I think you reach a point in life where the obsessions of your youth are no longer quite so important as they once were. While flipping through an issue of Details this morning and seeing the article that screamed "Must Have Looks for Fall" I got to thinking how silly it all is. Fashion, like a lot of things in life, is transitory. What's hot today is going to be considered dated tomorrow, so why worry about it? That's why I think it's important that people find their own sense of style. Find clothes that are comfortable, match your lifestyle, and don't break the bank—because sooner or later all of it ends up at Goodwill or in the garbage.
For me, my personal style has been T-Shirts, Polos, and jeans for as long as I can remember. Once upon a time they were the official uniform of the clone brigade in the bars and I always felt less than properly dressed when I showed up in a polo shirt that sported an English flag instead of a green alligator. (Even back in the day the premium paid for that little alligator was more than I could afford. Funny how things never seem to change.)
Out of habit, I still wear most shirts tucked in. After seeing some makeover show several years ago I know that alone has me teetering dangerously close to "doddering old fool" status, but I'm comfortable with it. When my shirts aren't tucked in, they look (to me) like they're hanging down to my knees and it just doesn't work on this body. Maybe it would look better if I didn't have the massive belly in the way. (BTW, weight is something else I no longer obsess about. I found it's easier to just love and accept myself as I am instead of obsessing over every plus-or-minus 5 pound swing I go through. It's sad when I read through old journals and remember that I was convinced if I could only lose 20 pounds―while easily fitting into size 33 jeans―all would be right in the world. To my younger self I say, "Get over it. You're perfect just the way you are."
I never used to wear belts with my jeans. Of course, back then I had a butt that kept my pants from sliding off.
There are some things that I wore when I was younger that I won't wear today: white jeans. Leather jackets. Anything with a "Members Only" label. Frye boots (another one-time seeming requirement for going out dancing).
What about you? Have you found a style that works for you, day in and day out?