Trendy or not black will match your garage door. Are the bricks cream? Is there cream siding that will be less stark than white?

Our garage door and front door are fairly new, so we won’t be replacing those.

Both are easily painted.

I am worried though, that black windows are a trend

They are. They can look good on some homes, but get used more on ones where they don't belong, like on your house. I'd stick with white for looks and the cost savings.

any advice on the white siding on second floor?

What type of siding is it? Looks like it needs a good wash.

A picture or two taken in daylight would be helpful.

Pretty home. Not sure the modern "trend" of black windows really hits the mark here with the style of your home.

Ultimately...it's yours and make it look how you want. That's who will really be enjoying it, but unless you are changing some other siding colors and modernizing the exterior facade, black windows will look out of place here.

I agree with WoW above ^^^, black will look out of place. I would use white windows.

Take a picture that isn't in shadow. I like the shutters on your house. White seems more versatile to me. White trim is common, black, less so.