I Own 20 Pairs of Loafers. These Are the Ones Worth Buying.

While the pairs that follow are in no particular order, Weejuns are first on this list because they’re truly unmatched. (They are, after all, ourbest overall women’s loafer.) They have a flatteringly low profile and a perfectly balanced almond-toe shape — not too narrow, not too bulbous. The signature “whale tale” penny keeper adds a bit of interest but isn’t distracting. The heel is just under one inch, for a tiny bit of lift that can read either polished or casual. The same can be said of the upper, which, especially in its traditional semi-gloss box leather, is easy to dress up or down.James Deanwore them.Grace Kellywore them.Chloë Sevignywears (anddesigned) them. And I wear them, inblack,brown,wine,navybox leather, andolive suede. (I also have themary janes.) Weejuns look good on everyone and can be worn with just about anything.

I own so many pairs in part because they’re a timeless style but also because I haven’t needed to get rid of any: Weejuns (short for “Norwegians,” a nod to the penny loafer’s Norwegian roots) have been made the same way since their introduction in 1936, with a hand-sewnmoccasin-style constructionfor a comfortable socklike fit and a Blake-stitched leather outsole (the outsole is sewn to the insole, rather than simply glued to it) for incredible durability and flexibility. And while they’re technicallynotwaterproof, I do have a ten-year-old box-leather pair that’s spent many days trudging through soaking rain in both New York and London and is still going strong. To top it all off, they’re priced right, very easy to resole, and, despite their sturdiness, break in incredibly quickly.

All this is to say that if you buy just one pair of loafers, make it these. (They run big, so order a half-size down.)

Whata gorgeous pair of shoes. They look and feel amazing right out of the box and have the loveliest rich leather scent. The brand describes them as loafers “with the understated soul of a slipper,” but the slipper part is no way understated — the pliable leather outsole, waxed buffalo upper, and supersoft leather lining make my feet feel like they’re being taken care of (a quality I’ve never thought to apply to a shoe before), and I’m always reluctant to take them off at the end of the day.

These loafers aren’t cheap, and you can definitely find some amazing pairs for much less (the aforementioned Weejuns, for example), but the craftsmanship and quality justify the cost: In addition to using luxury materials, they’re also handmade in Italy with a traditionalsacchetoconstruction (the lining wraps up and around the foot and is stitched directly to the upper — you can watch an examplehere) for a conforming and cradling fit that eliminates the need for a more rigid insole. The process requires extra care and thus extra cost. It’s also a clear sign of a high-quality shoe.

This is exactly what comes to mind when I envision a classic prep-school penny loafer, especially in the caramel-yTan Labrador colorwith its contrasting white stitch (which is what I own). A pair of these would have looked perfect with the uniform kilts I wore through high school, and these days I like pairing them with a pair of straight-leg denim and a fisherman sweater for an appropriately Nantucket-y vibe.

Even though I haven’t been wearing them for long, I’m going out on a limb and declaring the Pinch Penny the most well-made, workhorse pair of loafers I’ve ever put on. The handsewn upper is made of thick, unlined, full-grain, hand-burnished cowhide. They have a moccasin-style construction, lightly padded insole, tacked heel, and Blake-stitched double-leather outsole that’s built to last for ages. (You can watch Rancourt & Co. make its similarly constructed Beefroll Loafers in painstaking detailhere.) Their high quality is immediately evident just by holding them and is pleasingly counterintuitive to their flexible fit that requires minimal break-in time. And they fit perfectly true to size.

I don’t often wear driving-moc-style shoes from any brand, but I do ownthis handmade-in-Italy M.Gemi pair, and I feel very confident recommending them. They’re a convincing dupe for a traditionalTod’s Gommino loafer— same overall profile and toe shape, moccasin-style construction, and deconstructed rubber nib (gommini)outsole — but at a fraction of the price. Their tumbled upper easily molds to the foot but still feels thick, sturdy, and built to last. The outsole, however, is a different story: The style was patented in 1963 by Car Shoe company founder Gianni Mostile and designed specifically for driving — the rubber nibs are perfect for gripping car pedals and are neither intended nor built to withstand long periods of walking. And, unlike traditional-heeled loafers, they’re basically impossible to resole to their original condition. The worn-out nibs would most likely be sanded down and replaced with a solid rubber or leather outsole, resulting in a more standard-looking moccasin.

Nonetheless, I personally don’t anticipate replacing this shoe, outsole or otherwise, for a number of years. Driving mocs have long been a symbol of luxury and sophistication, and those inherent qualities make me feel pulled together no matter what my nibs look like. In fact, my only quibble with these shoes is that they run just a tad too small — an issue I remedied with someliquid shoe stretcher, though you can also try going up a half-size.

