I loved this post on Blogher by Susan Wagner, and completely agree with her. You don't have to be a size 3 and in your twenties to wear skinny jeans. Don't believe me? Click on this link, and check out her post and picture...she is rocking those jeans! I think she looks great, tasteful and age appropriate.
If you can think of jeans as a type of leggings or tights to wear with a longer tunic, blouse or sweater, then it may be less intimidating to wear them. I've seen them worn with a dress and a ballet flat, and they look great!
If you own a pair of boots, whether fancy knee high boots, winter snow boots or clunky Ugg boots, you will for sure appreciate a skinny jean. There is nothing worst than trying to stuff wide leg jeans into boots, you end up looking short and frumpy. It is hard to find a jean wide-legged enough to fit over boots, and really it defeats the whole purpose of buying a great boot if you are just gonna cover them up with your jeans.
As Susan says, it is all in the fit and proportion, if you can get them to fit well in the hip and thigh, find a great shirt or sweater to balance out the narrow leg, you may be pleasantly surprised at what a great look it is! Check out these Miribelle Dark Wash Skinny Jeans, in plus size. They have a reputation of being comfortable and stretchy. Put a great tunic that hits at the hip bone, throw on so heels, and have a night out on the town!