Throw a blanket around them and make a run for inside when out and about. DS is usually in weather appropriate clothing (sweater, pants, socks and shoes with a zip up hoodie in colder weather) so I really don't see the need in adding another bulky jacket. It's like 30 seconds in the cold...baby won't freeze to death.
Jogging...same thing...layers and a blanket over the top. If it's raining, drizzling or snowing...rain shield thing snaps over the jogging stroller. DS usually falls asleep while I'm jogging any ways.
Previous rule of thumb (can't remember where I read it...maybe a parenting book?) was if the tops of the head, hands and feet are kept warm you're good! Don't over think it too much!