The pictures are taken too close up. Give us a view of the whole house and yard from the street.

Yard slopes down to the street.

Window boxes are shallow planters. Most would be under the overhang and require regular hand watering. I would look for black window boxes to match the shutters and I would only use them under the windows with shutters. Plants in pots don't do well in the winter; their roots get colder than if the plant was in the ground. Try winter annuals such as violas, and flowering kale or cabbage. The bay window has an indention between its right side and the porch. I think a shrub might fill in this space, so I placed three in front of this window. To either side of the bay I placed red daylilies; the color duplicates the flower color of the window boxes, and that's the only reason they are red. In front of both the shrubs and perennials is a low edging plant.

I suspect the lack of grass on the right side of the photo is because people walk across the lawn from the driveway to the stairs. People will always take the shortest route, and the only way to stop this is to put something in their way. I added a ground cover shrub to make this shortcut difficult to use.

Choose whatever shrubs suit your needs. Those in front of the bay window can be flowering or not, deciduous or evergreen. Those used to foil the shortcut should be evergreen, but can be broad leaved or coniferous. Use whichever perennials that you like. Daylilies are easy to grow and require little care, though they will die down in colder climates. If you would prefer hostas, or iris, or dwarf hydrangea, use them. The same goes for the edging plant, find a type with color and form you like.

When shopping for plants, check the tags for the expected mature size. If the tag says the plant will grow to 5' tall you may not want to put it under a window. If it will grow 5' wide, it should be planted no closer than 2.5' to a wall or pathway. All new plants will be small. Fill in around them with annuals for the first few years. You don't have to plant everything all at once. Start with the shrubs under the bay window, making sure the bed will be deep enough for their mature size. Before you buy your perennials, make sure to break up the soil and turn in a good amount of compost. You should always have the planting area ready before you buy plants.