How to choose clothing?

Presumably you’re smart enough to not wear the same thing to the office that you’d wear to the beach, but if you look through your closet, you’ll see a lot of consistency: your comfort clothes (you may need to jump-start this part of your wardrobe a bit) and stuff that is more costume that you wear to make a statement. It doesn’t matter what the statement is as long as you’re aware of the statement and it squares with how and what and why you want to present yourself.

You can start with your closet if you like, and get rid of all the stuff that doesn’t make you look and feel terrific. All of us have more clothing than we need, so if something doesn’t look and feel wonderful, give it to a friend or Goodwill, but get it out of your closet. If your shoes hurt your feet, get rid of ’em. Nothing makes a person look worse than when their feet hurt. That’s the easy part.