Dressing for date night during the winter months is tricky if you live in places where weather actually happens. I am speaking from experience, because I grew up mostly in Southern California, where it does not. I could have worn the exact same outfit to prom if it had taken place in June or January (perhaps with the addition of a tastefully coordinated pashmina in the latter case).
Not so much in the nation’s capital, or pretty much anywhere in the Northeast, where I currently reside. So what’s a girl to do when the forecasted temperature is the same as or lower than the proof of alcohol that she intends to drink later that night?
Here’s how I handle the winter dressing conundrum. Obviously, if I am just going from my house, to a car, to the front door of my destination, the only thing I really have to consider is my outerwear. I will make sure that it’s warm and coordinates, both in terms of color and style, with whatever I am wearing.
Please note: outerwear has levels of formality, and they generally don’t mix. For example, no snow-day puffers with cocktail dresses, unless said puffer is long and decorated with feathers and/or fur (you think I’m kidding? I own one of each), or you are Rihanna.
It’s a different story if I know I am going to be walking outside. In the winter, when weather conditions tend to be really bad (rain or snow), choosing the right shoes is essential. You don’t want to be the one complaining, lagging behind, or worse: ruining a good pair.
My “lousy winter weather” shoe roster includes mostly boots or booties with thick versus thin heels, wedge sneakers, and the occasional “I have a newer pair of the exact same ones so I don’t really care” heels. Once I know which shoes I will be wearing, getting dressed is easy.
I tend to stick with pants that I can tuck into my boots (skinny jeans and/or leather leggings) or boyfriend jeans that I can roll to the ankle, because I loathe wet pant hems. If I’m going somewhere on the fancy side, I might pair them with a chic blazer, a cashmere turtleneck or printed silk blouse, and a statement piece of jewelry (bracelet, necklace, but not both). If I’m feeling my inner femme fatale, I’ll wear one of my favorite winter looks, which is a fitted sweater and a long pencil skirt with patterned tights and heels or booties.
But I have to admit that in winter, my favorite is the extreme, “it’s a blizzard so I can’t even” situation. Expectations tend to be lower, so flat, beaten-up leather and rubber shoes are not only acceptable, but advisable (except, that is, by my husband who is literally a foot taller than me and a total shoe snob…whatevs).
Comfy, casual attire is de rigeur. I think of it as toddler chic, because it’s a lot like how I used to dress mine to go outside and play in the winter. I love piling on beanies with pompoms and scarves as big as blankets over my favorite wool fisherman turtleneck sweater, and shoving my feet into my furry snow boots. It’s the closest thing a grown woman can get to a time machine.
Of course, the other option on a cold winter night is just to light a fire, put on your favorite sweatpants and slippers, warm up some soup and pop open a bottle of wine. Hearing the wind outside as I write this, I think that date may be in our forecast.