Answer: Chrysanthemums, ornamental kale, primroses or pansies would work well for fall color in a window box and with a little luck, would survive the winter to bloom again in the spring. Windowboxes hold so little soil that the roots are nowhere near as well insulated from cold as they would be in the ground, so that is why they may not survive. In a larger container in a sheltered location, they would be more likely to live over the winter. You could also try some of the fancier forms of English ivy, these may be variegated or have ornate shaped foliage and can be quite attractive. The same caveat would however apply.
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