Yes, actually, twice. The first time was when I was a newbie and I saved up for a shirt, pants, belt, shoes, socks, headband, and glasses. I was really happy. I'm actually decently proud of that one, cuz all things considered, it was a very nice and generic outfit for a normal person.
The second time was when I finished my crazy king avvie that involved my proudest item combo moment, putting together a skirt, belt, underwear, socks, leggings, and probably something else in order to make the illusion of the pants that were perfect for the avvie. It's the best matching and organized clutter-style avvie I can bear to make. *dons it now* In particular, I did it back in 2009 or so, so none of the newer items. (Never got a chance to update it, too many new things)
I keep it as an outfit now just because it's become stereotypical me. I occasionally do derivations from it, or something more simplistic when my eyes start to bleed. xD