Well "stylish" can mean many things.
Personally, for around $100, I would look at the Seiko 5 series. These are very solid automatic movements (no batteries, but no winding either - if you wear them). They are built well, and there is a lot of variety in the styles available.
For example - an Amazon search for Men's Seiko 5, priced 50-100 provides:
Casio G-shock for work - it's indestructible, not too chunky and has everything I need.
I don't have a dress watch nor the current means to buy one, but I'm interested in some day getting a quality, swiss-made timepiece.
I have worn a watch for so long now that its neither part of my dress or a mere time keeper, it is a part of ME. I feel very odd if I dont have the old Timex strapped on. Plus, Its easier just to glance down and check the time instead of having to dig the phone out of my pocket.