Kenneth Cole Foot Note Boot – $59.99 
Do women really notice a guy’s shoes right away? They say that a man’s shoes are one of the first things a woman will notice when he walks into a room. Even if that’s not the case, it’s still a good idea to have a solid pair of brown dress-boots on the floor of your closet.
Or, on your feet as the case may be.
Look for something that could be described as “sleek.” Keep away from boots that the toe is super-boxy, over-detailed, and make sure to opt for something without that pesky elastic gore siding. One zipper should get you comfortably in and out of the boots, and these have two so you should be fine.
The brown color (sorry, Mahogany) is what’s on sale. Wear them with dark jeans and a cotton unstructured blazer.