I still have the same gucci brown sukey as i use as my avatar. haha. I haven't used it in years because it doesn't stay on my shoulder. I decided this winter to try a Crossbody strap. When I attached the strap he looked good. Will wait fro the winter to carry.
Last year I acquired a vintage large horsebit hobo in chocolate guccissima leather. Every single time I carry it I get compliments. Even people who don't know are drawn in by the quality of the leather and craftsmanship. Many are shocked when I tell them it's a nearly 20 year old bag. Quality is timeless. So, if it fits your own personal style, I say go for it!