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How to wear this outfit in Winter?

I really love this outfit and enjoyed wearing it over the (dismal) summer months. I’d like to continue to wear it, or a variation of it but I’m not quite sure what combination to employ. These are my questions:

Are boots to ‘heavy’ with such a light coloured dress and fabric?
The jacket is too light with short sleeves, but will a trench just cover up the dress?
Would a motorcycle leather jacket be too much?

I’m thinking if I wear it with opaque black tights, stream lined heels, black leather gloves(or, these could be in a complimentary but opposing colour) and either my cropped leather jacket or a trench. Same bag.

My fashion instinct tells me that opaque tights would look silly with these shoes but if you have other thoughts do let me know!