If you must have a female role model, may I recommend Katherine Hepburn or Angelina Jolie: lots of pants, lots of attitude, no jewelry. Please, not Madonna. And certainly not Lady Gaga. No one wants to come home to that.
DRESS PLAIN. You don’t have to dress to look particularly masculine. But if you’re not sure what looks good on you, don’t wear a lot of stuff. You can never go wrong with a tee-shirt, blue jeans and a very expensive blazer.
GOOD SHOES. You’ve heard this forever but it’s true. You can run around in a tee-shirt and jeans, a cheap white shirt and black pants, what have you, but one glance at your shoes tells any knowledgeable person whether you have taste or not. They should be leather, brown and plain. And please do not wear sneakers all the time. You’re a big boy now.
NO FUR COATS. In the fashion business, the adage is, “Furs add ten years to anyone’s age.” That great fashion goddess Babe Paley never wore fur. This is not about animals. This is about you.
TIGHT CLOTHES DO NOT MAKE FOR TIGHT RELATIONSHIPS. Isn’t the short shorts and tank top a little bit like the big-breasted girl in the pink angora sweater? A little desperate. Being cool doesn’t mean wearing skimpy clothes.
DO NOT WEAR INAPPROPRIATE SHORTS. That is, above your knees. Get rid of the shorts of your youth.