Picking out what to wear for date night is already hard enough. Winter ups the ante on that challenge because you still want to feel good and look cute without compromising warmth. No matter the occasion—a first date or a big anniversary—the best date night outfits are those that make you feel and look good. That doesn’t have to exclusively mean a stiletto and dress.
Ahead, an assortment of winter date night outfit ideas to impress in any situation, from dinner to a cozy movie night. Through styling methods and versatile pieces, you can bring the best of your personal style without performing it. Keep scrolling to discover what to wear with a snazzy coat, how to dress up your favorite pair of jeans, and more.
Colorful Sweater + Boots
A sweater dress (or a chunky knit set) is a fashionable problem-solver in the winter, and they can help bring a feminine flair for date night when styled right. Opt for one with texture or color, and pick accessories to bring energy that’s unique to you. Leather knee-high boots juxtapose nicely against the knit, while also providing coverage and warmth.
Leather Jacket + Baggy Jeans + Statement Hat
There are height gap, there are age gap relationships, and then, there are swag gap relationships. If you want to assert sartorial dominance this winter, look to a smart and swaggy mix of layering that doesn’t over-rely on highly feminine clothes. Think: a trapper hat, loose bottoms, and a powerful silhouette up top.
Off-the-Shoulder Sweater + Silky Skirt + Kitten Heels
It’s easy to explore a little sensuality on date night with a lingerie-inspired, lace-accented silky skirt and an oversized off-the-shoulder sweater up top. A cheeky choker necklace doesn't hurt either.
Also available in extended sizes.
Blazer + T-Shirt + Trousers
Let’s face it: Time is often not on your side for date night. When you have to go straight from the office into a little romance, lean on a classic base with playful accessories. Instead of the usual black or blue trousers, choose winter white pants, then add an oversized blazer on top. Toy with texture in add-ons, like a fuzzy fringe scarf and smooth bucket hat.
Faux Fur Coat + LBD + Patent Heels
Why hold back on date night? Channel someone as extravagant and fabulous as Dynasty’s iconic Dominique Deveraux, and opt for a luxuriously long floor-length faux fur coat to embody the lavish look. A knit dress and heels will complete this outfit, ideal for swanky dinner reservations or nights of culture.
Monochromatic Bomber Jacket + Knit Skirt + Lug-Sole Boots
If pink and red feel played out for date night, especially big nights like Valentine’s Day, look to their more mature (and trending) counterpart: burgundy. It can still stimulate some of the psychological effects of the color red, like passion and luxury. Commit to a monochromatic look in the subdued hue, playing with different textures while staying cozy.
Furry-Trim Jacket + Slouchy Jeans
Few fabrics are as versatile and comfortable as denim, which makes them a great option for date night. For a cool-girl vibe, spice up your favorite wide-leg jeans with a statement-making jacket with a furry trim and low-heeled boots. This outfit combo is best for a more casual or adventurous cold-weather link-up.
See-Through Lace + Wool Coat
The best part about the all-black outfit formula is that there are infinite ways to tweak and tailor it to your style and the occasion. For a winter date night outfit, think about mixing materials and textures, pairing a classic wool coat with a sheer lace bottom and patent leather slingbacks. A turtleneck up top keeps an air of elegance (and keeps you warm).
Patent Trench Coat + Leather Boots
A great statement coat is important in the winter date night outfit equation, and some materials will make a greater impression than others. Try a bold patent trench with smooth leather boots to contrast the shiny outerwear, and a small puffy purse.
