Dressing for date night can be quite the conundrum under normal circumstances, but that increases tenfold in the winter. You want to feel polished and elegant while still remaining comfortable (but also effortless)—it’s a tall order. When you factor in frigid temperatures, the outfit puzzle suddenly feels impossible. 

Enter the pretty top. It’s a classic for a reason, as it pairs well with everything from maxi skirts to tailored trousers. But not just any top will work when you consider the low temperatures and layers of outerwear. I have a system for gauging if a top will work well for those winter nights out: Either it has sleeves, or it has a material or neckline that looks nice under a jacket. As long as it meets one of those criteria, I can rest assured I’ll be comfortable for wherever the evening takes me. Since we’re still in peak winter and approaching Valentine’s Day, I’m highlighting 31 cute winter tops perfect for date night. 


Caitlin Burnett

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