I don't see watches really looking dated unless they really scream a trend. I think they are more a personal style choice than anything. I particularly like double-wrap watches these days, and I have two -- the black one here in my Finds and a lovely navy blue band Hermes that was a gift from my husband.
I really enjoy my two rose-gold watches, one with a fairly subtle mixed-metal effect floral detail, and the other a stone-look face and grey band.
I also have a smaller profile, dressy mixed-metal Skagen that I will sometimes wear for dressy events.
And then there is an ancient black leather strap and mother of pearl face watch I bought in Switzerland when I was about 26. I still love it and wear it when I wear gold since it has some gold in it. To my eye it is timeless.
But my old standbys are my Philip Stein watches, especially the dual-face one as it's my travel watch. Unfortunately, both need new batteries right now, and the dual one needs to have the crystal replaced. The store where these were purchased no longer carries Philip Stein, so having them serviced there will take a long time. I'm looking into other options to have these watches fixed. I have several leather bands in a variety of colors/textures -- white, silver, black croc, teal -- so I can change out bands easily on these watches for a variety of looks.