I’ve always thought shoes tell you the most about someone. Not in a judgmental way, but more in a “peek behind the curtain” sense. A pair of well-kept loafers usually belongs to someone who appreciates tradition. Ballet flats that have softened and shaped to the foot suggest years of wear, maybe even a story or two behind them.
When I think about old money shoes, logos or trends never come to mind. I think about the pairs that stick around.
The ones taken to the cobbler again and again. The ones your mother pulls from her closet and says, “Try these, you’ll see why they matter.”
Quiet luxury really shows in shoes. In leather that softens instead of cracks, in shapes that still look right years later, in shades of brown, navy, or black that quietly work with anything you put on.
You can swap out sweaters or rotate coats, but old money shoes? They are more revealing. They need to be chosen carefully, worn often, and taken care of if they are going to tell a good story.
Here are ten old money shoes that truly embody the idea of quiet luxury.
1. The classic penny loafer
If one shoe captures old money style, it’s the loafer. The penny version especially feels like the foundation of a good wardrobe. Neat, polished enough to look intentional, but never flashy. My first pair wasn’t new at all, I found them in a consignment shop and wore them nearly every day through grad school. They somehow worked with everything: jeans, wool skirts, even the trousers I pulled out when I wanted to look like I had my life together.
What I love about loafers is how universal they are. You see them in Ivy League libraries, on Paris sidewalks, and with sharp tailoring in Milan. Bass Weejuns are a reliable entry point, but Aeyde and Gucci loafers feel like true investments. If you keep them polished, they can last for decades, and in fact, they get better with age.
2. Tall riding boots
Every fall, I dig out my riding boots and remember why they’ve stayed with me. There’s something about knee-high leather that instantly feels refined. No extra buckles or shiny details, just smooth leather, a low heel, and that slight equestrian edge.
I like brown for a softer, everyday feel and black when I want something cleaner. Most of the time I wear mine over slim trousers, but they look just as right with a skirt and a heavy coat. They manage to feel at home in the city but would not look out of place in the countryside either, which is probably why I keep going back to them year after year.
3. Ballet flats
I once thought ballet flats were too plain. Then I started noticing how French women wear them, never flimsy, always with a bit of structure, and sometimes with the smallest bow that feels more like a detail than decoration. Chanel made them iconic, of course, but Repetto and Margaux make versions that feel just as polished without being overly precious.
I rotate between navy and nude, depending on the season. They are the pair I slip into when sneakers feel too casual but heels are too much. I wore a black pair through Rome one spring and never once felt underdressed, even at dinner. That is the magic of a truly timeless flat.
4. Suede driving moccasins
Driving moccasins are not flashy. They are understated to the point of invisibility, which is precisely the charm. Tod’s has been the leader with their pebble sole, but other Italian brands do it beautifully as well.
I think of them as the kind of shoes you grab on a Saturday morning. Easy to wear to the market, or for a slow drive with the windows down. They’re soft and easy, never fussy. Worn with chinos or slim trousers, they have that worn-in feel that only comes after years, not just a season.
Other option: Aeyde
5. Polished leather oxfords
Slip into oxfords and you instantly feel sharper. They remind me of old libraries and coats that hang heavy with cashmere. On women, I especially love how they bring a touch of masculine energy to a softer outfit. Ankle-length trousers, a crisp shirt, maybe a cardigan, and suddenly the outfit feels quietly intentional.
Oxfords demand care, but in return they age beautifully. A quick polish every now and then, and they last for years. They’re never showy, yet somehow they always look right. It’s worth it.
6. Simple ankle boots
Ankle boots are the pair you end up living in. Low heel, comfortable, usually in suede or leather. They’re not there to steal attention, just to make getting dressed simpler.
I’ve worn the same camel suede pair winter after winter. They go with jeans, heavy coats, even dresses, as long as the design stays simple. The plainer the boot, the more often you’ll wear it.
7. Canvas tennis shoes
Even sneakers can lean old money when they’re simple. A pair of white Superga, slim Keds, or plain Converse will do the job. Nothing flashy. Just canvas, laces, and a clean rubber sole.
I keep a pair by the back door for quick errands, but they often find their way into travel outfits as well. I wore my Superga on a trip to Florence and they were perfect for long walks across uneven streets. They made my outfits look casual but never sloppy. That is what makes them timeless.
8. Leather slingbacks
There is something graceful about a slingback. The strap feels lighter, and with a mid-heel you can actually wear them all day without thinking about it. Chanel’s two-tone version is the classic, but I’ve found lovely pairs at Reiss and Massimo Dutti that feel just as polished.
Slingbacks are the shoe that tells people you thought about your outfit without overthinking it. I wore a nude pair to a friend’s garden wedding, and they looked just as right on the grass as they did at the reception dinner.
9. Boat shoes
Boat shoes can tip into preppy territory if you overdo them, but kept simple they have an easy kind of elegance. Sperry has been the go-to for decades, though Italian makers often give the shape a slightly sleeker look.
They remind me of summers by the water. Linen shorts, striped sweaters, hours spent outside. The only rule is to keep them neat. Polished leather and properly tied laces are what keep them in the old money category. Worn down and messy, they lose the effect entirely.
10. Elegant evening pumps
A wardrobe is not complete without one pair of evening pumps. Nothing too high or sparkly, just a sleek mid-heel in suede or leather. Pointed or almond toe, in black, navy, or nude.
I’ve had a pair of black suede pumps for years, worn everywhere from weddings to work dinners. They never feel out of place, quiet, reliable, and are exactly what old money style is about.
How to keep them alive
Old money shoes are not about owning dozens of pairs. It comes down to choosing well and looking after them. My loafers are over ten years old and still get noticed, mostly because I’ve kept them polished and had them resoled instead of giving up on them.
Simple habits make all the difference: cedar trees to hold their shape, the cobbler for fixes, a touch of conditioner now and then. Look after them and they’ll stay with you for years.
Where to begin
If you’re starting fresh, begin with three: loafers, ballet flats, and ankle boots.
Riding boots make sense if winters are cold, slingbacks if you go to events, and pumps cover formal occasions.
Moccasins and boat old money shoes are nice extras if they fit your lifestyle.
The goal is not abundance, but consistency. Old money shoes belong to a wardrobe where everything has been chosen thoughtfully. Fabrics matter more. Accessories begin to carry meaning. Even the way you store them changes.
And when you start thinking about your closet this way, it shifts everything.
