I tend to ignore all season-based clothing rules.
Shorts in winter? Yep. Jeans and a blazer in the summer? Sure. A sundress in the cold? Definitely. All you have to do is adapt the item to the appropriate weather. So, all short summer clothing becomes winter clothing with the addition of tights and a jacket. A pair of boyfriend jeans become a summer staple when worn with sandals and a tank top.
I typically wear this romper in the summer, but to make it winter appropriate, I added tights, knee high boots, a faux-fur jacket, and a wool hat. If you ignore all weather based clothing logic you can easily double the size of your closet.
My jacket is vintage but faux-fur is so in right now that there are plenty of options to buy new as well as old.
Because the romper is so short and the boots are tall, the combination of the two of them has an elongating effect, which I can always use.
My bag is also vintage via my favorite shop in Paris, Chinemachine. Real suede and I practically stole it.
Romper: Free People, similar here
Jacket: vintage, similar here
Boots: Madewell, here
Bag: vintage Vanessa Bruno, similar here
Hat: vintage, similar here