Hi Caprice. Congrats on the new bike. It sounds like you're having lots of fun already.

Regarding tights and capris over shorts, yes they go over spandex bike shorts. I suspect regular, looser shorts would get too bunched up under tights. Another option for keeping your legs warm with bike shorts is to wear leg warmers or knee warmers, like this:

http://www.teamestrogen.com/product/...1-c55-c57.html

http://www.teamestrogen.com/product/...1-c55-c58.html

But if you're not into buying special bike clothing or you want to ride more before deciding what to buy, you can always wear regular sweat pants or any comfortable pants. Just make sure they don't get caught in your chain -- sweats that are snug around the ankles or putting something around your right ankle to keep the pants leg tight should work. Ankle bands like this are good because they're also reflective to make you more visible:

http://www.teamestrogen.com/prodNN_2020N.html

As for petite clothing, I don't know much about that. It looks like Team Estrogen sells some petite apparel. Hopefully some other folks can chime in on other sources.

Regarding carrying stuff, there are all kinds of bags and carriers available for carrying things when you don't have any pockets or your pockets are full. Seat wedges that attach under the back of your saddle come in various sizes. Handlebar bags can also be good. You might want to ask your husband, daughter and son-in-law if they have any spare bags that you can use. If they're anything like me, they've got one or two old ones lying around that just weren't the right size or otherwise needed to be replaced for one reason or another.

Good luck!