16 Winter Date Outfit Ideas

It took me by no surprise when scrolling through my top posts of 2020 to see my summer and fall date night outfit ideas posts ranking highest. This series is hands down the most popular and admittedly, one of my favorites to put together. I can’t say I’m going on any dates myself, but it’s so fun getting to curate different outfit ideas for you all!

With the holidays near and winter right around the corner, I figured now was the right time to sit down and share 16 outfit ideas 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!).

16 Summer Date Outfit Ideas // 16 Fall Date Outfit Ideas

Ice Skating 

Ice skating was by far the most popular winter date you requested outfits for. Admittedly, I’ve only gone once and I hated every second of it. Let’s just say, I’m not super coordinated, especially on ice lol. Nonetheless, I know it’s a super popular winter activity and if I were to ever go again, this is what I’d wear.

I recommend wearing leggings as you’ll be moving around a ton. I have been loving my Spanx this season and the pleather finish is so fun for the holiday time. Most ice rinks are outside which likely means it’ll be chilly. Pop on a puffer coat—these are so trendy right now and this bright red is perfect for this time of year. I added a cute beanie of course. It doesn’t really matter what shoes you wear since you’ll obviously be swapping them out for ice skates!

Outfit Details— jacket: SheIn, top: SheIn, leggings: Spanx, socks: Romwe, shoes: SheIn, hat: CC, earrings: SheIn

Botanical Garden Lights 

I’m so jealous of everyone who has botanical garden lights around them. We have something similar called the Zoo Lights in DC where you get to walk through all of these displays and it’s one of my sister’s favorite holiday dates. I figured this outfit would be super cute for an activity like that!

I’m starting off in a black turtleneck bodysuit. You’ll be seeing this one in several of the outfit ideas today—it’s under $12 and seriously such a staple in my wardrobe. I wear this about once a week and it goes with everything. I tucked mine into a pair of straight-leg jeans. I just got these from SheIn and everything about their fit is to die for. They look amazing with a chunky bootie for some lift. I layered a flannel over top and popped on a cute sherpa bucket hat to keep my ears warm!

Outfit Details— top: SheIn, jeans: SheIn, shoes: Chinese Laundry, flannel: SheIn, hat: SheIn, necklace: The Silver Heron, earrings: SheIn, rings: Ana Luisa

Christmas Tree Picking

I’m sure most of you have picked your Christmas tree out by now but I do know some families who like to save this event for the last second, so I figured I’d go ahead and throw an outfit into the mix. Shackets are going to be your best bet for this outing—not only do they fit the rugged outdoorsy vibe, but they are heavier than your average flannel providing a little extra warmth.

I then threw on a pair of straight-leg jeans. These are new from Express and they are incredibly comfortable. They are full length but I cuffed mine twice and slipped into white chunky sneakers that would be comfy for walking around. Because if you’re anything like my family, this may or may not turn into an all-day adventure lol.

Outfit Details— top: SheIn, jeans: Express, shoes: Ugg, necklace: The Silver Heron, earrings: SheIn, rings: Ana Luisa, watch: Fossil, bracelets: Mantra Band

Movie Marathon

Who doesn’t love a cozy Christmas movie marathon?! I know I’m a fan and love curling up on the couch for the afternoon—even if the endings are far too predictable. This matching sweat set is so comfortable. It’s a cotton rib-knit that is the perfect weight. It’s not too thick and the joggers taper in just enough to keep you from looking frumpy. My Ugg Fluffita slippers have been my go-to’s lately. I wear them around the house and out if I’ve got a quick errand to run!

Outfit Details— sweatshirt: SheIn, joggers: SheIn, shoes: Ugg

Out To Dinner

I’ve got to admit, going out to eat has to be one of my favorite activities. There’s nothing better than catching up with someone over yummy food—date or not! This outfit is very typical for me when eating out. I’m keeping things simple with a solid black bodysuit and some cropped flare jeans. I love the statement sleeves of this one!

To give me a little height (and a confidence boost) I’m reaching for my favorite new boots from SheIn. These patent leather shoes will leave you looking and feeling your best—I promise. Just a few accessories will help take this outfit to the next level. I added a chain bag, simple belt, and gold hoops.

