If there is any highway involved:
Olympia AST hi-viz jacket
Shoei full face helmet
Joe Rocket Ballistic overpants
All of this no matter what the temp is. From 0c to about 15c I wear a liner in the AST and have winter gloves.
From 15c to 30c I STILL wear all the gear, I just open all the ventilation and sweat alot
Local streets in my town:
Cloth 'casual' motorcycle jacket with armour
I have only ridden once without the gloves. I just felt really exposed, as there are no handguards on my 650CS. Rode once in shoes instaed of boots and just didn't feel very comfortable.
On the other hand, I'm a volunteer firefighter and have seen what happens to people who wipe out at even medium speeds, say 40-70km/h. Not pretty and not something I want to experience