We're taking on a cold-weather staple that can be tricky to style: the sweater dress. The first step is finding the right sweater dress: the most important thing is fit — you don’t want it to be too tight and clingy! We chose a dark green version from Club Monaco as the canvas for all of our outfits. Watch on to see how you can style your sweater dress for work, the weekend, and even a night out. On Allison McNamara: Ella Moss top, BCBG Max Azria skirt. Hair and makeup by Kasia Bohos.