I was having a conversation with one of my colleagues and he said he doesn't wear the jersey or shorts during short rides. I wore one when I went 14 miles and then when I rode back. I suppose for comfort I wouldn't really like a bunch of hanging clothing, and as it was my first road bike ride I didn't want to chafe.

So, when is a ride short enough not to bother with the shorts? Are the undergarment style options worth an investment for a 12 mile commute? Should I just wear the gear and embrace it for what it is?

My commute is 13 miles each way, and I wear the kit every time.

But if I'm on the MUP with my kids for a few miles, I'll just wear athletic shorts, fitted T, and running shoes (with clipless pedals).

I wear bibs and jersey for my 4 mile commute. Its more comfortable especially in the heat

Good point. I feel like it helps the wind do its job. Plus I feel like am a real cyclist like you guys.

For anything longer than 30 minutes, I prefer bibs and a jersey. Plus it saves a lot of wear and tear on your work clothes. For some of us, that means wool dress pants, which are not really designed for daily riding.

If it's hot out, then I kit up. Regular street clothes get sweaty too fast.

If it isn't hot out, then I have been known to ride 20+ miles in street clothes.

I wear shorts and a jersey for just about every ride I do.

Except maybe when I'm travelling/touring. Then I will bring cycling shorts, but I might wear a wicking T-shirt instead.

Am I riding my road bike...kit up.
Am I riding a different bike...wear whatever.

All depends on what my goal is while riding the bike.

Like SpeshulEd - training and recreational rides on the road bike may be longer or shorter, but as such, I always wear the lycra. If I'm taking the bike to run an errand or make a social visit somewhere, I'll wear street clothes, but if the destination is more than 10 miles away, I'll usually wear cycling shorts in lieu of regular underwear.

The only time I'm in just shorts and a t shirt is if I'm riding to the gym and then I'm wearing nikes with clipless pedals too. If I'm riding to be riding, I'm wearing it all.