Any leather boot is only as good as it is prepped whether done at a factory or by you. The guy that went camping just took em out of the box and jammed on em. Seal the sole stitching with seam sealer, oil em like you should, and mist em with a leather spray and they are great for hiking in rain. Not a rubber rain boot though so deep puddles or standing water aren't their thing.

Are these good for Chicago winter?

Oil em up. Mine resisted daily salt exposure just fine and are great in even deep snow. I wear mine year round and we get a day or 2 around zero, average winter day is 13-20 for the high. Two layers of Costco merino socks and I'm loving life. In the summer its constantly high 80s to 100, sun every day and with cotton socks they stay comfy. Great boot, crazy good price. Not a rain boot lol

Can you use shoe polish on them when they're scuffed up?

Use mink oil remove scuff marks and protects the boots make them waterproof

are the boots slip resistent

Yes including oil slips, as per what’s written on the bottom of the boot.

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