Best Winter Date Night Outfit Ideas

Getting motivated to go out when the temperatures drop or when the weather is blustery can be difficult. But there’s so much that winter offers that it would be a shame to miss it all just because Old Man Winter has arrived. Whether it’s eating at a great restaurant, seeing a show, cheering on your local team, or anything else you enjoy doing on date nights, you can stay warm and look stylish even on the coldest nights.

So make an excuse to get out of your women’s loungewear, no matter how comfy it is, and treat yourself to a night out in style with some of our favorite winter date night ideas.

Great-Fitting Jeans and a T-Shirt

Let’s ease into things by starting with a comfortable, warm, versatile option that you might wear on any weekend for running errands. Just because it’s your go-to outfit doesn’t mean you can’t elevate the look with a few trusty tips and tools. Take the ever-so-trendy high-waisted women’s jeans and a basic long-sleeved T-shirt, for example. You might wear that combo with some sneakers on a typical day, but on date night, you can pair it with some cute leather booties, ankle boots, or even pumps. Add some jewelry and a belt, and you’ve taken it to a new level. It’s great for layering as well since you can add a sweater or fashion scarf to make it look like a brand-new outfit. Especially for outdoor events like winter farmers’ markets and sporting events, this is a great date-night outfit when you want to keep things casual but comfortable.

Leggings and a Sweater Dress

This pairing is incredibly comfortable and warm enough for even the coldest nights. Like jeans and a T-shirt, a sweater dress with women's leggings is excellent for casual date nights. But it is so versatile that it can be worn for more formal dates like plays and fancy restaurants as well. A more snug-fit sweater dress has a tendency to look more formal than a baggy sweater dress, but it’s all in how you wear it. Even a loose sweater dress can be belted when you want it to be more form-fitting. Some knee-high or calf-length leather boots elevate the look as well. But you can also wear this outfit with flats or heels, albeit sacrificing a bit of warmth.

A Cashmere Turtleneck and Leather Skirt

Cashmere is like a warm, soft hug during wintertime. And it’s so soft that your date will probably want to hug you in it as well. Since it’s such an indulgent fabric that has an elite status associated with it, it has a way of looking dressed up without even trying. It’s also versatile enough to wear with jeans, skirts, and dress pants. One great way to wear cashmere turtlenecks is to pair them with a contrasting type of material. Leather pants or a leather skirt, for example, can look amazing worn with cashmere on date nights. But some basic dress pants play the part as well. This winter, fun patterns and prints are in style, so have fun mixing and matching your pants with a solid-colored cashmere turtleneck.

A Blouse and Dress Pants

If your date night happens to fall on a Friday, you may not want to go home after work and go back out again. Sometimes it’s easier to meet your date out straight from the office. But you’ll need an outfit that can play the part of a professional outfit and a date night outfit. A cute blouse with some dress pants is a safe choice for this reason. And if your blouse has any details that you don’t feel comfortable wearing at work, you can always hide part of it under a blazer. For example, maybe the arms are lacy, or the back is transparent. Cover it with a blazer during the day, and leave the blazer at the office when you go out. Viola!

Make the Jacket Part of the Outfit

If it isn’t too cold out yet, especially at the beginning and end of winter, you could make your outerwear part of your date-night outfit. Leather jackets are especially great for this reason. Also, a women’s fleece jacket worn with some jeans can look quite nice for casual outdoor events. This is a great choice for cheering on your local football team if you have high-school-aged kids. After all, they can go out with their friends after the game, while you and your date get a bite to eat or catch a movie together. What’s great about fleece is that you can get it in a color that supports your local team and even personalize it with your team’s logo.