16 Winter Date Outfit Ideas 2021 What To Wear: On A Winter Date
Summer of 2020 I began a series on my website where I share an outfit idea for sixteen different date ideas. The series quickly became one of the most popular on my site and is without a doubt my most requested blog post each season. I intended on getting this blog post up before Christmas but life got crazy—regardless, there are still a couple of more months left of winter and all kinds of festive cheer in the air.
For that reason, I figured it would still be helpful to share an outfit for your most requested winter activities. Don’t forget, feeling comfortable and confident in what you’re wearing is key. I hope this post gives you some outfit inspiration for your next date or if nothing else, a few date ideas for the winter (even if you are just going with your girls!).
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Ice Skating
I’m personally not a fan of ice skating but I know so many people who love to go this time of year. For a night of ice skating something comfy is key! I highly recommend wearing a pair of leggings so you can easily move around. If you want to look a little more put together reach for a pair of faux leather Spanx—they are hands down my favorite! Up top, I’ve thrown on a cute sweater. Don’t forget to layer a puffer over top for added warmth as it does get chilly on the rink.
As for shoes, reach for something that’s easy to get on and off as you’ll be changing into skates. Plus, thick socks are a must to keep your feet warm.
sweater // leggings // boots // socks
Zoo Lights
Every year my sister heads to the Zoo Lights to see the display and every year she struggles with what to wear. You can never go wrong with jeans and a sweater. This is actually a mock neck sweater vest and it’s one of my favs. Layer a long sleeve bodysuit underneath if you’re looking for an extra layer.
No winter outfit of mine is complete without a fun statement jacket. I love this leather puffer as it spices up an outfit while sticking with the neutrals. In true McKenzie fashion, I popped on a pair of heeled boots in the same color to pull this outfit together.
jacket // sweater // jeans // boots // purse
Movie Marathon
I sure do love a cozy two-piece set. I just snagged this one from SheIn and scored dozens of compliments on it when I wore it last week. This set is a comfy knit, very different from my usual fleece-lined set. I especially love that this top and bottom can easily be mixed and matched so you get three outfits for the price of one! Thrown on slippers for a casual movie night on the couch.
Out To Dinner
trying new restaurants each weekend is my absolute favorite past-time and my ideal first date. Regardless of where you’re headed to eat, this outfit is a safe option all around. You can truly never go wrong with a sweater and jeans. This two-piece sweater is so fun and has a feminine element to it that most sweaters don’t have.
I tucked this into a pair of straight-leg jeans. I’ve been wearing this Express pair nonstop lately and they are the best. Because the pants have a boxier feel to them, a heeled bootie is a must. I wear these black ones all the time. Add a cute black purse to match and you’re good to go! Casual yet still put-together.
sweater // jeans // boots // purse
Nutcracker
The Nutcracker is a tradition for several families in our DC area. I’ve personally never been but I imagine a simple white bodysuit paired with a festive tweed mini skirt would work just fine for the occasion. Of course, I had to pull on my favorite black boots to tie the outfit together. These platform boots have a super chunky heel that is surprisingly very easy to walk in! They give me just the confidence boost I need—perfect for a date night.
bodysuit // scarf // boots // purse
Last-Minute Shopping
I know plenty of you have gift cards burning a hole in your pocket after the holiday… something like this is my go-to for a day of shopping. I always prefer to be in jeans as they are what I wear most days so they’re ideal for trying things on. Light layers + comfy walking shoes are a must as well. These are the Hutch boots from Steve Madden and I swear they are the most versatile shoe. I wear these with practically everything and they never fail!
flannel // sweater // jeans // boots
Work Party
Off to a holiday work party? These green leather pants sure would be a fun piece to break out. I have tons of straight-leg leather pants from SheIn but none fit as well as these do. The quality is great for the price + they are the perfect length on me.
These make such a statement on their own that you can keep the rest of the outfit rather simple. I just tucked a white bodysuit into the bottoms and popped on a white heel with a fun feather toe-box to spice things up. Of course, I had to add my new green velvet purse too. I just snagged this from SheIn and it’s been the perfect purse to carry over the holidays!
bodysuit // pants // heels // purse
Christmas Tree Picking
Of course, the time for Christmas tree picking has passed but for the sake of thousands of you referring back to this post in years to come it only feels right to leave this fit in the mix. I just got this brown leather, sherpa-lined jacket and my gosh is it fantastic. Something about this fit makes me want to plan a Colorado trip ASAP, lol. In the meantime, you can find me wearing it to the tree farm!
