Winter date nights are a tricky puzzle. You want to look effortlessly stylish, but you also don’t want to spend the evening shivering like an ice sculpture. Because let’s face it—“I’m freezing” isn’t exactly the vibe you want to bring to a romantic evening.

Over the years, I’ve learned some hard lessons about winter layering. Like the time I thought a leather jacket was “warm enough” (it wasn’t) or when I turned into a human marshmallow in an overstuffed puffer coat. These days, I’ve nailed down the art of dressing for the season without sacrificing comfort or style.