I don't. It's not that I haven't tried, it's just that I don't get it. I remember as a teenager, being really perplexed by not being able to put together an outfit like everyone else did. There were always discrepencies between what was in the fashion magazines and what people really wore. For a while I stuck with jeans and sweaters because it was ultimately safe. How I found what I really liked was by watching movies and television. I fell in love with the fashions worn in Chariot's of Fire, the Giorgio Armani clothing that adorned the fashion models shown on Style with Elsa Klensch, many of the outfits worn by Lisa Bonet on The Cosby Show, and later the fashions on the BBC series, House of Eliott.
This led to a certain freedom in how I dress. As my eldest daughter, Emma, tells me, "Mom, you have a style, it's just not in style!". Well, that suits me just fine. What got me thinking about all of this, is this graphic that Hipster Christianity sent out on Facebook. My suggestion would be to skip the cycle and wear what you find to be beautiful and useful. If you happen to land on the cycle every once in a while, no worries. Life is too short to be concerned with being too hip or not hip enough.