40 Best Old Money Winter Outfits For Women
Are you looking for old money winter outfits?
When I moved back to Ireland after spending years in the hot and humid climate of Malaysia, I had to figure out how to dress warm and still feel at my best.
I wanted to find comfortable and practical outfits that didn’t make me look like I bought everything from Decathlon.
If you’re looking for a way to dress with the subtle, yet chic old-money look without having to overthink it every morning, you’re at the right place.
We’re about to switch that old hiking parka (yes, it’s practical…) for carefully curated items that will make you look chic without breaking the bank.
Let’s take a look at the best old money winter outfits to nail the winter chic look this season with real pieces you can buy now!
Best Old Money Winter Outfits for Women
Here is a list of the best items to mix and match for the perfect old-money winter outfit.
1.Long Line Coat
A long line coat instantly pulls your whole outfit together and makes you look effortlessly polished. It’s the kind of winter piece that whispers “old money” without even trying.
- Here you can shop for my favorite long-line coat.
2.Leather Trench
A leather trench adds that sleek, confident edge while still keeping things classic. It’s bold, timeless, and makes even jeans look expensive.
- Here you can shop for my favorite leather trench.
3.Cashmere Turtleneck
A cashmere turtleneck feels like a warm hug and looks impossibly chic at the same time. Pair it with anything and it just elevates your whole vibe.
- Here you can shop for this pure cashmere turtleneck.
4.Cashmere sweater
Soft, breathable, and quietly luxurious, a cashmere sweater is the heart of every old money winter wardrobe. It’s simple, but it always looks high-end.
- Here you can shop for this cozy cashmere sweater.
5.Wool Coat
A tailored wool coat gives you structure and warmth without sacrificing elegance. It’s the kind of piece that makes every winter outfit feel intentional.
- Here you can shop for this beautiful wool coat.
6.Giant Scarf
A giant scarf turns even the simplest outfit into something rich and cozy. It’s practical, plush, and totally timeless. One of the easiest winter upgrades, honestly.
- Here you can shop for this giant scarf.
7.Leather Boots
Classic leather boots add polish to everything from dresses to denim. They’re durable, sleek, and feel like an instant style upgrade, whether it’s chic Chelsea boots or high-knee boots.
- Here you can shop for my favorite Chelsea leather boots.
8.Knit Midi Dress
A knit long winter dress is the perfect warm and cozy piece that, paired with the right accessories, will make you look super chic! It’s the perfect blend of feminine and minimal.
- Here you can shop for my favorite long winter dress.
9.Silk Blouse
A silk blouse brings that soft, elegant drape that instantly looks expensive. It’s effortless glam you can wear from day to night.
- Here you can shop for this affordable silk blouse.
10.Tailored Pants
Tailored pants make your whole outfit feel structured and intentional. They’re clean, crisp, and deliver that quiet luxury look with zero effort.
- Here you can shop for my favorite tailored pants.
11.Trending Sneakers
A pair of trending sneakers keeps your look modern while staying comfortable. They add that youthful, relaxed contrast to classic winter pieces.
- Here you can shop for the perfect modern and trendy sneakers.
12.Luxurious Riding Boots
These boots have that rich, deep leather tone that screams old money elegance. They’re sturdy, timeless, and pair beautifully with everything.
- Here you can shop for my favorite riding boots.
13.Mom Jeans
Mom jeans bring a relaxed, vintage feel that still looks put-together. They’re comfy, classic, and perfect for balancing dressier winter layers. Plus, it’s a timeless piece for every season!
- Here you can shop for the timeless mom jeans.
14.Knee-High Boots
Knee-high boots instantly make any outfit look sleek and powerful. They elongate your legs and add a luxurious touch to winter dressing.
- Here you can shop for these affordable knee-high boots.
15.Large Leather Tote Bag
A structured leather tote is both practical and polished — the perfect everyday luxury. It carries everything you need while keeping your look sophisticated.
- Here you can shop for this sleek leather tote.
16.Faux-Fur Coat
A faux-fur coat brings warm, plush glamour to even the coldest days. It’s dramatic in the best way and instantly feels old-school elegant.
- Here you can shop for this stunning faux-fur coat.
17.Oversized Blazer
An oversized blazer gives you that relaxed, effortless confidence. Throw it over any winter outfit and it instantly looks curated.
- Here you can shop for my favorite oversized blazer.
18.Leather T-Strap Loafers
These loafers offer a vintage prep vibe that never goes out of style. They’re refined, comfortable, and perfect for winter days when you want something sleek but easy.
- Here you can shop for these gorgeous t-straps loafers.
19.Midi Knit Skirt
A knit midi skirt adds soft texture and a feminine silhouette to your winter looks. It’s cozy, flattering, and incredibly versatile.
- Here you can shop for my favorite midi knit skirt.
20.Button-Up Shirt
A button-up shirt is the foundation of every polished wardrobe. Layer it under sweaters or blazers for instant old-money charm, the perfect timeless piece for your winter looks.
- Here you can shop for this timeless oversized button-up shirt.
21.Double-Breasted Coat
A double-breasted cut adds a special touch to your outfit. It’s classic, confident, and always looks good.
- Here you can shop for this affordable and chic double-breasted coat.
22.Cashmere Rollneck
A cashmere rollneck feels insanely comfortable and looks quietly luxurious. It’s a winter go-to that always works.
- Here you can shop for my favorite cashmere rollneck.
23.Leather Gloves
Certainly one of the easiest upgrades to your winter wardrobe, leather gloves are perfect for keeping you warm and making you look chic!
- Here you can shop for these beautiful leather gloves.
The Essence Of Old Money Winter Outfits
The essence of the old money look lies in the choice of material you wear, such as :
- Leather
- Wool
- Cashmere
- Silk
Pick earthy, warm, autumn tones for your wardrobe:
- Camel, maroon, chocolate brown
- Cream, beige
- Navy, dark green, charcoal, dark grey
Think minimal, timeless accessories that feel luxurious without being flashy.
Voilà! The Perfect Old Money Winter Outfits
There’s something about a carefully curated item, such as a warm knitted sweater or the perfect coat, that makes it effortless to wear a luxury look. Now you have everything you need to bring together the best old-money winter outfits without overthinking it.
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