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Depends what you're buying. Here's the secret;

Norwegian Army M77 boots.

$130 brand new army surplus. Incredibly high quality, genuine leather, indestructible build, totally waterproof (I have literally submerged my foot past the ankle in puddles and not so much as gotten my sock damp) and extremely comfortable.

Secret number two is how you wear them. For proper boots like this you need to a) buy a separate inner sole, and b) go up a half size to allow room for thick boot socks.

With those two things in mind you will have a boot that can tackle anything you throw at it. They're real leather (and I mean thick, full chap leather) so you will have to break them in. Rub them down constantly with mink oil to keep them moisturized so that they'll become more flexible. They'll be uncomfortable at first, but give it time. And once they're broken in, they'll basically last the rest of your life if you treat them right.

Am I gonna wear them all the time? Fuck no. Give me a good pair of Vans anyday. But if you want nice boots that last, this is how you get them.