"I’ll be honest: I haven’t been on a first date in a while. Being in a four-year relationship has kept the first-date jitters away, yet I can still remember clawing through my closet in a cold sweat to find the best outfit for the occasion. Like they say, first impressions matter, and what you decide to wear on a first date can say a lot about you. The easily attainable goals of a great first date look are as follows: It needs to be memorable, make you feel confident, and, of course, be the best outfit you’ve ever put together in your life. The search for an outfit that captures all of this is what makes the task so stressful—especially if you’re going on a winter first date. The option for heels might be out the window if it’s snowing, but not unless they’re the only shoe that looks good with the dress you’re wearing. Right?
This Baggy Dad style from Levi’s is a tried-and-true favorite our team swears by, made famous by an effortlessly cool fit and PJ-like comfort.
Jokes aside, the best first-date look (or date look, period), particularly in the colder months, isn’t always the most magical and instead is rather straightforward. Building a capsule wardrobe can also ensure you always feel like you have something to wear, whether for a first date or not. Maybe you were invited to have a night out on the town or are simply going on a date to your local coffee shop—no matter what the case may be, we’ve pulled six outfits worth recreating (and organized them by occasion) for your next upcoming winter date.
For a Night Out on the Town
When the weather is cold, a night out on the town hopping from restaurant to bar is difficult to dress for. You can’t ever go wrong with an LBD, and trendy red tights are a perfect flirty, sexy addition to take the look up a notch. Start with a neutral-colored dress as a blank canvas and add personal touches throughout to make the look feel more authentic to you. You’ll feel done up in the best way.
For a Snow Date
The key to dressing for a date in the snow is prioritizing warmth. I know doing so isn’t always the most glamorous, but it will make your date all the more enjoyable. Boots that you know can withstand the weather are essential, and when they’re styled up, can be equal parts practical and cool. Wear an oversized sweater of your choice and layer it with a puffer, and add cute accessories like a beanie or your favorite sunglasses to top it all off. With this cozy look, you’ll be able to focus on the date, rather than how cold you are.
For a Winter Stroll
Meeting for a walk in the park or a drink at your local dive bar? Keep it casual with your favorite pair of sneakers and straight-leg pants. Although the look is slightly minimalist, you’ll feel comfortable, which is what matters most. Currently, my favorite sneakers are the Adidas Spezial (which I predict to take the place of the Samba in 2024.) Style these with straight-leg trousers and a sweater that has a pop of color or cool print. Lastly, layer it over with a coat for warmth. It’s a simple look, but so is the date itself.
For a Casual Coffee Date
A coffee (or hot cocoa) date is as casual as it gets and your outfit should match the date’s energy. Where some feel as though a casual outfit is a boring one, we’re here to prove to you otherwise. Pair your favorite seasonal jacket—maybe it’s a trendy brown bomber or a leather trench—with a simple sweater of your choice and your favorite denim. For shoes, a fun winter clog like a fuzzy or suede Birkenstock can bring life into the look through its interesting texture. You’ll feel comfortable and not overdressed, which can be a much-needed boost of confidence on a first date.
For a Cozy Movie Night
What’s more worthy of a winter date than snuggling up by the fire to watch a movie? The cool weather permits it, and it can be a great way to get to know someone. That said, you can look just as chic for dates indoors, and it starts with great loungewear. This blue knit set is casual, yet still put-together enough to signal that it’s not an ordinary night on the couch. You can wear the top buttoned-up or unbuttoned with a pointelle top layered underneath. Pop on some dainty hoops and fuzzy socks, and you’re ready for your movie date.
For a Dinner Date
The dinner date is, in my opinion, the most fun date to dress for. The opportunities for dressing are endless, which is why it’s just as stressful to get ready for as it is fun. Depending on the ambiance of the restaurant, a faux fur coat can be a cool conversation starter. We know the piece is a little daring, but it adds a rich mom energy to any look that just can’t be beat. Since you’ll likely take off your coat at some point while inside, an off-the-shoulder top is the perfect understated layer that’s also a little flirty. Pair it with baggy jeans and a simple ankle boot. The coat is the statement piece that ties the look together, but you can swap it with an oversized trench, wool coat, or gabardine trench depending on what you have hanging in your closet.
