Is anybody worth freezing your butt off for on a first date? The answer is debatable, and that's what makes figuring out what to wear on a first date when it's cold a fashion challenge of Herculean proportions. It's a choice between two evils: dress for warmth and risk looking like a mish mosh of thermal fabrics and knitting; or dress for your date in and come home with décolletage so cold you could chill a bottle of wine on it.
Dating is hard enough, with its awkward social niceties and the pressure of making conversation with a stranger for hours, and adding chilly weather to the mix is enough to give even the most seasoned dater a case of cold feet. We've heard all our lives about the importance of making a good first impression (and how to fix a bad one), so picking out an outfit for a first date carries more weight than what you wear to a second or third. In my experience, I always fell back on my favorite staples: a simple black tee and jeans, which are easy to dress up or down for the occasion. When it got cold, I'd switch out the black tee for a black turtleneck. Unoriginal? Maybe, but I always felt confident and comfortable. That's what it all comes down to: figuring out what makes you feel confident and comfortable so you can kick back and enjoy the night.
