Do you love the ‘old money’ vibe or look? I’m sharing which shoes to have in your wardrobe this fall and winter for that quiet luxury aesthetic, no matter your budget!
Fall & Winter Old Money Shoe Capsule Essentials
Does your style leans toward refined and timeless? You’ll be happy to know that fall and winter are the seasons to truly shine.
I love incorporating polished, understated pieces that feel effortless yet elevated into my fall and winter wardrobe, foorwear included! Shoes are really the foundation of an outfit and set the tone, whether you’re heading to the office, a holiday dinner, or simply strolling the city streets.
Ahead, I’ve curated a list of the top 6+ shoe styles that I believe belong in an elegant cold-weather capsule. Each one brings that whisper of quiet luxury that the old-money aesthetic is known for. And, I’ve included both investment and budget-friendly picks so you can build your capsule your way.
1. The Classic Loafer
Loafers whisper understated elegance. Slip them on for a crisp morning walk for coffee or pair them with a tailored coat for a business meeting or brunch with friends . They bring a refined touch to trousers, dark denim, or even a knit dress or skirt layered with tights. For fall and winter, I recommend timeless, luxe-looking colors like chocolate brown, sleek black, dark beige, or warm cognac.
- Luxury option: Gucci Horsebit Leather Loafers— these are the ultimate symbol of refined taste. I’ve had this pair for years and they’ve never fallen “out of fashion”, hence why they are such a timeless pair.
- Budget-friendly option: Quince Leather Loafers— this pair is elegant, sleek, and won’t break the bank, and they look so much like the Gucci Horsebit loafers, you’ll do a double take!
2. Elegant Ballet Flats
Next up, ballet flats carry an effortless grace that feels quietly posh. They are ideal for days when you want to look polished yet comfortable, whether running errands or meeting a friend for lunch. In the cooler months they pair beautifully with straight leg jeans, long pleated trousers, or a midi slip skirt layered with tights and a chunky sweater.
- Luxury option: Chanel Lambskin Ballerinas— the iconic old money ballet flat. I splurged on a secondhand pair of these several years ago and haven’t regretted it once! In my opinion, these shoes are worth every penny.
- Budget-friendly option: Quince Leather Flats— these classic ballet flats are beautifully crafted and Parisian-approved. They are another great lower-cost option but still have that Chanel look with the cap-toe detail. Not to mention, they are made of genuine leather and have such a classic vibe.
3. Suede Sneakers
In my opinion, suede sneakers strike the perfect balance between laid back and elevated. Not only is the suede texture very fall-forward, they pair effortlessly with wool coats, jeans, and trousers. I feel like they give that “sporty old money” vibe, where a cable-knit sweater layered over a striped button-down fits the bill.
- Luxury option: Tod’s Suede Slip-On Sneakers –these gorgeous suede brown sneakers have a sporty and elevated vibe, with a detail that makes them look like a loafer/sneaker hybrid, perfect old money combo. For a lower cost (but still investment) option, take a peek at the Tory Burch Phoenix Sneakers!
- Budget-friendly option: Quince Italian Suede Sneakers – Quince never ceases to amaze me with their luxury-for-less options. These suede sneakers are classic, elevated, and come in three beautiful shades for fall and winter (all under $70!).
4. Leather Slingback Heels
Low slingback heels are perfect when you want a touch of height without sacrificing comfort. They emanate grace, whether paired with a silk slip skirt or tailored trousers. For the fall and winter months, I recommend choosing a classic neutral tones like black, navy, or nude.
- Luxury option: Poppy Barley Claire Kitten Heel —subtle sophistication at its finest. These heels are perfect for date nights, business events, or holiday gatherings. (Use code “STYLEYOUROCCASION-25” for $25 off!)
- Budget-friendly option: Bianca Slingback Pump —sleek, simple, and affordable. I love the patent leather option with a little bit of shine.
5. Heeled Ankle Boots
Next on the list, a sleek ankle bootie will add a chic appeal to your fall and winter outfits without feeling too heavy. For that old money look, I recommend a soft cream or nude color (monochromatic or tonal outfits in the winter is key). You can wear these with midi skirts, jeans, or tailored trousers.
- Investment: Stuart Weitzman Vinnie Bootie – I absolutely love these boots for fall and winter seasons. The sleek style is elevated yet still versatile, not to mention they are known for their comfort level too!
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Budget-Friendly: Seychelles Leather Ankle Boot – At just under $75 these sleek ivory ankle boots are both budget-friendly and chic!
6. Chelsea Boots
Chelsea boots are a staple in any fall/winter wardrobe and can look old money with a sleek black, chocolate brown, or warm brown suede finish, and subtle heel. Bonus if they’re waterproof.
- Investment: Vagabond Mona Bootie in Brown Suede – These semi-affordable Chelsea boots are seriously chic. I adore the brown suede finish (which is waterproof!) and the low chunky heel. These would look so great with jeans, a knit dress, or under loose-fitting trousers.
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Budget-Friendly: Quince Suede Chelsea Boots – at just under $100, these suede boots are stylish and subtle. I love the cinnamon brown but they also come in light tan and black.
7. Tall Riding Boots
Tall riding boots are a cornerstone of the old money aesthetic. Rooted in equestrian tradition, they carry a polished charm associated with countryside estates and weekend escapes. So, it should be no surprise I included them on my list!
For fall and winter, they are both practical and elegant, keeping you warm while elevating everything from thick leggings and cashmere sweaters to midi skirts and tailored coats.
- Investment: SCAROSSO Lauren Boots – these sleek Italian leather riding boots have a classic knee-high cut, rounded toe, and low stacked heel. Timeless and versatile, they’ll add effortless polish to any fall or winter look, and I love the small buckle detail at the top!
- Budget-Friendly: Steve Madden Roberta Boots – at just over $100, these boots feature a tall, structured silhouette with a sleek finish and low heel. They also have a cute horsebit detail and can bring a chic, equestrian-inspired edge to everyday fall and winter outfits.
Below is a great way to style riding boots in the fall/winter. Don’t miss this article for more old money outfit inspiration!
I hope you loved this article and have found the inspiration you need to build your fall/winter shoe capsule with an old money vibe! Don’t miss The Art of Dressing Old Money in 2025!
