Well you're not going to get more hip than Brooklyn! Williamsburg has always been the heart of hipsterdom, but it's gentrified quite a bit over the years as Wall Street types have swarmed in to buy condos. But it's still interested and has lots of cool stuff to see.
Having said that, if it's your first time to NYC, you're probably better off in Manhattan, and just make a trip out to Williamsburg/Greenpoint. If you can, go on a weekend and check out this
https://www.smorgasburg.com. Also, I recommend taking a the NYC Ferry at some point to get across the river. It's like a really cheap river cruise...although perhaps not as fun in the winter.
Don't worry about "symbolizing gentrification", NY is home to all kinds of people and its constantly changing. The only thing you should be worried about is not being one of those dweebs who walk backwards while taking a photo.