1. Some early Constellations (the linen dial bumper wind is my daily wear, but I also have some neat pie pans)
2. An Autavia
3. A fantastic full-on 70s Breitling Transocean
4. Revue Thommen Airspeed - not fancy or significant, but the perfect pilot's watch in terms of design.
5. Speedmaster 125 (first automatic chronometer grade chronograph). Look it up. Huge watch; entire time assembly can be removed intact from case. It's like a steel ingot. Made for Omega's 125th anniversary. Mine is mint and was rebuilt by Omega about 12 years ago.
6. Some early cal. 321 Speedmasters
None of these are very blingy or haute horology but they each have particular qualities I like.