Oh! yes. 
I seem to have one thing at a time that I can't live without, rather like a series of best friends iyswim.
When I was a teenager (about 17+) it was a black, thick cotton Laura Ashley skirt which was long, and gathered, and full, with a proper waistband, which was passed on to me by my sister.
I lived in it - the woman on the cover of Surfer Rosa wore one like it. It made me feel like me. It eventually literally fell to pieces, was faded, torn, etc. I even wore it behind the bar when I worked in a pub over Christmas so it smelled of beer and cigarettes and got soaked 
Poor skirt. I'd be more respectful now.
Then I had a silk, fitted dress that had been my Grandmother's - 1940s - again it fell apart, it was like a dark greeny and yellowy fine check, with slim half sleeves with a little frill at the cuff, and a v neck front and back, and very tailored with a sort of handkerchiefy panelled skirt part. It did up with hooks and eyes.
I wore it to pieces, together with charity shop cardigans with holes in and attempts at dark eye make up.
Another was a plain cotton shirt from an Indian shop which was just lovely.
My most recent is I suppose a slim fitting dark moss green wool coat from Toast which had dodgy silvery lining that tore to bits, but I still wear it despite having bought a replica in the archive sale.
Don't know why I loved these things so much. Most of the time I find dressing hard work! Often I wear the same stuff for a few days or weeks as I'm not great at decisions.