I wear a pocketwatch all the time. I usually carry a Hamilton 950 which is from about 1910. I carry it on a leather pouch on my belt and though I use a chain you do have to be careful because chains can snag on just about everything. The leather strap with a fob on the other end was how working stiffs carried them years ago and it's much safer that way. If you search Eboy you can get a nice sterling silver vintage chain for a pretty reasonable price which is better than the plated garbage most places seem to have.