As the leaves start to change and the air turns crisp, fall brings with it a sense of renewed elegance. In a world where fast fashion dominates, the “Old Money” aesthetic offers a breath of fresh air, capturing timeless style, understated luxury, and a sense of refinement that transcends trends. For fall 2024, this look is stronger than ever, blending the charm of vintage with modern-day sophistication. It’s all about quality over quantity, investment pieces over fleeting fashion, and neutral tones that exude quiet confidence. More than that, it’s about the assurance that comes from wearing pieces that not only look beautiful but also feel like they could be handed down through generations.
But what exactly is Old Money fashion?
The Old Money style embodies timeless elegance, focusing on quality and simplicity over fleeting trends. Rooted in neutral tones, impeccable tailoring, and luxurious fabrics like cashmere and silk, this aesthetic is effortlessly chic. Think tailored coats, crisp shirts, and refined accessories like structured handbags and silk scarves. To help you channel this understated sophistication, I’ve curated over 25 fall outfit ideas that perfectly capture the Old Money vibe. Let’s explore how to build a wardrobe that exudes class and timeless luxury this season.
If you’re ready to build a fall wardrobe that exudes timeless sophistication and luxury, let’s dive into these carefully curated Old Money fall outfit ideas.
Tailored Wool Coat + Silk Scarf
A wool coat is a true investment piece that never goes out of style. Opt for a long, structured wool coat in neutral colors like camel, grey, or navy. Pair it with a silk scarf for a pop of luxury. This look is perfect for chilly autumn days when you need to stay warm but still want to look polished. Add a classic leather handbag and low-heeled ankle boots to complete this elegant, Old Money ensemble.
Cashmere Sweater + Pleated Midi Skirt
A cashmere sweater offers unmatched softness and warmth. Choose a crewneck or turtleneck in a neutral tone like cream, grey, or beige. Pair it with a pleated midi skirt in a rich, autumnal hue—think forest green or burgundy. This look is sophisticated yet feminine, and it can easily transition from office to dinner out. Add loafers or ballet flats to keep the look refined and comfortable.
Tweed Blazer + High-Waisted Trousers
Tweed has long been associated with the Old Money aesthetic, thanks to its connection to traditional British and French fashion houses. A tailored tweed blazer in houndstooth or plaid exudes vintage charm. Pair it with high-waisted trousers in a coordinating neutral color for a balanced, put-together look. Wear this with a simple silk blouse and leather loafers to finish the outfit with subtle elegance.
Button-Up Shirt + Wool Slacks
The crisp white button-up shirt is a wardrobe staple that embodies simplicity and elegance. Pair it with wool slacks in shades like taupe, charcoal, or navy. This look is timeless and perfect for an office setting or a more formal gathering. Tuck in the shirt and add a leather belt to define the waist, while pointed-toe flats or loafers keep it sleek and minimal.
Trench Coat + Ankle Boots
A classic beige trench coat is a must-have for any Old Money-inspired wardrobe. The clean lines and structured fit create an instantly polished look. Pair it with sleek black ankle boots to create an outfit that’s ideal for fall. Layer it over dresses, trousers, or skirts for versatility. Opt for minimal jewelry like gold hoops to keep the look simple but elegant.
Crew Neck Sweater + Plaid Skirt
A crew neck sweater paired with a plaid skirt creates a preppy, collegiate-inspired look. The sweater should be in a soft, neutral color to balance the boldness of the plaid. This combination works well for casual days at the office or weekend brunches. Add knee-high socks or tights and finish the look with loafers or ankle boots to keep it practical yet stylish.
Classic Black Dress + Pearl Accessories
The little black dress is a timeless classic. Choose a sleek, tailored black dress that hits just below the knee for a sophisticated touch. Pearl earrings and a matching necklace elevate the outfit, adding an air of Old Hollywood glamour. Pair with classic pumps or slingback heels to complete the look, which is ideal for evening events or formal dinners.
Cable Knit Sweater + Riding Pants
A cozy cable knit sweater in ivory or cream can be dressed up when paired with tailored riding pants. This outfit is perfect for a day at the stables or a leisurely autumn walk. Riding boots and a structured handbag complement the equestrian-inspired look, adding sophistication and ease.
Camel Turtleneck + Plaid Trousers
A camel turtleneck sweater offers warmth while looking effortlessly chic. Pair it with high-waisted plaid trousers for a smart and cozy fall outfit. Opt for leather loafers or boots to keep the look grounded in classic sophistication, and add a statement belt for a touch of personality.
Oversized Blazer + Straight-Leg Jeans
An oversized blazer in a neutral tone instantly elevates a casual pair of jeans. Choose straight-leg jeans in a dark wash for a more polished look, and add a simple white blouse underneath. This is a versatile outfit that works for both casual Fridays at the office or weekend outings. Complete the look with loafers or pointed flats and a leather crossbody bag.
