1) Casual dress/one piece
I'm sure we are all allowed to wear a dress, even you're not going out to dinner or something. Cute statement dress can already make yourself pretty. Wear cardigans if it makes you chilly. Same with rompers/one piece. I think it's a lot easier to pick an outfit with this because you don't have to worry about the bottom because it comes in one! LOL The only con about wearing romper is when you need to go to a bathroom.
2) Colored jeans
Yes, I said it, JEANS, but I mean jeans with different colors other than the default blue (or black). Trousers works too. I wear colored jeans a lot. It just gives a whole different view to my outfit, depending on what color of jeans I'm wearing. My philosophy with colors is that God created colors, and for us to see the colors instead of B&W.... why not enjoy it? By the way, if you're concerned with curvy bottom (like me!) wear a jacket or loose shirt to cover your bottom to balance it out. If you wear heals, that's another plus!
Sometimes, it's hard to wear skirt if you live in super cold climate area (like here in Illinois). If that's the case, good legging with help out a lot. If that won't help, you can totally wear it with another socks/leg warmer over the tights/legging, then wear boots with it. Speaking of skirt, my recent favorite is maxi skirt. I just purchased a nice maxi skirt from Victoria's Secret and it's awesome! It's so comfy! With maxi skirt, you should have no problem wearing legging underneath to warm up during the winter... because usually, people can't see the underneath. :) Also there are tons of skirts to experience to see the one that fits you... pencil, A-line, midi, pleated.... For those who have curvaceous bottom, high waisted A-line supposed to be flattering.
I do wear shorts in winter too, with tights and boots of course! I know there are denim shorts but it's fun to pick out pair of shorts with different materials.
On a lighter note, here are some good fashion blogs I check with occasionally. They are filled with very inspiring outfits, style tips, and deals!
http://www.extrapetite.com/ - For those who are petite....
http://www.thechloeconspiracy.com/ - she posts out some deals and coupon codes occasionally... AND her outfits are fabulous!
http://www.iamchiconthecheap.com/ - affordable, but staying chic!
p.s. - those images aren't mine, I searched through google so credits goes to whoever posted originally.