What amazed me when I first saw red stripes with a navy and yellow polka dot tie (M Magazine- 6/87) was clarity. Looking closer, I see primary colors from 7th grade art class. I can do more: Reverse the tie and shirt color. Use navy /yellow rep instead of polk dots. Red gingham shirt instead of stripes. The choices are endless.
That's looking closer. Using your own creativity in the most basic of functions -- getting dressed. And it should only matter to you because only you will know. That's really what life is. And then it won't matter how much money you make or what parties you go to. Something far better is going on since you're making the rules.
It's funny. People I know who work hard at being fashionable usually hail from very un-hip pasts while people who distance themselves from hip are some the hippest people I know. I wonder why that is?