Right now all of my favourite dresses are from Old Navy. You can usually find them in the clearance racks ranging in price from $2 - $20. They fit like a glove on me and I love the assortment of styles, colours and materials. Also, I can't really argue with the prices. I also have some from New Look, Avon and of course, thrift shops. If you find it's difficult to find a dress to fit your body type properly, look for something in a jersey-type material. It's usually very forgiving and flatters every body type. Also, a pop of colour can bright shed some light on an otherwise dark winters day.
Here are some outfits I could definitely see myself wearing over the next couple of months. The second one is especially easy, and leggings are much much warmer than pantyhose.
Look One: jacket/ New Look dress/ H&M, clutch/ New Look, necklace/ ASOS, booties/ Jeffrey Campbell via Solestruck, tights/ Addition Elle
Look Two: dress/ Old Navy, leggings/ New Look, blazer/ H&M, boots/ black velvet Dr Martens via Solestruck, necklace/ ASOS, watch/ MBMJ, purse/ H&M
* All images belong to their respective owners and have been referenced back to the original sources. This post was not sponsored or endorsed in any way, all thoughts are my own