combine fashion and comfort. there are fashionable items that are really comfortable to wear, you dont need to buy stuff that looks like you just got out of the red carpet, for example, during Friday most offices allow their staff to wear casual clothes, a good pair of black jeans, or lets say your good old 501's can be worn with white Tshirt underneath a good fitting/nicely tailored blazer, and black pumps, this look will make you look reliable and professional during the working hours and at night you can just remove the blazer and hola! you're ready to party.
I'm also not keen on following fashion trends, so I find myself buying clothes for comfort and practicality rather than fashion. I didn't even follow the skinny jeans and leggings trend when it was popular since I'm not comfortable wearing tight clothing.
I think I buy based on comfort as well. I like clothes that fit well and flatter my figure. Tight fitting clothes are too restrictive to wear to work so I like to be comfortable. I still like to wear clothes that are fashionable too. I find that since most of my wardrobe is based on comfort that I'm able to wear my clothes year after year and not feel out of style. Clothes that are so fashionable they are out of style in a year are not what I buy. I need to make them last a few years so I stick with a classic look.