Can't believe nobody mentioned combat boots! They're durable, look suitably badass, and actually fairly comfortable when broken in. And available at any surplus store or military/law enforcement supplier (Brigade Quartermaster, US Cavalry, and Ranger Joes all being good ones). For the issue styles, the green jungles (canvas side) are the most comfortable, but aren't as good with the ankle support; Jump boots are nice and sturdy but not the nicest to walk in; Tanker boots (with the straps) are good all around.
I usually wear Magnums, a cop-style combat boot, synthetic leather with nylon side panels; comfortable, light but tough, good support. I have to say my actual issue boots are better in hot weather cause the real leather breathes better. When it's really cold out I wear my Matterhorn winter combat boots, keeps the toes nice and toasty.
Of course, I already owned a ton of boots that I don't have any other use for now that the Army's gone to the stupid suede ones. How can you have a decent private that has never had to spit-shine????