I know some will jump down my throat for this, but I'd take a look at Rolex, if not to buy, then perhaps for inspiration. To my eye, they make some classic looking dress and sport watches, as long as you avoid the "bling" factor. I've had a simple oyster perpetual datejust for several years now. Stainless steel with a white face and roman numerals. It's simple, understated, runs great, and can be used in both a dress and a casual situation. For sport watches, I've always loved the look of the Rolex Submariner in stainless with a black face (I just bought the Seiko diver copy of this - obviously a completely different price range). Also, IWC has, to my eye, some really classic looking dress watches. Of course, if your fiancee is willing to spend up to $9,000, you should be able to get quite a watch.