**26 Chic & Timeless Fall Outfits for Women: Embrace the Old Money Style**

As autumn approaches, it’s the perfect time to refresh your wardrobe with stylish and timeless outfits. Embrace the sophisticated charm of old money fashion with our curated list of 26 chic fall outfits for women. These looks blend classic elegance with contemporary flair, offering a refined approach to seasonal style. Here’s how you can embody the old money aesthetic and stay fashion-forward this fall.

### **1. Tailored Wool Blazer**

A tailored wool blazer is a staple in old money fashion. Opt for a neutral color like beige, navy, or gray. Pair it with high-waisted trousers and a silk blouse for a polished look. This versatile piece can be dressed up or down, making it a must-have for any fall wardrobe.

### **2. Classic Trench Coat**

The trench coat is a timeless outerwear piece that exudes sophistication. Choose a classic beige or navy trench with a belt to cinch the waist. This coat effortlessly layers over dresses, skirts, and trousers, providing both warmth and style.

### **3. Cashmere Sweater**

Invest in a high-quality cashmere sweater in a neutral or muted tone. This luxurious fabric not only keeps you warm but also adds a touch of elegance to any outfit. Pair it with tailored trousers or a midi skirt for a refined look.

### **4. Plaid Skirt**

A plaid skirt is a quintessential old money piece. Opt for a high-waisted, knee-length skirt in classic plaid patterns. Combine it with a crisp white blouse and knee-high boots for a chic and preppy fall outfit.

### **5. Silk Scarf**

Add a silk scarf to your ensemble for a touch of luxury. Choose a scarf with a classic pattern, such as paisley or houndstooth, and drape it around your neck or tie it to your handbag. This accessory enhances any outfit with a dose of sophistication.

### **6. Wool Midi Dress**

A wool midi dress is perfect for fall. Look for a dress with a fitted bodice and flared skirt in a neutral or jewel tone. This elegant piece can be paired with tights and ankle boots for a polished, seasonal look.

### **7. Leather Loafers**

Leather loafers are a stylish and practical footwear choice. Choose loafers in classic colors like black or brown. These shoes are perfect for both work and casual outings, providing comfort and timeless style.

### **8. High-Waisted Trousers**

High-waisted trousers are a versatile wardrobe essential. Opt for trousers in a neutral color or subtle pattern. Pair them with a fitted sweater or blouse for a sophisticated look that effortlessly transitions from day to night.

### **9. Cable Knit Sweater**

A cable knit sweater is a cozy and classic fall staple. Choose a sweater in a soft, neutral color and pair it with jeans or a pencil skirt. This timeless piece adds texture and warmth to your fall outfits.

### **10. Wool Felt Hat**

A wool felt hat adds a touch of old-world charm to your look. Opt for a classic fedora or wide-brimmed hat in a neutral shade. This accessory not only keeps you warm but also elevates your fall style.

### **11. Double-Breasted Blazer**

The double-breasted blazer is a stylish and sophisticated option for fall. Choose a blazer in a classic color like navy or gray. Pair it with a simple blouse and tailored pants for a chic, office-ready outfit.

### **12. Tweed Jacket**

A tweed jacket embodies the classic old money aesthetic. Opt for a tailored jacket in a subtle tweed pattern. This piece adds texture and sophistication to your fall wardrobe, perfect for layering over dresses or blouses.

### **13. Leather Pencil Skirt**

A leather pencil skirt is both edgy and elegant. Choose a skirt in a classic black or brown hue. Pair it with a tucked-in blouse or sweater for a look that is both refined and contemporary.

### **14. Cashmere Cardigan**

A cashmere cardigan is a luxurious addition to any fall outfit. Opt for a cardigan in a neutral color and layer it over dresses or blouses. This versatile piece adds warmth and sophistication to your look.

### **15. Suede Ankle Boots**

Suede ankle boots are a stylish and practical footwear option for fall. Choose boots in a neutral or earthy tone and pair them with skirts, dresses, or trousers. These boots provide comfort and a touch of elegance.

### **16. A-Line Dress**

An A-line dress is a timeless silhouette that flatters all body types. Opt for a dress in a rich fall color or classic pattern. Pair it with tights and ankle boots for a sophisticated and seasonally appropriate outfit.

### **17. Cashmere Wrap**

A cashmere wrap is both stylish and cozy. Choose a wrap in a classic color and drape it over your shoulders for an extra layer of warmth. This versatile accessory can be worn with a variety of fall outfits.

### **18. High-Neck Sweater**

A high-neck sweater is perfect for keeping warm while looking chic. Opt for a sweater with a subtle pattern or in a classic color. Pair it with tailored trousers or a skirt for a polished fall look.

### **19. Wool Wide-Leg Pants**

Wool wide-leg pants are a sophisticated and comfortable option for fall. Choose pants in a neutral color and pair them with a fitted sweater or blouse. This silhouette adds a touch of elegance to your wardrobe.

### **20. Structured Handbag**

A structured handbag adds a touch of sophistication to any outfit. Opt for a classic design in a neutral color. This accessory is both practical and stylish, perfect for carrying your essentials.

### **21. Turtleneck Dress**

A turtleneck dress is both cozy and chic. Choose a dress in a rich fall color or classic black. Pair it with knee-high boots and a belt to create a flattering silhouette.

### **22. Wool Blazer Dress**

A wool blazer dress combines the elegance of a blazer with the versatility of a dress. Opt for a tailored fit in a classic color. This piece can be worn alone or layered with tights and boots for a sophisticated look.

### **23. Checkered Blazer**

A checkered blazer adds a stylish twist to your fall wardrobe. Choose a blazer in classic checkered patterns and pair it with tailored trousers or a skirt. This piece adds a touch of sophistication and interest to your outfit.

### **24. Cashmere Beanie**

A cashmere beanie is a luxurious and practical accessory for fall. Opt for a beanie in a classic color to keep warm while adding a touch of elegance to your look.

### **25. Pleated Midi Skirt**

A pleated midi skirt adds movement and sophistication to your fall outfits. Choose a skirt in a rich fall color and pair it with a fitted sweater or blouse for a chic, elegant look.

### **26. Monochrome Outfit**

A monochrome outfit in classic fall colors, such as beige or navy, exudes timeless elegance. Opt for pieces in varying shades of the same color to create a cohesive and sophisticated look.

### **Conclusion**

Embrace the sophistication and timeless charm of old money style with these 26 chic fall outfits. From tailored blazers and cashmere sweaters to classic plaid skirts and elegant accessories, these looks offer a refined approach to seasonal fashion. Incorporate these pieces into your wardrobe and enjoy a fall filled with elegance and style. Ready to update your wardrobe? Click now on GoodAndBad for more fashion inspiration and tips!

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