"Getting dressed in the winter is challenging enough, but getting dressed for a night out? Well, that’s in an entirely separate, doubly challenging, league of its own. Our natural inclination to show off a bit of skin, vetoed the second we feel the slightest chill in the air, begs 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. Whether or not the reservation was easy to acquire, I want to show up looking and feeling my best–without freezing. That’s why, in recent years, I’ve accumulated a handful of date-night staples that are just as good as my warm-weather go-tos. 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.
But if you’re the kind that prefers to meet in the daytime (three cheers for being able to speak at a normal decibel level), fear not: There’s a few failsafe ideas in the mix for you, too. Ahead, I’m sharing six winter date outfit ideas to accommodate any mood or occasion–whether meeting with someone for the first time, or reconnecting with someone you’ve been with for a long time.
Six Winter Date Looks
1. 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. In this instance, I’d suggest your most-complimentary jeans and a quality cardi, with a few, everyday jewelry pieces to really tie the look together. For shoes, simple ballet flats or sneakers will do the trick.
2. 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, with high-waisted jeans and a kitten-heeled boot. As shown here, I like to drape an oversized blazer over my shoulders for that perfect mix of edgy sophistication and an extra dose of warmth.
3. 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 oftentimes, 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 first-date-jitters–picking out the perfect look–no one has to know.
4. 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 outfit? My outfit slayed.) So while you may not be able to control the outcome of your date, you can control whether or not you have a fire outfit. These days, you can’t go wrong with a swatch of leather: the perfect companion to toughen up a delicate blouse or a sheer set of tights.
5. 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.). So 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).
6. A Night at the Ballet
I’ll never forget when Carrie wore the infamous pink, fitted-waist 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 a knee-high boot and a black mini.
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.