People Wear the wrong things, How do you tell them?

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Hi guys, can you tell me why people insist on wearing clothes and shoes that are way out of date, I dont mean by a couple of months or a couple of years. I mean decades. A good friend of mine loves to wear beatle crusher shoes, They are these big black things with black and white checks on the front. I dont have the heart to tell him that they look terrible on him, but sometimes needs must. Have you ever came across this and how have you handled it? The worst thing i find is that he really thinks he looks cool.