I’m keeping things simple with a chunky sweater and jeans. The Hutch boots from Steve Madden are the perfect boot for the occasion, plus a hat to match helps tie this outfit together beautifully!
jacket // sweater // jeans // boots // hat
Family Photos
Perhaps you’re taking professional photos together this holiday season. In that case, an outfit like this is perfect. A mix of neutrals is a never fail but a fun pop of color thrown into the mix helps spice up the outfit. I just grabbed this green suede piece from SheIn and am in love with it. Not only is it super soft but it’s the perfect length to layer with. Don’t forget to add a matching scarf for all the winter feels.
jacket // bodysuit // scarf // jeans // boots
Looking At The Lights
My Tik Tok for you page has convinced me that I needed a puffer vest, so naturally, it was the first thing I added to my cart. They take me right back to my middle school days and yet there’s something I love about the nostalgia. This black puffer was the perfect layering piece over top of a gray hoodie.
No casual fit of mine is complete without my Aerie crossover flares. I wear these nonstop and they truly flatter my figure like no other pants. High-top Converse are the perf shoe to match my three-piece bag. This fit is giving ~sporty chic~ for a walk around the neighborhood to see the lights.
hoodie // vest // pants // sneakers // purse
Holiday Gathering
I loved those green leather pants so much that I had to grab them in blue too! I figured these would be perfect come New Year for a fun pop of color. For a night out, I’d wear them with a v-neck bodysuit, preferably the Express Body Contour line, and white feather-toed heels. To keep the shoulders warm feel free to use a scarf as a shawl!
bodysuit // pants // heels // scarf // purse
New Years Eve
New Year’s Eve is right around the corner. I actually published a blog post with ten different outfit ideas already but I figured one more in this blog post wouldn’t hurt. You can’t go wrong with a little black dress for the big night! This one is entirely sequined with a high-leg slit along one side. I love the scoop open back too! While this would look adorable with heels, there’s something I love about a pair of sock boots this time of year.
Winter Wedding
Winter weddings are happening left and right! This emerald green dress is absolutely perfect for your next one. This jersey material is incredibly flattering, accentuating every curve + really flattering the tush. Plus, a cowl neckline never goes out of style. Because this dress is a midi, it looks especially good with a pair of lace-up heels. I’ve been wearing these clear ones nonstop lately and they are the best!
I’m using that same scarf from before as a shawl + adding a green purse to match! I know the colors look a little off on camera but they match beautifully in person!
dress // heels // purse // scarf
Out For Drinks
Meeting up with friends for the first time since high school? Perhaps you’re grabbing drinks and want to look like the successful girlfriend you are. In that case, stick to jeans to make it look like you aren’t trying too hard. But, don’t be afraid to reach for a plunging bodysuit + matching purse to give that sophisticated, polished look. I’d personally go for heels however if they aren’t your jam, boots would do just fine!
bodysuit // jeans // heels // purse
Out On The Town
I know our “going out” scene is rather chill where I live but perhaps you’re headed into the city for a night out on the town. In that case, go big or go home with a body chain top and shiny suit pants. I wear these Princess Polly bottoms all the time as they go with literally everything! Slip into a clear heel to match but don’t forget bandaids as they get incredibly uncomfortable after hours of dancing.
Hot Cocoa/Coffe Date
Nothing like a good coffee date to reconnect with someone! In that case, I’d keep things super casual. Leather leggings will add a little spice without trying too hard. For the top half, go for a white basic tee and a shacket over top. I have this one in several colors and it’s one of my favorite layering pieces in the winter. High-top sneaks and matching socks complete this outfit perfectly!
top // bodysuit // leggings // sneakers // purse
pin this post to refer back to before your big outing!
Phew, sixteen outfits just like that! I love putting together these mirror-style blog posts and hope you enjoy them just as much. While I don’t have any winter dates planned yet, I sure do have an outfit ready for when the time comes, lol. Be sure to stick around as I’ll be back in the springtime for a new installment to my Date Ideas series. Until then… ciao!
With love, McKenz
Latest Post: 10 Outfits To Wear This New Years Eve
Related Post: 16 Winter Date Outfit Ideas 2020
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