non-garbage /effay/ Boots?

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Hi /out/,

I need a decent pair of boots for walking in the woods, highlands, and beach in any weather that I can also wear when I'm not /out/.

Right now I wear some brandless old pair of 6" leather boots, and I've had them so long that I can't remember when or where I got them. I wear them everywhere unless I'm going to a wedding. I've got a lot of use out of those bastards, and never taken care of them. They're totally ruined, they make so much noise when I step and they have more scars than I can count. I love them, but the soles are so full of holes now that my feet get wet even when there's barely been rain.

I wear boots no matter what. Most walking boots aren't the sort of thing you can wear when you're not hiking, and most "work boot" brands that are waterproof, were built to last, and look respectable have become fashionable and now solely produce overpriced chinese garbage that would look like shit after a single trip to the forest.

Is there anything out there that looks good and stays looking rugged but nice over time? Timberland is a fashion boot, I assume they're barely even waterproof. Iron Rangers don't look like they were ever fucking work boots to begin with; same goes for 1000 Miles.

I just want something that's comfortable to walk in and will take a beating, but I could still wear around the city day-to-day. What's my best option? I'll spend up to $500 for the right thing.