I don't really have cycling specific clothing. But to me "gear up" isn't cycling specific. So yes I do gear up before getting on the bike. This morning it was 45°F, a couple of days ago it was 35, a few weeks ago there some days in the 20s, last week there was a morning in the 50s.

Before I get on the bike I check the weather. Even if it is just to look outside. I don't want to wear clothing for the 20s when it is 45, nor a T-shirt in the 40s either. When I was younger I did that a few times. Brrrrrr.

Like others I keep spare clothes at work. Especially in the summer.