I think I’ve probably had some version of these since college: they’re incredibly versatile and have seen me through many style identities. They can skew punk, preppy, Euro-classic or pretty much anything else, and they’re (usually) highly walkable. I love the neutral light brown hue of these and the cream-colored sole. They also come in black.
These are from Ferragamo and still aren’t cheap even marked down, but I’m very tempted by them (because of the platform sole, of course).
Here’s a pair that rings in under $100, and is satisfyingly clunky.
Whereas these, from Vince are a cool combination of clunky and polished.
OK, these are actually sneakers, but I think they’ve got a very chill skateboarder-y vibe.
This splurgy pair looks slightly treacherous, But I’m still a fan.
I like the streamlined look of these rain boots.
I dig the dandyish details here.
I don’t much like brown shoes, but I included this Madewell pair because I know that some of you do. They also come in black, BTW.
I live in my Blundstones and love to travel with them because you can literally walk forever in them. This pair has a hint of a heel—mine don’t—but I’ll bet they’re every bit as walkable.
This waterproof pair has a bit of a tough-girl edge, but just a bit.