Old money style is all about timeless, refined looks with a touch of effortless sophistication. I love how it embraces classic cuts, quality materials, and neutral tones that stay stylish year after year, not just for one season. This style is all about understated luxury and investing in pieces that last, which feels perfect for winter when we want outfits that are cozy but still polished. So, today, I’m excited to share 30 old money winter outfits that bring classic elegance to your wardrobe. Whether you’re already into this look or just discovering it, these outfits show how beautiful and sophisticated winter dressing can be.
30 Old Money Winter Outfits
1. Classic Camel Coat with Turtleneck and Trousers
Nothing says “old money winter” like a well-tailored camel coat paired with a neutral turtleneck and high-waisted trousers. Camel coats are a staple of old money fashion because of their neutral tones and versatile styling options. This outfit embodies timeless elegance and can be dressed up or down, making it perfect for both work and casual settings. Also, for an added touch, accessorize with a leather tote and loafers (find some classic options here).
2. Cashmere Sweater and Wool Skirt Combo
A cashmere sweater with a wool skirt is a cozy winter outfit that feels incredibly luxurious yet approachable. The high-quality materials offer warmth and durability, perfect for the colder months. Opt for neutral colors like beige, cream, or grey to embrace the classic old money winter aesthetic. Finish the look with knee-high boots and a structured handbag to tie it all together.
3. Oversized Blazer with sweater and Wide-Leg Pants
For a tailored yet relaxed look, an oversized blazer with a sleek turtleneck sweater and wide-leg pants checks all the boxes. Blazers add structure and an element of timeless elegance, particularly when they feature classic cuts and high-quality materials. This winter wardrobe staple can transition effortlessly from office settings to weekend gatherings. Pair it with loafers or ankle boots to complete the look.
4. Cashmere Scarf and Trench Coat Ensemble
A trench coat is one of the most iconic items in old money fashion, and when paired with a cashmere scarf, it becomes the ultimate winter outfit. This combination gives off a subtle luxury that feels not only fresh but also vintage, ideal for an old money aesthetic. Wear it over a wool sweater and trousers, and add loafers or leather boots. The neutral tones of this outfit overall make it a versatile addition to any wardrobe.
5. Peacoat with Jeans and Cashmere Sweater
A peacoat is a traditional piece that fits beautifully into an old money winter wardrobe. When paired with a cashmere sweater and dark-wash jeans, it achieves a relaxed yet polished look. This outfit is ideal for casual winter days and is a wonderful example of classic cuts meeting modern fashion trends. Accessorize with ankle boots and a simple leather handbag for a sophisticated edge.
6. Knitted Dress with Knee-High Boots
A knitted dress in a neutral tone embodies the soft, luxurious feel of old money winter outfits. Also, for an extra flattering look, cinch it at the waist with a leather belt. This is perfect for both daytime events and evening outings, and is easy to wear yet highly refined. Knee-high boots are a great way to complete the look, with your favorite handbag.
7. Scarf Jacket with Trousers
A scarf jacket paired with well-fitted trousers creates an effortlessly chic winter outfit. The high-quality coat provides warmth, while the trousers add a chic touch, balancing sophistication and comfort. For shoes, consider a classic pair of heels or ankle boots. This outfit is overall great for transitioning from professional settings to more relaxed occasions.
8. Slip skirt and sweater outfit
For those who love skirts even in winter, a slip skirt combined with a sweater is the ultimate cozy-meets-sophisticated choice. Opt for a skirt in neutral tones like taupe or ivory, and layer with a wool or cashmere sweater to add texture and warmth. Finish off your look with chic ankle boots or knee-high boots, making it perfect for winter outings.
9. blue Jeans, a cozy sweater and a structured blazer
Blue jeans, a cozy sweater, and a structured blazer make the perfect old money winter outfit. The jeans keep it classic and relaxed, while the sweater adds warmth and comfort. Topping it off with a structured blazer brings a refined touch, balancing cozy with sophistication for an effortlessly chic look that feels timeless and elevated.
10. Brown long coat with trousers
Classic long brown coats are timeless pieces that add structure and a sense of old money to any outfit. Pair one with jeans and loafers for an effortlessly polished, casual winter outfit. This look, while relaxed, keeps within the old money aesthetic with classic cuts and high-quality fabrics. Be sure to acessorize with a silk scarf and structured handbag to bring the look together.
Build Your Winter Wardrobe in the Old Money Style
Each of these outfits combines the key elements of old money style, including neutral tones, classic cuts, and high-quality materials. This makes them timeless additions to any winter wardrobe. Also for more casual old money style inspiration, you can check out this guide, or explore ideas for casual winter outfits to mix and match pieces. These pieces are more than just a fashion trend. They also represent a way of dressing that truly stands the test of time.
When curating an old money winter wardrobe, focus on pieces that you’ll love for years, knowing they’ll offer both style and substance in every season. By investing in these timeless essentials, you’re not only enhancing your look but also embracing the elegance of old money fashion that never goes out of style.
Shop Casual Old Money Style Winter Wardrobe Essentials
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Also, for more style inspiration, be sure to check out my most recent posts!
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Please feel free to email me at thegraydetails@gmail.com if you have any questions! I’m always happy to help with styling or picking out a specific outfit for an event! Have an amazing day!!
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