When I first started commuting by bike to work, I was wearing mesh shorts and t-shirts. It was five miles to the train station, then another mile and a half to work from the back end of the train ride. My butt could take it.
But as I rode more, I realized I needed shorts. So I went out and got some mountain bike shorts with a second short underneath with padding. Obviously, I was a little hesitant to look like all the other SoCal cyclists and their stretchy pants.
As the weather got cold, I fashioned some leg warmers out of a pair of old tights that Emmy's mom gave her to give to me because they didn't fit. (I'm very resourceful, I think I get that from Grandma.)
Me in old bike shorts:
Well, little did I know the wheels were in motion for my general improvement. Emmy decides I look silly and gets me some real bike shorts and leg warmers for Christmas. Boy is it easier riding with those.
Me with new bike shorts:

But the best part of the story? Better gear meant more riding. More riding (coupled with the training for the half-marathon) meant better bike fitness. And all that led to... (drum-roll please!)
Me beating Toby and Airey in the February TCSD Duathlon!!!* Hahahaha suckers!!! Better luck next time. Watch out if I get some arm warmers!
*OK, so they got lost on the bike route and traveled way out of their way, but still. My intelligence won the day.