Getting dressed in the winter is challenging enough, but getting dressed for a night out? Well, that’s in an entirely separate, far more challenging league of its own. Our natural inclination to meet up for a date feeling sexier than usual is vetoed the second a cold wind hits, begging the question: Without the usual rotation of strappy heels and slinky tops, what does one possibly wear on a winter date?
Look, I don’t know about you, but heading to dinner at the new, trendy spot in town in my run-of-the-mill sweater and jeans isn’t going to cut it. Regardless of whether or not the reservation was easy to book, I want to show up looking and feeling my best, without freezing. That’s why, in recent years, I’ve accumulated a handful of winter date-night staples that are just as confidence-boosting as the ones I wear in warmer weather. Pieces like fitted long-sleeves, sheer tights, and knee-high boots make getting dressed for a winter date a whole lot easier than one might think.
Ahead, I’m sharing six winter date outfit ideas to accommodate any mood or occasion—whether you’re going on a first date or grabbing dinner with your long-term S.O.
For a Mid-Day Coffee
Meeting for coffee is the ultimate low-pressure setting for getting to know someone before moving on to dinner and drinks. Since this is most likely a get-to-know-you date, you’ll still want to put your best, most stylish foot forward—without looking like you’re trying too hard for the daytime. In this instance, I’d suggest your favorite jeans and a quality cardigan, paired with a few jewelry pieces to really tie the look together. For shoes, simple ballet flats or sneakers will do the trick.
To Grab a Late-Night Espresso (Martini)
Thankfully for those of us still wanting to rep a bit of skin this winter, there’s an abundance of see-through mesh and lace pieces to shop that don’t require a bare leg or cold shoulder (well, not entirely). My go-to date night look as of late? A long-sleeve lace top and a black bralette paired with high-waisted jeans and a kitten-heeled boot. Like the inspiration above, I like to drape an oversized blazer over my shoulders for that perfect mix of edgy sophistication with an extra dose of warmth.
For an Afternoon at the Museum
I’m all for a day date. Being able to speak at a normal volume and read the menu flashlight-free? Sign me up. But sometimes, it can be a struggle to turn the casual hangout into something more exciting. That’s when I like to reach for those classic pieces with a twist: an off-the-shoulder sweater, a split-hem pant, or an elevated shoe. Thoughtful details like these read as put-together yet effortless, so even if you did stay up the night before with the first-date jitters picking out the perfect look, no one has to know.
To a Hard-to-Get Dinner Reservation
Something I learned in high school: You can’t control who wins best couple, but you can control who wins best dressed. (I could never find a solid date, but my outfits? My outfits slayed.) So while you may not be able to control the outcome of your date, you can control whether or not you’re wearing an outfit you feel like a 10 in. For that impossible-to-get reservation, you can’t go wrong with a leather accent, which is the perfect companion to toughen up a delicate blouse or a sheer pair of tights.
To a Casual Lunch
Perhaps the best part about a day date is the possibility of a free evening (read: me and my kindle in bed by 9 p.m.). If I’m going to be in my PJs at a reasonable hour, I have no qualms about throwing on a nicer look for lunch. As with a coffee date, I want it to look like I tried, but not too hard. To me, that means a fitted turtleneck, a statement coat, and a relaxed pair of jeans with either a heeled bootie or a chunky loafer. Oh, I can never, ever, forget my staple jewelry and sunnies (yep, even in the winter).
For a Night at the Ballet
I’ll never forget when Carrie wore her infamous pink Oscar de la Renta dress to the ballet in season six of Sex and the City. While I’d love to be able to show up to a viewing of Swan Lake in vintage designer, it’s not exactly within my price range at the moment. Instead, I’ll be channeling Carrie through one of her other most prized possessions: a fur coat. To keep things simple, I’d complete the faux-fur look with knee-high boots and a black mini skirt.
ABOUT THE AUTHOR
Tinsley Crisp, Fashion & Beauty Staff Writer
Tinsley Crisp is a Fashion & Beauty Staff Writer at The Everygirl and specializes in reporting on the season’s latest trends and hottest products. As a New York City-based stylist, she’s committed to injecting joy into the art of getting dressed and delivering attainable yet aspirational content to our readers.
