Being right near Connecticut, it is nice to take the helmet off for a ride through the lovely roads they have there.
Around town, While riding a CT90 or other sub 100cc bike, I'll wear a bucket (non DOT helmet). Those rides are usually under five minutes and consist of going to get bagels and coffee. There is no or little traffic at those times.
Commuting to Manhattan on my 2010 Fatboy, I used to wear the bucket, but because I didn't want to get stopped by the NYC gestapo and get a 250 dollar ticket, I use my DOT half helmet. I also use that helmet for all fair weather riding, often with ear plugs or earphones (2 Earphones is illegal in NY, one is OK), The decrease in wind noise is amazing and takes stress out of a long ride. I have come to actually prefer the DOT half helmet over the bucket.
In inclement weather, or for trips where I might catch some rain, I have two Bluetooth full face helmets to choose from. I can actually hear the bikes (2014 Ultra Limited HD) speakers better when wearing a full face (Bluetooth rarely turned on).
For off road, I have a HiVis MX full face helmet. Way lighter than the street helmets. I may actually start to use that helmet on the street (it is DOT approved) during the "Grey" months, as I like the HiVis Yellow. Especially since most of my street bikes are black, the main bike being almost entirely flat black.