Wearing my pair I purchased from the OP today. Fit is great. Very similar to J Crew Urban Slim Fit. Slim in the thigh with a tapered ankle (but not too tapered or awkward). I think they are definitely TTS I would not size up.
Have you looked at Michele? Its a fashion brand (Quartz.. yeck), but girls seem to really like them and they can be found new for $1000-$2000. I think they fit the bill in terms of styling (large, but not too chunky). They may not have 20 year longevity but it could be a nice solution for now
I see the Stowa Antea is suggested, and I think that just falls outside of Poor Man's Watch IMO ($700+).However, if you are looking for inexpensive, yet quality manual wind watches look at Chinese mechanical watches from Sea-Gull, Parnis, or Alpha. Good value, and inexpensive