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The Red Wings and chukkas are good suggestions. Boots are one of those things that are worth investing in as they should last you a very long time. Part of buying a pair of leather boots is waterproofing them with mink oil and other synthetic options.

I just got these Thousand Mile Boots from Wolverine in the Rust color a month ago and they've been awesome this fall. Perfect on the motorcycle, in the rain in the Northwest, hunting, they can dress up a bit but are right at home in the most casual environments too.