + jeans
Pair a chic, long wool coat with a cozy jumper and a pair of straight-leg jeans for an effortlessly rich look. Add your fave sneakers and matching baseball cap, and you’re ready for brunch or a casual weekend stroll.
13. trench coat + jumper over shirt + mini skirt
Your trench coat deserves the spotlight this fall. Layer it over a jumper worn atop a crisp button-up shirt and a cute mini skirt for a balanced blend of smart and flirty.
14. knit sweater over shirt + tailored pants
A chunky knit sweater layered over a button-down shirt, paired with tailored trousers. Think creamy whites, earthy taupes, and warm grays. Complete the outfit with classic loafers and minimal gold jewelry.
15. leather jacket over fitted top + pleated pants
A well-fitted leather jacket layered over a sleek top paired with a pleated midi skirt gives you a perfect mix of tough and feminine. Finish it off with combat boots and a structured handbag for an undeniable old money meets rebel aesthetic.
16. striped blazer over shirt dress
Shirt dresses are a fall favorite, and adding a blazer takes it to the next level. A crisp, structured blazer in a greyish tone over a striped shirt dress creates a polished yet relaxed vibe. It’s giving the CEO a heading straight to the farmer’s market feels.
17. trench coat over cozy sweater + mini skirt
Wear a trench coat over a snug sweater and mini skirt combo. Opt for muted tones and a chic pattern like houndstooth for an ultra-preppy vibe – think fall networking event or an art gallery date.
18. sweater over striped shirt + pants
A sweater over a striped button-up immediately says “wealthy understatement.” Pair with loose-fitting trousers for a relaxed yet tailored vibe. Slip into loafers or chunky mules, and add statement earrings to bring it all together.
19. loose jumper + leopard mini skirt
Add a dash of personality with a loose oversized knit paired with a leopard-print mini skirt. The bold pattern gives this outfit an approachable yet elevated edge.
20. long coat + knit sweater + pants
Start with a long coat in an earthy tone, add a luxe knit sweater, and finish with tailored wide-leg trousers. Stick to a neutral palette for that rich, textured look.
