When I look at my wardrobe, there are few things left that I've had nearly my whole adult life. First of all, I'm slightly larger than I used to be (as I should be), and secondly, I tend to buy not-so-expensive clothes that either wear out or go out of style. There are a few shirts, and a few dresses, however, that have managed to stick with me over the years. I'm reminded of an American Eagle plaid jumper, purchased in 1997 (when beginning 9th grade), that I still wear; a madras blouse purchased from the Gap in 1998, and this black and white sweater dress, bought for $15 at Bergner's department store circa 1999. To prove I'm not too old, I even remember the details of the transaction: my mom found the dress on the sales rack, and instantly knew (with he excellent fashion sense), that it was right up my alley. I've been loving it ever since, and even wore it to work recently:
Dress: "French Twist" via Bergner's, shoes: Etsy
Maybe it's a little 90's, but to me it seems pretty timeless.