Men should dress for their work but none of this stupid hipster or trendy shit we see today. Working in IT I was expected to have khakis and a button down which was fucking stupid. When you have to crawl around under desks or fish cables under a raised floor in the datacenter it is god damn pointless. Let me just have my jeans and a comfortable shirt. When I worked outside in labor I was in Jeans, boot's and a weather appropriate shirt/jacket/gloves/etc. Outside of work might be more what you are thinking for the question though. In that case, I still go with the "working man" kind of attire but clean and well cut. Find a tailor, buy some quality shirts that fit you fairly well and then get them tailored, same thing with pants. It used to be that you would do this (everyone would) and you didn't have the "one size fits all" kind of stuff in the stores. You look better, the clothing fits better and your are more comfortable. It is a investment but you only need a few sets and they should last a long time as long as you bought quality and rotate them regularly. All men should have a few outfits for more formal situations but the rest should be clean, well cut and casual unless it is for work. Then it should be practical for the job you do.