Double-Breasted Coat + Silk Blouse
A double-breasted coat in a luxurious fabric like wool is a quintessential fall staple. Wear it over a delicate silk blouse in soft shades like ivory or blush for a refined, feminine look. This outfit works well for both day and evening events. Add tailored trousers or a midi skirt and complete the look with heeled ankle boots or loafers.
Loafers + Tailored Cigarette Pants
Loafers are a key footwear choice for the Old Money aesthetic. Pair leather loafers with tailored cigarette pants for a sleek and comfortable look. Choose neutral colors like navy, grey, or beige, and add a fitted sweater or button-up shirt. This ensemble is perfect for both office wear and casual settings where you want to look effortlessly polished.
Black and White Old Money Ensemble
The black-and-white color scheme is an iconic part of the Old Money aesthetic. Pair a crisp white blouse with tailored black trousers or a sleek pencil skirt for a timeless, monochromatic look. Add a fitted black blazer for extra polish. Keep accessories minimal—black leather loafers, a classic wristwatch, and a structured bag will complete this high-society-inspired outfit.
Tailored Suit + Turtleneck
A tailored suit in a classic color like charcoal, navy, or black is a must-have for fall. For a modern twist, layer it with a slim-fitting turtleneck in neutral tones like cream or beige. This outfit strikes the perfect balance between professional and stylish. Finish the look with loafers or pointed-toe heels for a sophisticated touch.
White Cable Knit Sweater + Pleated Mini Skirt
A white cable knit sweater paired with a pleated mini skirt offers a youthful yet classic look. The skirt can be in neutral shades like grey or plaid for a preppy touch. Add opaque tights and loafers or ankle boots for a complete fall-ready outfit that’s comfortable yet polished.
Trench Coat + Wide-Leg Pants
For a dramatic and elegant silhouette, pair a long trench coat with wide-leg pants in coordinating shades like beige or navy. This look is effortless and chic, perfect for fall days when you want to stay warm without compromising on style. A pair of heeled ankle boots adds sophistication and height to the ensemble.
Knit Dress + Knee-High Boots
A knit dress offers both comfort and style. Choose a ribbed or cable-knit dress in a muted tone like taupe or grey. Knee-high boots in leather or suede complete this look, making it perfect for a day out shopping or a casual dinner. Add a long wool coat for extra warmth.
Polo Shirt + A-Line Skirt
A fitted polo shirt paired with an A-line skirt is an equestrian-inspired outfit that exudes Old Money charm. Stick to neutral colors like navy, cream, or black, and add leather accessories like a belt or boots to complete the preppy, polished look.
Houndstooth Coat + Chunky Knit Scarf
Houndstooth is a classic pattern associated with traditional luxury. Choose a long houndstooth coat and layer it with a chunky knit scarf in a contrasting color. This combination adds texture and warmth to your fall look, perfect for colder days. Pair with fitted pants and ankle boots for an effortlessly chic outfit.
Cashmere Turtleneck + Pleated Trousers
A cashmere turtleneck in a neutral tone is an essential layering piece for fall. Pair it with pleated trousers in a complementary shade for a smart, comfortable outfit. Complete the look with loafers or ankle boots and minimal gold jewelry for a touch of understated elegance.
Long Wool Cardigan + Silk Cami
A long wool cardigan in a neutral color like grey or beige can be layered over a silk camisole for a soft, luxurious look. Pair with tailored trousers or jeans for a balanced mix of casual and elegant. Add loafers or ballet flats to keep the look classic and relaxed.
Silk Slip Dress + Wool Overcoat
A silk slip dress can be made fall-appropriate by layering it under a wool overcoat in rich, autumnal shades like deep green or burgundy. This combination of soft silk and structured wool adds both warmth and texture. Pair with ankle boots or loafers for a chic and cozy fall outfit.
Blouse with Puff Sleeves + High-Waisted Wool Pants
For a more feminine take on the Old Money style, try a blouse with puff sleeves in a delicate fabric like silk or chiffon. Pair it with high-waisted wool pants for a balanced look that’s both modern and vintage-inspired. Finish the outfit with ballet flats or loafers.
Shearling Coat + Skinny Jeans
A shearling coat adds a touch of warmth and texture to your fall wardrobe. Pair it with fitted skinny jeans and ankle boots for a cozy yet stylish look. This outfit is perfect for a day out in the city or a casual weekend gathering.
Navy Blazer + Silk Turtleneck
A tailored navy blazer paired with a silk turtleneck creates a polished, professional look. This outfit works for both office wear and smart casual settings. Pair with tailored trousers or straight-leg jeans and finish with loafers or ankle boots for a chic, fall-ready ensemble.
Faux Fur Vest + Flared Jeans
A faux fur vest in a rich shade like deep brown or burgundy can elevate a simple pair of flared jeans. This combination creates a retro-inspired look that still feels modern and luxurious. Add a fitted turtleneck and pointed-toe boots to complete the outfit.
