These Timeless Loafers Are $600 — And Worth Every Penny

When you work at Wirecutter, a healthy dose of price-tag skepticism is a prerequisite. But as the senior style editor, I also know that when shoes cause you to audibly gasp, they’re worth way more than the cost of the leather and glue.

It may sound like a scam, but I’ve perfected an incredibly simple method to spend dramatically less on my wardrobe without any sketchy hijinks. Here’s my secret: I pay more.

I pay up for the high-quality, long-lasting item that’s exactly what I want. Not a dupe, not something I pick up because it’s on sale. Instead I pay the full retail price of the thing I know I will wear into the ground. And I end up spending less because I buy far less. When I gasp with glee at a pricey pair of shoes, I buy them. Otherwise, I don’t.

That’s how Jamie Haller got 595 of my dollars, and I got a perfect pair of her slipper-like penny loafers. It was more than a fair trade.

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With these pricey loafers, you actually get what you pay for. For one thing, they’re gorgeous — in the least-flashy way possible. And they’re handmade with gleaming, super-soft leather that comfortably encases your feet.

So often I see designers trying to find unique ways to reimagine classic pieces — possibly to try to sell you a slightly different version of something you already own. The problem is this: The thing that makes their version “special” is also what makes it feel dated in a couple of years. It can give you the illusion you’re “investing” in something that you don’t actually end up wanting to keep long-term.

That’s not the case with these loafers, which, for me, achieve legit investment status. Something with a classic, no-frills silhouette made from gorgeous, high-end materials will never look wrong, even when trends change.

Like I do, Jamie Haller lives and works in Los Angeles. So several years ago, when I was introduced to her laidback luxe shoes by one of my in-the-know fashion friends, I felt like I’d found a designer who understood exactly how I wanted to dress.

The brand now includes a large collection of shoes and clothing, and I still find that practically everything she makes works perfectly for my casual city wardrobe. The designs are elevated, but they don’t feel stuffy, and the relaxed silhouettes are perfect to wear every day. And I do mean every single day. On a recent trip to Wirecutter headquarters in New York City, I packed two pairs of shoes for my four-day stay, yet I wore just one pair: my JH loafers. They work equally well with baggy jeans and a T-shirt on a travel day and a midi skirt and blazer for a night out.

My first JH pair was in the oxblood color, a highly coveted and often-sold-out brownish-red (shown above) that’s more neutral than you might expect. Now there are about a dozen subtle, gorgeous colors and textures, including suede, croc, and ponyhair. Certain colors sell out fast, but if you sign up for the email list, the company sends out a heads-up prior to restocking.

Wearing most loafers — even those we recommend — can feel like a badge of honor. That’s because many use stiff inserts, called counters, to provide structure and shape. It can take weeks or months of pinching and blisters to earn some comfort.

This pair is perfect from day one. The design is gorgeously simple, and it highlights the leather and expert construction. The rounded silhouette is delicate yet doesn’t pinch or crunch the toes. The leather outsole is thin and pliant, so the shoe flexes with every step. My very first JH loafers were a little slippery to walk in. But in recent years the brand has solved this by updating the design to include an inset rubber pad at the ball of the foot, for better traction.

If you follow Jamie Haller on Instagram, which I obviously do, you can watch her travel to Italy to source leather and gab with the artisans who are handmaking these shoes. Each pair is made with Italian Bufalini leather, using traditional sacchetto construction. That means the artisans stitch the shoe’s lining and insole together to form a sacchetto (or “little bag”) before attaching the upper. This prevents any seams inside the shoe that might cause rubbing. The result is a smooth glide into the loafer and an insole that truly does mold to the shape of your foot.

Jamie Haller’s loafers are soft fresh out of the box, but they have enough heft to still feel supportive. The brand describes them as having a glove-like fit. But since I’ve never liked the feeling of wearing gloves, I think of the fit more like wearing your favorite, well-loved bedroom slippers — just about a million times more chic.

If you need shoes with arch support, you should plan to make some adjustments. The interior is lined with super-smooth leather, and the footbed has thin padding, but the sole is almost completely flat. If you want to add an insert, I’d recommend sizing up a touch to provide some extra room. If you wear these loafers au natural, they fit true to size.

My oxblood pair is now three years old, and I think they look better than the day I opened the box. They’re worn in and creased — clearly loved. But the leather has only gotten softer and more beautiful as the patina has developed. The rubber heel is wearing a bit thin — I’m probably due for a visit to my cobbler for a replacement. And I’ll happily put in the maintenance because, if I’m lucky, I’ll be wearing these shoes for the next decade.

This article was edited by Maxine Builder and Catherine Kast.