la mer's brown leather simple wrap watch ($76) has been on my wishlist for a while now. i love the classic face and the unexpected double strap. la mer also carries the simple wrap in really fun colors (i love the neon pink and the orange!) as well as a line with chains and charms. reasonable prices and customization options definitely put this line at the top of my list.
i gave my boyfriend j.crew's timex military watch ($150) for christmas and he loves it! the face has a beautiful vintage feel and you can swap out the black strap for bright solids or preppy stripes (current promotion is $30 for two straps, so why not both?!) on a whim. perfect as a gift or a way to add some androgynous appeal to your own look. (i will attest that the strap can be tightened to the size of my wrist!)
i love both of these oversized options from michael kors. i like the versatility of the resin ($225) — silver and clear go with everything! — as well as the timeless appeal of the tortoise ($250).