Watches are one of the 5 key accessories that everyone should invest in to make a good impression - in business and in life - the others being: wallet (for men and women), purse, sunglasses, a pen and, of course, shoes. Even if you wear them everyday, if they are a classic style and decent quality, any outfit will be elevated.
I know there are people out there that collect and buy watches like candy, and while I can understand the lure of the watch wardrobe, I've never fallen prey to it myself. I typically wear only one or two watches. I wear a diamond bezel Raymond Weil most every day, but I want to have a more casual watch that is still classy looking. For a sport watch, I like a men's-sized face and wear it loose like a bracelet. My favorite so far is this watch by Toy Watch bought at Neiman Marcus. It's acrylic and has a mother-of-pearl face with crystals at each number. It has a great style and even has a built in stopwatch.
This watch comes in a number of color combinations and faces, but I think if I had not bought the one above I would buy the orange-faced model. I'm loving orange accessories.
The acrylic watches are about $250, so not much more than a Fossil watch. If I had an extra grand to throw around, I would get this ceramic version. It's pretty frickin' cool.
People notice the details, so it makes sense to have your casual accessories be just as stylish as your nicer watch. And make sure to wear your nice watch, not just save it for a "special occasion". Those events are typically few and far between. You're worth your nice stuff every day.