Don't ask, Can I imagine wearing this? Instead ask, Can I imagine this ever being the best possible thing in my closet to wear?
Works for other things too.
Evan Williams is an American entrepreneur who has co-founded several Internet companies, including Pyra Labs (creators of Blogger) and Twitter. He was born and raised on a farm in central Nebraska. He lives in San Francisco with his wife and two sons. He likes long walks in the city, tofu, and bourbon. He has published this blog for over a decade and keeps meaning to write more. You can follow him on Twitter.