Dead plants are never attractive. Neither are fake ones. And that’s the reality of windowboxes for 95% of folks. No one wants to take the time open the windows to water 2x a day. Or to get out a ladder.

Not a pro- I like your colored front door! I would focus more on your landscaping. How about 2 big white pots on either side of front step with some bight plants? Maybe the landscape experts can recommend something for the area with the brick. Good luck!

I am an avid gardener and have tried window boxes several times. I have had no success.

Window boxes need to be large (not just long) in order to have a big enough root ball to support the blooms, and that means that they are very heavy when they're watered. Also, water tends to drain down the house and stain the siding.

They look great in most drawings but I have seen none in real life that look like that.

how about just taking down the shutters to start.