Taking Calvin for a ride would fall in the "justifiable homicide" area. Not on the table. The bike is for me and me alone (well, unless somebody wants to ride b*tch...but I have standards
).
For boots, look at the Triumph Tri Tech. They are reasonably priced and not boy-racer style. Waterproof and pretty tough. That being said, I'm going to buy a pair of Sidis for the track.
For a jacket, textile is great, although if I had it to do over again I would get a good perforated leather one, since I'm going to end up buying a second set or riding gear that I can take on the track. But if you're not going to hit the track, textile is fine and likely cooler.