Outfit Details— top: SheIn, jeans: Express, shoes: SheIn, necklace: The Silver Heron, earrings: SheIn, rings: Ana Luisa, watch: Fossil, bracelets: Mantra Band, belt: Romwe, bag: SheIn

Nutcracker

The Nutcracker is one of the most iconic dates of the holiday season. I’ve never been but I know so many couples enjoy a night of music, dancing, or even a play this time of year. More times than not this is a dressier occasion so I highly recommend going for a skirt or dress. I just got this tweed mini skirt so I figured now was the perfect time to style it. I added sheer tights underneath and went with a pair of knee-high boots.

Up top, I’ve got on a cozy sweater. I’ve been so into gold chain necklaces recently and think they add such a classy vibe to your outfit. I layered one overtop of my sweater and then grabbed a quilted crossbody to match.

Outfit Details— sweater: SheIn, skirt: SheIn, tights: Romwe, boots: Steve Madden, earrings: SheIn, bag: SheIn, necklace: SheIn

Last-Minute Shopping 

Last-minute shopping before the holidays is inevitable no matter how hard you try to avoid it. I’ve found a new favorite shopping outfit. Start off in a solid black turtleneck and then layer a sweater vest over top. This one splits up the side and has a super cute hood. The reason I recommend these is that they provide you with a little extra warmth without being overly bulky.

You can easily wear a jacket over top, without having that uncomfortable bunchiness in the arms! I slipped into my new favorite cropped flared jeans from Express and a pair of chunky black boots. This pair from Chinese Laundry is the best for walking as they have a really thick sole and a chunky heel that’s very manageable.

Outfit Details— top: SheIn, sweater: SheIn jeans: Express, shoes: Chinese Laundry, necklace: The Silver Heron, earrings: SheIn, rings: Ana Luisa, watch: Fossil, bracelets: Mantra Band

Work Party

Work parties seem to happen left and right around the holidays and although I’m sure they won’t be as common during this Covid-19 year, I figured I’d still throw this outfit into the mix. Leather pants are the star of this look. This nude pair has the most amazing straight leg fit with a high waist that’s super slimming.

These look awesome with sock booties and mules but for the sake of dressing them up a bit, I reached for a pair of classic block heels. Throw on a statement earring and a gold watch and you’re good to go!

Outfit Details— top: SheIn, bottoms: SheIn, shoes: SheIn, necklace: The Silver Heron, earrings: Express, rings: Ana Luisa, watch: Fossil, bracelets: Mantra Band

Family Photos

I know so many couples who are included in their significant other’s family photos. If you fall under this category then this is the perfect outfit for you! Chances are the family has a set color scheme for their photos—play it safe and go with neutrals so that you don’t clash.

You can’t go wrong with a sweater dress. This one is super family-friendly with endless ways to style it. I’m giving it major points for having pockets. I always love a felt hat for photo occasions and these nude booties match mine perfectly. I added butterfly earrings to spice up the look. Throw on tights if you want to cover your legs; I always love polka dot ones this time of year.

Outfit Details— dress: SheIn, boots: SheIn, hat: Lulus, earrings: SheIn, rings: Ana Luisa

Looking At The Lights

I know we already covered the botanical garden/zoo lights but this outfit is really intended for that “let’s take a walk around the neighborhood and judge which neighbor is more over the top” moment. You know what I mean?! I’m keeping things pretty casual, starting with a solid black tank and a pair of straight-leg jeans. I’ve got on the cutest white hoodie from SheIn. This comes in so many colors and is just the right amount of oversized.

Before heading out the door, pop on a basic puffer. I love the fit of this black one! My shoes are high-top sneakers from Romwe. I love how edgy these are and have been styling them so much these last few weeks. You’ll look effortlessly cool in this outfit combination.

Outfit Details— tank: Boohoo, hoodie: SheIn, jacket: SheIn, jeans: Express, shoes: Romwe, earrings: SheIn, necklace: The Silver Heron, watch: Fossil, bracelets: Mantra Band, rings: Ana Luisa

Holiday Gathering 

Something about the word “party” just doesn’t feel right anymore so perhaps we’ll call it a “gathering” instead, lol. I’m sure there are many families out there still choosing to get together even if it is just kept to family. This outfit is my go-to look for that in-between dress code where you don’t want to look too fancy but you don’t want to be too casual either.

