i bought this boot because i thought it would wear well to work on uglier nyc days. the boot does this with aplumb. nice fit (though i'm still breaking them in. I have to tie them loose on top because the top left of the boot kinda rubs me). This is a very versatile boot that looks great with dark jeans or dress khakis. and Timberland has a great repair policy. I have two other pairs of timberland earthkeepers (an oxford and the workboot) and like how light  and comfortable they are. highly recommended.