I will try:
1. An everyday watch
2. A dress watch
3. A sports watch
4. A quirky watch
The first three cover all bases of daily life, and the fourth is really more of a conversation piece, one that has a particular detail or complication or history that makes it special.
In my case, at this particular time, it would look something like this:
1. Omega Speedmaster 3861
2. A.Lange&Soehne 1815 Auf / Ab
3. Rolex Explorer II 16570
4. Vacheron Constantin Historiques Cornes de Vache 1955