I would concentrate my efforts on the foundation beneath the windows. It appears that there are no planting beds there, if so, maybe buy two long trough planters for those two areas to soften the facade. No, hanging baskets are not “ dated”, but I wouldn’t put them on your house. And, btw, can the trash receptacles be hidden or moved? Get suggestions from your local nursery for appropriate plants & flowers. An independent nursery is an excellent resource.

The only time I think they look "dated" is when they've been left untended and all that's in the basket is the dead stems of what used to be there. I agree with K Laurence, focus on the foundation plantings.

Hanging baskets aren't dated, no. I loved the idea of a long planter for underneath your window, but I don't think I would combine that with the planters flanking your door. If you stick with the pots flanking your door (which are a lovely idea also) then I think I would do a hanging basket on either side of the window. As for what to put in the pots....expert advice (which I cannot offer) is always a good idea. I would suggest sticking with greenery for the planters flanking your door; I like the idea of something tall and sculptural, or large and very full. I would go for some sort of combination (flowers and trailing greenery) for the baskets to soften your home's exterior. Colours are up to you, but I don't think you need to go crazy. The greens alone will 'pop' against your brick. I also agree that it would be nice if you could move or camouflage your bins.

I think something similar to these trough planters would look lovely under your windows.....

i wouldnt call hanging baskets 'dated', rather 'old timey'. they kinds of porches i see them hanging on all have a certain victorian type style.... regardless of when the house was built.

get your planters going (its already august....) and then decide if you need 'more' before buying the baskets and plants.

No, you're not wrong, they're dated. I would get two very large oversized black urns for either side of the front door and fill those.