I have never considered wearing two watches at the same time. As you have learned, I feel awkward when I am not wearing a watch at all, but I think I would feel even more awkward if I was wearing two. There are some people, however, who really enjoy rocking two watches at the same time.
Twice in the last month I have run into someone who was wearing a watch on each wrist. I had the opportunity to ask one of them about it, and he told me he wanted to make sure his Colt GMT and Rolex Milgauss both got enough wrist time.
Nicolas Hayek, former CEO and Chairman of the Board of the Swatch Group, was a major figure in the watch industry who was known to sometimes wear two or more watches simultaneously. Meanwhile, soccer legend Diego Maradona typically wears two watches at a time while traveling. He was wearing two watches throughout the 2010 World Cup in South Africa. He sets one watch to the local time and the other to the time in his home country of Argentina. I assume he does not own a GMT watch…
Seeing two people wearing two watches simultaneously made me think about whether it could ever become a new fad. Do you think this could catch on?
The Hourology Report 
I don’t wearing two watches becoming a new trend. At a jewelry store where my wife and I go to check out pieces, and have repairs done, there is a lady who looks as if she wears every ring she owns. It just doesn’t look “right”. I put wearing two watches in the same category. When traveling, I’ve been known to wear two watches until I got to my destination. I felt more secure wearing them than carrying them in luggage.
To me, wearing 2 watches is like wearing suspenders and a belt. Why?
Nah ! I don’t think so. It looks kind of weird. If you really need to have two timezones you can wear a GMTor any other dual-time watch . If winding is the issue……………….. there are things called watch winders.
I remember visiting an AD in St. Thomas and the guy working there was showing me his Superocean. He then proceeded to show me his Omega on his other wrist. I thought to myself, I really hope you only do this at work. I truly don’t see the point in wearing 2 watches when there are several models with 2 time zone functions.
I would have no problem rocking 2 watches. Obviously I would not be doing it for function as I would simply buy a GMT if I needed two timezones. If you have the confidence to pull the look off then the 2nd watch acts more like an accessory than a timepiece. Hublot Big Bang Ceramic on one wrist and a Rolex Platinum dial Yachtmaster on the other.
I sure hope it never catches on. It looks ridiculous.