Ok this one then

Check out the First Ascent line from Eddie Bauer

https://www.eddiebauer.com/EB/First-A...-_-firstascent

Their jackets are very form fitting/flexible, thin but warm - active fit. I have everything from their 600 fill goose down vests and jackets all the way to the outer shell. I use the sandstone jacket for 40+ temps, basically a windbreaker. Some of their jackets have wide, zippered pit vents which is very convenient. Also comes in bright colors since its mountain gear, if that matters. Keep an eye out for the Black Friday/Cyber Monday sales coming up, hope that helps.

Dry wicking layers first, then a cycling specific shell jacket that breaths in the right places like in front of your shoulders and arm pits. Wind resistant tights of any type you prefer is fine. Under shorts can be anything, I like padded cycling shorts. Wool socks, ski gloves and cover your head under your helmet (very important). All of this can be modified here and there depending on the temperature. I use 2 dry wicking under layers when it's in the 20's and only 1 when it's in the 30's. Other than that its the same everyday for my long commute. I do this because I spend 3 hours per day on the bike in very cold weather.

If your commute is not too long, and changing up when you arrive is an issue, then you don't need anything special like that. Just dress as you would if you were walking there and ride slowly.

There's no need to buy "cycling specific" clothing. I used to commute from Prospect Heights to the Upper West Side in regular clothes, albeit in layers I can peel off along the way. Even in the dead of winter, I would be burning up by the time I got to the Manhattan bridge and would have to take my mid-layer (usually a sweater or hoodie) off and stick it in my pannier. Only "special" accessories I would recommend is a face mask/baclava and Goggles. Keeping your head warm goes a long way.

Good looking gear. The two above TOGETHER, could provide warmth up top. that would be coupled with a couple layers of thermal underwear. The bottom and the feet would have to have the same intensity as the top, along with the hands and feet.. We are talking about cold weather here.. Not 50 and 40 degrees.. We are talking about 15 to 25 degrees or colder, that is cold weather. And most likely when dressed for those cold temps, the dress will not be stylish!

Luck, and warm riding to you,

How far is your commute? How much on segregated paths/lanes and how much in traffic?

In NYC your big enemy is wind so you want a good windbreaker up top and sometimes on the bottom. Most days when it's below about 30f I wear pretty much my regular clothes and believe strongly in KISS; sneakers, smartwool socks, jeans, UA base layer top, cotton mock turtle (lands end), sweater (depending on how cold it is), columbia ski jacket, good scarf, gloves, glasses (maui jims if sunny, tifossi yellow if overcast/night). I always carry an insulated headband for my ears (Dale or Columbia) though don't always wear it. If it's really cold I'll wear a ski hat (Columbia insulated) and I have some windbreaker pants I'll pull on over my jeans if it's really bad out.

The balaclava's a good idea. I just pull by scarf up over my face, but a balaclava would be better. I've also been known to stick a baggy over my toes before putting on my shoes.

Be careful not to let yourself overheat and sweat. You should be pretty cool starting out. As you warm up (Brooklyn or Manhattan bridge?), don't hesitate to unzip your jacket or pull your hat off for a bit.

One more thing. Keep notes for a while. Write down exactly what you wear, what temp/wind/sun/precip is when you leave and arrive, and how you felt on the ride. This will help you get to know your body and how you react. It'll also come in handy next year about this time.