It may sound funny, but the best boot I have found for exploring with, is the duck boot. You do need one which comes up onto your ankle rather than the one which is like a shoe. If you wear the wrong boot you may as well go exploring in open toed shoes. (I will admit to doing almost that a few times, but that doesn't mean it was a good idea).

Qualities important in a boot for urban explorers:

• Weather proof (water resistant or water proof and include snow in that list because snow is just colder water).
• Thick bottoms (you don't know what you might step on, into or worse).
• Fitted to your ankle (so they don't slip off if you walk through mucky areas).
• Easy to slip on (because you don't really want to be struggling with footwear when you could be out there... looking around).
• Packable and durable, more or less (boots you can toss around in the back of your car or stuff into your backpack are a plus).

As an extra tip, stick those insoles into your boots. You get extra cushion for your foot and it helps if your feet get wet from outside water or sweat from your own feet.

My duck boots are a size too big so I can wear extra socks if I was out with them in winter. Or, I can easily wiggle my feet into them and out of them again. This does make them a bit awkward to walk around in so size is a relative issue.

The perfect duck boot for me would have nothing to tie up and just be slip on. I was surprised to find some really great looking boots for explorers on Amazon. I wonder if anyone thinks of them for more than hiking or hunting or whatever other people do while wearing duck boots.

Real urban explorers wear duck boots.

Just kidding about that. I think they are great, but I explore in rural areas. People who explore in sewers, drains and tunnels probably want to wear boots up to their chin, or so. People who climb rooftops to photograph above the city, might want a lighter boot with more traction. So, your boot choice will depend on where you are going. Plan ahead!

Don't try searching for "explorer boots" (you just get Dora).