Yeah, it's hard in the beginning. But as you accumulate more proper clothing and gear over time, it gets easier. This is my second Winter and I'm definitely more comfortable and better prepared than the last one. I have at least two of everything down to Sealskinz socks. I expect following Winters to be even easier. Man, I'd love a Pugsley with studded Endomorph tires for Winter!!! Although, Winters in NYC aren't usually as snowy as this Winter.