Feels like 30 in New York

Temp: 40 with a feels like of 30; mostly sunny
Wind: WINDY! Gusts of 25mph
Precip./Humidity: None/low
Terrain: Mostly flat
Distance: 8 miles

What I wore: knit hat and gloves; light-weight, wind-resistant jacket; light-weight, long-sleeve technical top; compression tights; and a neck gaiter.

Did it work: Yes, although my finger tips were cold around mile 5. Also, my wind-resistant jacket does not allow moisture to escape, so my shirt was very sweaty by the time I got home. This was fine because I could change out of my cold, wet shirt right away but should be considered if you have a drive or long walk at the end of your run.
This weather can be tricky because of the difference in the actual versus feels like temps. When you first step outside, the feels like temp will hit you. Shorter runs won't give you as much time to warm up, so I recommend a heavier top if you're doing a flat run of fewer than 2 miles.

Tip: A neck gaiter or scarf is one of your most important pieces of running gear when temps creep into the 30s and below. I like this one from Powderfish, which has fleece on the outside and wick-away fabric on the inside. The fleece keeps me warm while the wick-away fabric keeps me from developing icicles in my nose. Some more of the benefits of a gaiter are:

• Keeps your neck warm, obviously, which means you're less likely to turtle - pulling your shoulders up around your ears in an effort to stay warm. Turtling will make you tighten up all over. Staying loose in the cold keeps you more comfortable and make cold-weather running more sustainable in the long term. 
• Serves as a wind block. Sometimes, when the wind blows directly into my face, I have a hard time breathing. Tucking my nose and mouth into the gator lets me breathe easy.
• Gives your face cover. There's no need to wear your winter run on your face like a chapped, red badge of courage. When the temps turn icy, protect your skin, including your face.