Dress your top half first. Combine a long T-shirt with a camisole or tank top underneath for simple layers. You could also layer a scoop neck shirt under a V-neck tunic sweater for layers that will keep you a little warmer. Add a jacket with lapels for a final warm layer, if you wish.
Slip on the skinnies. Dark denim, black, khakis or white denim -- any color that matches your mood and your other separates would work fine.
Extend your legs with some heels. Choose spike-heeled pumps for a classic look. If you decide to go with boots, any height will do -- above-the-knee, knee-length or ankle boots -- but the higher the heel, the longer your legs will look. Tuck the skinnies inside your boots.
The trick to making skinnies work is to hide your flaws. If you are heavier around the midsection or across your hips, hide this with longer tops that cover these areas, extending to midthigh.
When you're comfortable in your skin, your confidence will shine. Just about any girl with confidence can wear skinnies if she wants to.