You might be able to get away with a less-than-stellar wardrobe in warm weather (jeans and vintage t-shirts, all day, err-day), but winter is less forgiving. There is no hiding from the fashion police during the winter. Layers upon layers of ratty flannel and moth-ball ridden sweaters will reveal you for the hand-me-down wearing fashion failure that you are.
You're only saving grace is how quickly it gets dark. Maybe people won't be able to clearly make out the disastrous Russian nesting doll of an outfit you're wearing. Just kidding, they totally will.