Because I'm a good friend, and I know we have good friends who are of the male persuasion who frequent our humble blog, I did some "shopping" and found these shoes that I think are very cool.
The Frye Marco Crepe. The Frye Company is, according to their website, "the oldest continuously operated shoe company" in the U.S. In the last few years, their popularity has made a comeback with their Engineer Boot and Harness Boot (which I own in black and LOVE) for women when everyone from Rachel Bilson to Keira Knightly to Jessica Alba was seen clomping around in them. (Although native New Yorkers will tell you that the resurgence of these boots started somewhere downtown...)
Rich in color, great worn-in look, and has the right balance of urban cool nonchalance vs. old-school practicality, these ankle boots would look good with jeans, khakis, and possibly casual dress pants.
$210, at Urban Outfitters.
How'd I do on recommending a guy's shoe? Did I pass? Oh, who am I kidding - that's just silly! Of course I passed; I have great taste and these shoes are so awesome that I'd wear them if they made them in smaller sizes.