I don't think I've ever had anything reversible, now that I think of it. Hmm. Oh, I think I had a tote bag that I only used on one side because the other wasn't a color that worked well for me. I tend to use things one way -- a jacket with zip-out sleeves seems to stay a jacket and never get used as a vest; those zip-leg pants seem to get worn as pants, but that's a gear thing.
I do have that Veronica Beard blazer with a black hoodie dickey that I purchased separately, but we are only just now getting to blazer weather here, so I haven't worn it with or without the dickey yet. Soon! I have a feeling I'll wear the dickey more than not, since it casualizes the blazer.
I think the only thing I really take advantage of, as far as wearing it in multiple ways, is a pareo I have that works as a beach cover-up tied a couple of different ways, or a skirt, or a shawl.