If last winter's pragmatic shoe of choice was the ubiquitous L.L. Bean duck boot, please excuse us if we're already pondering what the steadfastly approaching winter months will have in store for our feet. While the L.L. Bean classic was cute and all -- and functional to boot (get it?) -- we're feeling like we may need to shake things up a bit this upcoming season, and we've found the perfect thing: Red Wing's Wabasha chukka boot. It's surely masculine and sturdy -- perfectly in line with the trendy 'heritage brand' sensation that has ingrained itself so thoroughly in menswear these past few seasons. It's decidedly handsome, from its burly leather laces to its moccasin-like body. The leather has a pre-worn look which is a nice touch (who likes buying a pair of shoes and having them look so damn new? Not us.) We're also loving the understated inlay of forest green waxed canvas on the upper ankle, a nice touch to set it apart from Red Wing's more omnipresent Classic Lifestyle style (don't get us wrong -- it's a great boot in its own right -- it's just become a bit of an expected winter staple at this point.) And because it's from Red Wing, you can expect a little love in all the details, like a leather insole and reinforced hand-stitching, done right here in America, not shipped off to a factory overseas. Not convinced yet? Well, the shoe comes in just under $250, which, while not exactly dirt cheap, is completely reasonable considering that it melds style and substance so effortlessly.