Hi. I'm no expert (very far from it lol), but in dealing with a situation similar to yours, I came across this video: https://www.youtube.com/watch?v=kUXKXJScyYQ This person added the trim afterwards (on top of the stucco). Doing that might make you feel better about your windows. Good luck going forward. Please let us know what you decided to do. Depending on the shape of the trim you choose, if you try this, you might be able to get close to the look of the window trim in the picture shared by Jeffrey above even though not actually recessed.

"What of its features suggest Italianate, to you?" Low sloped hipped roof. Center wall dormer feature with a jerkenhead clipped gable. Vertical siding with a decorative bottom edge. Large open cornice overhang with brackets. 2/2 windows, not paired, some narrow. Paired entrance door. Bay window design. What's not chacteristic of the Italiante stye is the plain window head trim and the date of construction. The house is bit of a mystery but I would not be looking for Colonial Revival colors. This is the Italiante house across the street from my house:

I have avoided window treatments for the main bedroom in my Tudor house because my husband and I love wood frames and beams. However, I need to add blackouts and see-through treatment because the moonlight affects my sleep. Any advice on what would work? We'd like not to install anything on the wood frame. I posted a picture of the window below.

Definitely not a pro but I am wondering about toning down the white siding and pulling a taupe from the (brick) mortar? and then have the upper shutters very close in color so they add dimension to the windows but with less contrast (I think toning down the high contrast white + black shutters could help get you closer to the look you want) choose gutters that will blend as a much as possible - our horizontal gutters are the trim color and our downspouts are the house body color Does the brick continue around the house?