Thanks!

Actually, I tend to dress like this for everyday as well (a benefit of being self-employed). I like to wear wool and/or things that let me move and stretch.
I also like being able to hop on my bike into town for errands without changing clothes. If I'm doing a long ride over 10 miles then yes I put on bike shorts with good chamois and usually a good dose of a hi-vis yellow item mixed in somewhere.
In these photos I was wearing my favorite Terry "Spinnaker" knickers (with such a thin cotton chamois that I can wear them for everyday on or off my bike), and a black Smartwool thin merino tank top under the bolero. It was only about 70 degrees yesterday!

Today it started out at 65 when we started riding, to high of 80 by the end- we rode 35 miles/ 3 1/2 hours, so I wore my Brooks Nightlife Hi-vis yellow tank top with the bolero (still showed a nice big screaming yellow portion front and back because the bolero is quite short), and some black bike shorts with a good chamois. The bolero kept my arms from freezing early in the ride, kept me from getting sunburned, and later I just pushed the sleeves up as things warmed up. If I really got hot I could have taken the bolero off and kept my hi-vis tank top on alone. But I never got too hot today.

I probably won't wear the skirts on any long rides, just the bumming around errand rides and also plain daily wear. I will likely wear the skirts to the roller rink too, thus covering over my padded 'crash' shorts with the odd looking tailbone protection and hip protection pads.
Even though it looks somewhat frivolous, this is actually a very practical set of clothes for me.
though I'm used to wearing short skirts with leggings, the whole bolero thing is totally new to me.

Now I am interested in hearing about others' experiences with the Terry boleros....and any pictures of you all in them?