Along with cowboy boots and clogs, loafers are arguably the most relevant shoe in streetwear right now. Ironic, considering that they’re also the textbook definition of a “classic” — but in fact, the best loafers for women embrace that dichotomy. In the edit ahead, you’ll find the penny, tassel, and horsebit loafers seen on virtually every well-coiffed person over the past 100 or so years, as well as the uber-modern versions, like the ones with chunky lug-sole platforms, that you’ve just started to see on fashion people all over Instagram.
Depending on how you style your loafers, you, too, can play around with aesthetic tension. Channel a cool, quirky grandpa with a pair of pleated trousers and a sweater vest, or preppy Princess Diana in clamdiggers and a cardigan. Loafers worn with crisp denim and a top-handle bag epitomizes uptown polish, though any chunky iteration naturally skews downtown-cool. And when in doubt, wear them with socks. The more conspicuous — like, ribbed-gym-socks conspicuous — the better, as far as tastemakers are concerned.
The good news is that there’s pretty much no wrong way to wear loafers, whether you’re being particularly intentional with your outfit or not. Once you break them in, you’ll reach for them over your slippers when you need to run out for errands. (Yes, you can wear loafers with pajamas.)
More good news: Some of the best loafers for women are available on Amazon Fashion, so you can have your chosen pair in hand (and on foot) in a matter of days — but you’ll be wearing them for decades to come.