Whether it's the first date or the 100th, take this occasion to dress up and make it extra special.

First date, second date, or any in between -- these outfits range from chic and dressy to casual and comfortable to make you feel great on any date you're headed on!

But after the plan is set, the question always remains: What do I wear? And the answer is any of these 28 summer date outfits. Before we dive into the looks, let's talk strategy.

Consider us your sartorial wingmen, then, because we laid out a handful of foolproof winter date night outfits for every type of cold-weather link-up in the books. Learn them, live them, love them ...