Leather shorts and tights are key. This is such a classy combo and it scores me tons of compliments every time I wear it. Go for a turtleneck sweater in a festive color to keep the holiday cheer present. I front tucked mine and then slipped into a pair of black booties.

Outfit Details— sweater: SheIn, shorts: SheIn, tights: Romwe, shoes: Chinese Laundry, purse: SheIn, earrings: SheIn, rings: Ana Luisa

Holiday Mass

I know so many people who struggle when it comes to choosing an appropriate outfit for church so I decided I’d throw an outfit in for some inspiration. I want to start by saying every church is different; while this outfit would definitely be acceptable where I attend, it may not be for you! The “dress code” varies so much from state to state and even from religion to religion.

I always feel like black on black is a safe bet. This button-up is a business-casual essential and would totally work for church. I paired mine with velvet pants. These are actually leggings but they look so dressy, especially when paired with knee-high boots and a wool coat. This outfit is super classy and yet trendy at the same time! If you’re feeling a little flashy in snakeskin shoes, swap these out for a nude mule instead.

Outfit Details— top: SheIn, leggings: Spanx, jacket: Fashion Nova, shoes: SheIn, earrings: SheIn, necklace: The Silver Heron, watch: Fossil, bracelets: Mantra Band, rings: Ana Luisa

Winter Wedding

Winter wedding season is popping right now especially after so many summer weddings being postponed due to Covid. When I saw this bright red bodycon I knew it’d be perfect for the occasion— I mean come on; does it get any more festive than this?! Plus, one-shoulder details are flattering on so many body shapes.

I’m pairing this cutie with my favorite nude lace-up heels and that same crossbody from earlier. A bold statement earring and a few rings are all this outfit needs to finish it off.

Outfit Details— dress: SheIn, heels: Lulus, earrings: SheIn, purse: SheIn, necklace: The Silver Heron, rings: Ana Luisa

Gingerbread Houses

I’ve seen an influx of gingerbread house competitions happening this year and I’ve got to admit, I do love voting in the Instagram story polls! Just a solid black top and joggers will work for this laid-back activity. I just got these bottoms and they are hands down my new favorite joggers. They aren’t super oversized so you look very polished even in sweats. Adding slippers for good measure.

Outfit Details— top: SheIn, joggers: SheIn, shoes: Ugg, earrings: SheIn

Out On The Town 

Sometimes you’ve just got to grab your bestie and go out on the town—even if it just means walking around and popping into cute small businesses! I decided something edgy for this would be super fun! I’m layering the coolest leather coat over top of a solid white hoodie. I love this sherpa lining and the coat has really deep pockets which I always appreciate.

I’m wearing solid black skinny jeans and dressing things up with a white heeled bootie. Accessories are key here— I went for a black crossbody purse (this is my current fav) and a pair of square sunnies.

Outfit Details— sweatshirt: Boohoo, jacket: SheIn, jeans: Express, shoes: SheIn, earrings: SheIn, sunglasses: SheIn, purse: SheIn

Hot Cocoa/Coffe Date 

Sweater vests baby—I’ve finally hopped on the bandwagon! I mean this outfit looks straight out of the 90s in the best way possible. Pop one on over a solid black turtleneck and front tuck it into your straight leg jeans. A pair of chunky black booties and a baguette bag are all you need to finish off this look. It’s casual yet cute making it perfect for that quick hot cocoa date.

Outfit Details— top: SheIn, sweater: SheIn, jeans: SheIn, shoes: Chinese Laundry, purse: SheIn, earrings: SheIn, watch: Fossil, bracelets: Mantra Band, rings: Ana Luisa

pin this post to refer back to before your big outing!

These posts have quickly become some of your favorites which makes me so happy. I will be sure to keep this series going with another installment come spring! Be sure to DM me photos on Instagram if you choose to recreate any of these outfit ideas yourself. I hope you found this post helpful and that it gave you some outfit inspiration. Let me know what else you need help styling this season!

With love, McKenz

Latest Post: Weekly Wrap Up #50 2020
Related Post: 16 Fall Date Outfit Ideas
Instagram: styledbymckenz // YouTube: McKenzie Morgan // Pinterest: mckenzmorgan