Okay punk, you're getting a little newbie hazing here, but I'll start the ball rolling with some simple tips. First, wear white, straight collar, broadcloth shirts. No button downs, no oxfords. You could spend from $2 at a thrift store to $500 at a boutique. But it's a simple solution so you lose the t-shirts and the flannels or whatever else you kids put on these days. You might also consider getting a white shirt as described above in french cuff. The shirt should be narrowly cut for you, by the way. Big and blousy is not the look you want. Second, graduate from jeans or other cotton pants to wool trousers, either with flat fronts or small pleats. The pants should be narrowly cut and possibly even have a little pegging towards the bottom. To step it up a notch, get them on the short side so that the cuff just brushes the tops of your shoes without breaking (i.e., hanging straight down with no bagging). Again, you could go thrifting or spend oodles -- depends on how much time you have (if your college time is like mine was, you can spare it) and how authetically Sinatra you want to look. You might try a relatively cheap place like Benetton during sale season as their stuff might fit the bill while being up to date. Third, wear long, thin black shoes. Loafers or lace-ups. Consider white dress socks underneath to accentuate the short, pegged trousers. Fourth, either start wearing a jacket or a cardigan. Back in the 50s, cardigans weren't old-man wear. After all, how do you think they got to be old-man wear? Men who wore them when they were young and stylish got old. Jacket should have thin lapels, little padding, narrow cut. Fifth, start smoking and drinking apple juice (old legend that he used to drink apple juice and tell people it was whisky while forcing them to try and keep up). Wear your hair short. Use a toothpick. Now as to the why? Only you can answer that. We all have to find our own style icons and run with it. By the way tips were for the general '60s swinger look, rather than his 40s tweedy, big-tie look.