You know that person who walks in and just has it? Like, they’re not even trying, but everyone notices them? Nine times out of ten, it’s the shoes.
I’ve been thinking about this lately—especially after spotting a woman at a tiny café in Charleston. She had on beat-up leather loafers, a silk scarf, and the most perfect navy trench. Nothing fancy. But it all looked effortless and classic. Like she didn’t Google it—she just had it.
That’s the power of old money loafers.
What Are Old Money Loafers?
There’s nothing fussy about them. Just good, solid shoes in buttery leather or soft suede. Black, brown, maybe burgundy if you’re feeling bold. No logos. No fuss. The kind of shoes that work with everything but never scream for attention.
My grandmother had a pair she wore with everything—from linen pants to her Sunday dress. And honestly, they’d still look perfect today with your favorite jeans or a trench coat on a rainy morning.
A Quick History Lesson
Loafers started as comfy slip-ons in Norway (seriously!), and then became the go-to for Ivy League students in the ’30s. After that, it was all over—Grace Kelly, Audrey Hepburn, and basically every well-dressed European started wearing them.
They’re the kind of item that doesn’t need to change much because they were made right the first time.
Why They Still Work in 2025
Loafers aren’t trying to be trendy—and that’s exactly why they’re still everywhere. They’ve outlasted platforms, pointy stilettos, even those stretchy sock-sneakers that were big for a minute.
What I love about them is how easy they are. You don’t have to overthink it. You can pair them with jeans and a T-shirt or throw them on with a skirt and sweater. They somehow make it all look pulled together, even if you’re running late or forgot to brush your hair (been there).
And they’re comfy! Like actually wearable for more than an hour. No rubbing, no weird balancing act. Just slip them on and go.
The Best Old Money Loafers to Buy Right Now
Here are five pairs that balance quality and price—and will keep you looking timeless for years:
1. Everlane The Modern Loafer
These are sleek without being stiff. The leather is soft enough to break in fast, and the colors are classics: think black, bone, and rich cognac. They’re perfect for work, but casual enough for weekends. You’ll wear them way more than you expect. They have a slightly pointed toe, which makes your whole outfit feel a little sharper—without being uncomfortable.
[Link to Everlane Loafer]
2. Margaux The Penny Loafer
These look straight out of a Nancy Meyers film. They’re beautifully made with padded insoles, come in extended widths, and have that just-polished-enough vibe. They feel grown-up in the best way—like you’re ready to run a meeting or pop into a bookshop. What’s nice is they mold to your feet over time, so they feel more like “your” shoes every time you wear them.
[Link to Margaux Penny Loafer]
3. Sam Edelman Loraine Loafer
These are a Pinterest favorite for a reason. They’re soft, flexible, and look way more expensive than they are. The gold hardware is a nice touch that feels designer-y without being loud. A great everyday pick, especially if you want something dressy-ish but comfy. I’ve worn them to dinner and on long walks downtown—they somehow work for both.
[Link to Sam Edelman Loraine]
4. Rothy’s The Loafer
Lightweight, washable, and eco-friendly? Yes, please. These are perfect for travel or long days on your feet. They’re knit (not leather), so they have a more relaxed vibe but still manage to look tidy. Great if you live in a rainy climate or are always on the go. Plus, they’re made from recycled water bottles, which is pretty cool.
[Link to Rothy’s Loafer]
5. G.H. Bass Weejuns
The original penny loafers. These have been around for decades—and for good reason. They’re sturdy, classic, and come in lots of colors and finishes. Expect a little break-in period, but after that, they’re the loafers you’ll wear forever. Think East Coast prep, in the best way. I’ve even seen them styled with slouchy socks and dresses, and it just works.
[Link to G.H. Bass Weejuns]
How to Style Them (Without Looking Too Preppy)
Here are a few outfit ideas that feel classic but still relaxed:
With Jeans and a Sweater
The easiest combo. Throw on a slouchy knit, straight jeans, and your loafers. Done. Add a messy bun and crossbody bag if you’re heading out.
With Wide-Leg Trousers and a Blazer
Makes you look like you’ve got your life together—even if your inbox says otherwise. Add a plain white tee underneath to keep it chill.
With a Midi Dress and Socks
It gives vintage charm. Try a neutral sock and a trench coat for extra style points. This combo is especially cute for early spring and fall.
With Shorts and a Button-Down
An easy warm-weather outfit. Add some sunglasses and you’re golden. Try tucking in one side of the shirt for that “I just threw this on” vibe.
Tips for That “Old Money” Feel
- Go for natural fabrics: cotton, linen, wool.
- Stick to calm, classic tones—navy, cream, camel, soft green.
- Add quiet details: a leather crossbody, a pearl stud, or a silk scarf.
- Keep everything neat but never too perfect. The goal is lived-in elegance.
Oh, and let your loafers get a little worn in. A few creases or scuffs only make them look better.
People Also Ask
Are loafers still in style in 2025?
Definitely. They’ve stuck around for decades and only keep getting better. They’re a reliable choice when you want to look put-together without trying too hard.
What color loafers are the most versatile?
Black and brown are safe bets. Burgundy is a fun, still-classic twist that adds warmth. Cream or bone shades are great for spring and summer.
Can I wear loafers without socks?
Yes—just grab a good pair of no-show socks so your feet stay comfy. Or, if you’re into the look, show your socks! A ribbed cotton sock can be a fun touch.
Are loafers good for wide feet?
Yes! Brands like Margaux and Naturalizer have roomy, stylish options. You can also try breaking in a classic leather pair with thick socks at home.
Final Thoughts
Loafers aren’t the flashy pair you post on Instagram. They’re the ones you reach for again and again without thinking. They just work. Like a great white shirt or your favorite mug—the one with the chipped handle but perfect feel.
They’ve seen work meetings, coffee runs, long flights, and lazy Sundays. And each time, they make you feel just a bit more like yourself.
Whether you go with shiny black leather or soft tan suede, your loafers will only get better with age—just like a great playlist or your favorite pair of jeans.
And once you start wearing them, don’t be surprised if you start skipping the heels more often.
