I might turn my closet quickly but one thing I never get rid of is a great pair of boots. Some of my boots I’ve owned for 10 years, others I just bought last month. Regardless of your personal style cheap boots are never good boots; you want them to wear in and become old friends, not a trendy throwaway piece of crap that will give you blisters.
These Merrell boots, available from REI are as functional as they are cool. Merrell manufactures hiking shoes so you know these will feel like heaven on your feet and be sturdy.
When it is cold and rainy outside the last thing you want is clammy feet. These Cole Haan rainboots from Zappos have Nike Air technology so you could wear them all day and remain dry and comfortable.
If you are looking for riding boots these Michael by Michael Kors, available from Dillards, perfectly fit the bill.
If your holy grail of boots is the ultimate shit kickers it doesn’t get much better than these Frye boots I found on Ebay. Since I don’t wear brown or a size 9 these babies are still up for grabs.