It's more about the size, to me. Richard Mille's designs are nicer, IMO, especially compared to Hublot.
I might be a business owner now, but I'm not exactly conservative. I've got tattoos, long hair, never wear a suit, and still play in bands in Los Angeles. LOL
Ultimately, I think this shows the larger point. Wearables are difficult, because everyone's tastes vary so dramatically. I actually think the Apple Watch is somewhat anonymous, and, while it doesn't jump out at me as the greatest design I've ever seen, it doesn't offend me, either. I'd wear one, and I wouldn't say it looks like it was designed by a student. It looks more like it was designed my Marc Newson, for better or worse.