Like every Rothy’s shoe I’ve tried on,The Penny Loaferis comfortable, machine-washable, and very well made. Very unfortunately, it’s just not for me — the overall shape is spot-on (flattering almond toe, no-nonsense penny-keeper strap, low profile outsole and heel), but the combo of athletic-adjacent knit upper and rubber outsole is approachingsnoaferterritory, and I’m not here for that. The heavier nap on theReVelvet versionis definitely a step in the right direction, but it’s still too sporty for my taste.

However, ifyoulike the look of these loafers (and there’s no objective reason you shouldn’t), they’re an absolute must-buy: I have a three-year-old pair ofthe Square Toe Mary Janesthat, given how I treat them, should be completely destroyed yet still look practically brand new right down to the outsole. In other words, Rothy’s makes good shoes. If worn regularly, these loafers will practically pay for themselves.

Sesa is a niche Italian brand offering exceptionally well-made, small-batch, hand-crafted leather shoes. Its most traditional-looking loafer is theNew York Loafer Sister(there’s also amen’s Brother version), which looks and feels like a very subtly zhuzhed-up Weejun — the leather outsole is slightly thicker, the welt extends just a bit farther, and the toe is just a tad squarer. It’s a beautiful and very high-quality shoe, and the price feels fair for what you’re getting. But I’d still recommend starting with the Weejuns (and saving $100 in the process).

Full disclosure: I designed this pair, so this is an exceptionally biased take, and also why it didn’t feel fair to put them on my must-buy list. Still, these are one of the few pairs of shoes I’ve designed and actually want to wear: They have a gathered-toe detail that’strendingrightnowbut is still mellow enough to stand the test of time, and the minimalist leather strap that weaves through the vamp adds uniquely subtle interest. The almost imperceptibly square toe is on the narrow side and the heel is a bit higher than “normal,” a combination that gives these loafers a more refined and feminine appearance than anything else on my list. I’d like to think they’re what present-dayCarolyn Bessette-Kennedymight put on.

What I’mnotbiased about is the quality: The upper is made of a luxurious lamb nappa that feels predictably soft but substantial, and the stitched outsole has a thoughtfully rounded edge and an artisanal curve that feels handmade in the best way. The outsole and heel also have rubber plugs, a sign of quality that helps to extend the life of the shoe. No expense was spared — which explains the extreme price tag. Still, it’s a cost you can feel when you wear them and a worthwhile investment.

[Editor’s note: TheLeather Dylanis currently sold out, but you can sign up for a restock notice. And if you can’t wait, there’s alsoa nubuck version.]

These were a really tough call. Not only do I love the way they look, but they’re also one of the easiest loafers to wear — which, in this case, isn’t necessarily a good thing. They have a pliable, almost floppy suede upper and an unlined collapsible heel that feel broken in right out of the box, but are also easy to stretch out — I have them in both a 10 (my regular size) and a 9.5, and it took less than a month’s wear for the smaller size to fit just as well as the larger. The incredibly flexible rubber outsole is more durable and much easier to replace that the nibs on a classic driving moc, but it’s also very thin and merely glued on, so I’ll probably need that replacement sooner rather than later. And while all of these characteristics are common in cost-effective shoe production, they also make the nearly $200 cost hard to justify: It’s a fair price for shoes you’ll want to wear all the time but also a bit too high for ones that won’t last as long as some comparably priced pairs.

There’s nothing wrong per se with this innocuously classic pair: They have a flattering almond toe, a “whale tail” penny-keeper strap with beef-roll edges, and what I think is the perfect low heel height. As far as mass-market production techniques go (i.e., a glued-on rubber outsole), they’re also very well made — J.Crew may fall under the fast-fashion umbrella, but it tends to deliver on quality. The Winona is even one of the brand’s top sellers. Still, why buy a Weejun look-alike with poorer production value when you can getthe real thingfor $50 less?

A fashion-designer friend with exceptional taste was recently raving to me about her Massimo Dutti loafers. She noted the styling, of course, but was especially pleased with their quality-to-cost ratio. While I’m somewhat wary of the latter given their production model (the brand is under the umbrella of fast-fashion pioneer parent companyInditex), I really like the look of them, and they’re well priced enough to at least merit a try-on.The Soft Penny Loaferis yet anotherCBK-inspired pair, and I’m also eager to test theGathered Split Leather Loafer, which feels reminiscent of The Row.

I’m not usually a horse-bit-loafer girl, but given the true excellence of the brand’sBit Loafer, I don’t need persuading (just more money).

I recognize the appeal of a lug loafer but have yet to find a pair that’s right for me. The Elba feels like a promising way in: While not a true lug sole, it has an oversize, slightly splayed heel and thick, jagged welt that imply a lug’s chunkiness but in a more grown-up way. This pair is also very well made, and you can addhardware.