I also live in the nyc area and at one time I commuted about 30 miles to brooklyn almost everyday. My rule of thumb back then was not to ride if it was less that 32 degrees. I had these 3 finger gloves that looked like boxing gloves. They did the trick. Layers and ski pants did the rest. But...I would not recommend this to anyone. Its just not worth it . Stay home and look at maps and plan a nice spring trip. The rule of thumb is 50 degrees now. Think about it ...is all that gear really worth it. The winter is only 4 months.