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This is one that I struggle with. I seem to be stuck somewhere, not in a particular time warp, but with a particular non-look look. I had one of those professional makeover sessions and it was helpful. The person was able to zero in on good colors for me and a particular style. The only problem is the style is "athletic" and since letter sweaters are not in fashion and going to work in sweats is not an option I'm still fumbing, but as Kristen says, Tim Gunn offers some good, solid advice.
If you're asking, you probably know the answer! Check out my recent interview with Tim Gunn—he mentions how important it is to dress age appropriately.
For me, a big clue is who else is in the store while I'm shopping. If the average shopper age in the store is high school senior and you haven't walked the halls in ten years, it may be time to look elsewhere for your fashion needs!