[Isabo]

A very hard question for me. I got it down to three.
Rolex steel&gold date on jubilee bracelet. Best allrounder for a woman, can be worn on the beach, at a formal event or smart casual, always looks right and is never out of place.
Porsche Chrono (Black) pressy from my husband, with its highspots on the black it goes well with my scruffy 911 and distressed leather bomberjacket and jeans. But it's the thought behind the watch that makes it so special to me.
Franck Muller Casablanca, salmon dial, pigskin strap. Another present from my husband, it has style, status and is supercool!
What to buy for less than $1000? Locman for style on a budget and save up for the one you really want. As Jason suggested above; learn a little bit about different watches and go for the quality brands. Sometimes they are just about fashion and marketing but as long as you are aware of it, it's not a problem. Learn and then buy one you like that you can see yourself wearing for 40 years.