I was recently at a sheva brachos that was also attended by JewishCube. We got to talking about personal and spousal preferences to Orthodox Jewish males wearing wedding rings. I know that in the more yeshivish crowd, wedding rings are practically unheard of, whereas in the more modern orthodox crowd, it is pretty common. I don’t really consider myself to be in either of these categories, but I do not wear a wedding ring. Nor does anyone in my immediate family. I was curious as to the background of the wedding ring and how the practice came about. With women, it obviously goes back several thousand years. This is how Jews married from the beginning.
The Wikipedia article on wedding rings gives some interesting background. According to the article, the double-ring ceremony was started in the late 19th century by jewelers as a marketing tool. If everyone would do a double-ring ceremony, the jewelers would get more business. But it never became widespread until after the Great Depression. By 1940, double-ring ceremonies made up “80% of all weddings as opposed to 15% before the Depression.”
So this really is a recent phenomenon amongst non-Jews, and even more so, amongst Jews.
After doing a quick search on the subject, I came across this thread on a discussion board. It says there that according to R’ Moshe in Even Ha’Ezer 3:18 and Even Ha’Ezer 4:32, giving a ring under the chuppah or shortly thereafter should not be done. However, “even though perhaps it is repugnant for a God fearing person, one apparently should not forbid it in my humble opinion.”
What it boils down to, in my opinion, is personal preference.