Style Guide: How to Wear Dresses When It's Cold Out Lauren Conrad Winter Dresses for the Mom on the Go Healthy By Heather Brown Winter Cocktail Dresses Bloomingdale's Cavosen Going Out Dresses for Women Long Sleeve Beige Knitted Sweater Dress Maxi Wrap Crew Neck Calf Length Long Dress Striped Pullover Warm Casual How To Wear Dresses In The Winter an indigo day Plot twist: even if youre pregnant this winter, dresses are your new best friends! Personally, I like adding tights or knee socks and tall boots when Im going out. , 1. Black Dress @meshki , 2.