50 Pairs Of Vintage Loafers You Can Buy Right Now

Slip into some pre-loved loafs that are worthy of new life in your rotation.

Welcome to Shoesday, a weekly column, sent every Tuesday, about shoes.

I recently did a round-up of my favorite loafers on the market, which, if you’re interested, you can check out here. But for those sticking around, today I’m circling back to the subject of these stylish, timeless slip-ons, but through a slightly different lens. Instead of scouring the market for new options, this entire 50 item (!!!) list is dedicated exclusively to pre-owned loafer gems.

The main reason for doing this? For me, few things hit quite like stumbling upon the perfect vintage pair of shoes—or any clothing item for that matter. It’s like discovering wearable treasure that, given the unique nature of each find, you know only you will have.

But also, I get that not everyone is a sicko like me who wants to spend their nights endlessly scrolling and adding shoes to their eBay watchlist. So, I did the hunting for you. Below, you’ll find 50 pairs of lightly-to-well-worn loafers that are big on character, already broken in (your heels will thank you), and in most cases, available for wayyyy less than their box-fresh counterparts.

I tried to make the list as wide-ranging as possible—different styles, brands (everything from Polo to Gucci to Florsheim to GH Bass to Bally and more), and sizes—so there’s something for everyone. Also, I know I said “vintage” in the headline, and indeed that holds true for the vast majority of what you’ll find below. But a small handful of these pairs, technically speaking, lean more toward the “secondhand but not quite vintage (yet!)” category. Just know I included them anyway because they were simply too good to pass over for one reason or another, from offering insanely good value, to being flat out great-looking shoes.

Anyway, take a look, see what speaks to you, and as always, enjoy!!

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And now for today’s post…