You can't go wrong with a comfy pullover cashmere sweater and leather leggings. Sometimes when I just want to be comfortable and too lazy to plan an outfit, I go back to my favorite color palette (black and white) and put some booties on to dress it up.
sweater - madewell | booties - steve madden | leather leggings - target (similar here)
bucket bag - sole society (similar here)
photos by justfeng