I pulled out one of my favorite spring + summer skirts last week when we were in Kiawah and styled it for wintertime (since it was FAH-reezing, but we were still at the beach.)
I swapped my white cami I usually wear it with for a black sweater and dressed it up with my favorite scalloped heels. Especially in the South, I feel like you can get away with bright punchy colors and prints in the wintertime as long as you pair them with something neutral like a solid black sweater.
This black sweater has been on heavy repeat this winter from H&M and is under $20. They always have the best sweaters for such good prices (here are tons of sweater options).
This skirt is old from Nordstrom (Halogen) but I rounded up some other printed skirts that would work great now with a sweater and later with a cami, tank, or tee!