For the longest time I held on to a pair of high-waisted black dress slacks, circa 1987; they buttoned up the side. They were pre-pregnancy pants from my early career wardrobe. I was hoping to one day get back into them, but all the exercise and dieting in the world just would not make that possible after having two babies. Well, at one point I *did* get into them (just barely), but of course they were awfully dated. Still I held on to them. But, I finally let those pants go a few years ago.
Otherwise I confess I still have several items from around circa 1998 (when I re-entered the workforce after taking 5 years off to raise babies). Though I have been slowly releasing those. I kept them "just in case" but also because there was a window of time when my own daughters could fit into them. So, for example, the classic navy blue interview suit got worn by DD2 in high school when she needed to dress up for a debate. One of my cocktail dresses from that era -- which became too short/too tight/too hoochie for me -- has been worn by DD1 once or twice before finally being released. I'm pretty sure I have a classic black cocktail dress or two still in the farthest reaches of my closet that are around that old. But formal dresses have more longevity.
Let's see.. I also have a circa-1997 brown silk button down that I'm having a difficult time letting go. It went with a houndstooth pencil skirt; I used to wear it with dark brown tights and chunky brown booties. It was one of my favorite outfits. The skirt is long gone -- although DD2 got to wear it for a year before she grew out of it. I pulled that blouse out this fall and I've been trying to find a way to wear it, to no avail. I know it has to go, but I have some serious emotional attachments to it.
There are many other pieces that I let go... but still remember fondly and vividly. I get sentimental about my clothes. In fact, I can tell you exactly what I was wearing when I met my first love in high school (Levi jeans, cowboy boots, red velour long sleeve top). And I can tell you what I was wearing when I went on my first date with DH (I only just released the black BR merino wool V-neck circa-2002 sweater; the gray Gap bootcuts were released long ago).