Too Cold for Dresses? These Winter Outfits Will Change Your Mind

It’s 8:15 a.m. You step outside, and within seconds, a rogue gust of wind finds your knees as if it has been searching for them all year. With the right layers below and above, a dress + winter can be BFFs. Consider these cozy (yet chic!) combos inspiration for getting dressed when your legs would like a say in things, but pants are feeling a tad…boring?

1. Gray Sweater Dress, Black Opaque Tights, and Knee-High Boots

If so, fear not! A sweater dress is winter’s version of comfort food. Ours in gray with opaque black tights to keep it sleek instead of slouchy, this ensemble can take you from office to school pickup to a dinner you didn’t even plan on. The knee-high boots are designed to cover the gap between the hem and ankle so the wind has nowhere to play. Camel coat + small gold hoops = looking like you had it all figured out (even if you didn’t).

2. Black Slip Dress, Chunky Cream Turtleneck, and Combat Boots

I bought a slip dress to wear to a wedding this summer, and I am NOT letting her hibernate! Ours in bias cut flirts with our chunky cream turtleneck instead of looking bulky (a true marvel of fashion physics), making it as at home in a bookstore as a bar. Combat boots keep things a tad edgy + slush-resistant, while our long wool coat + minimal jewelry finish things off with an air of I’m-busy-so-my-look-does-the-talking-for-me.

3. Plaid Wool Midi Dress, Brown Tights, and Loafers

Polished enough for meetings + warm enough to actually be warm (thanks to a wool fabric that lives up to its name), this plaid midi is the uniform of every professor we know who’s probably a hoot at parties. Tights in brown instead of black soften things up + flatter the warmer tones found in most plaids, while loafers keep it all grounded enough for working-at-a-desk days when boots are just too much. If your office thermostat is acting up, consider adding a cropped cardigan to the mix. I love that tortoiseshell clip, it keeps things cozy and in the same color family!

4. Knit Midi Dress, Long Camel Coat, and Tall Riding Boots

Sound familiar? Ah, winter weekends in small towns where everyone’s got a great scarf. Our fitted knit midi lends a long, clean line, while our camel coat lends a bit of movie magic (even when we’re just, you know, getting groceries). Riding boots are tall enough to disappear beneath the hemline (hello, legs!), making this our go-to for brunch dates, holiday shopping, + visiting the in-laws (minus the trying-too-hard part). A plaid blanket scarf to finish off the look, and a coffee you’ll forget to drink while it’s still hot.

5. Velvet Wrap Dress, Sheer Black Tights, and Block Heel Pumps

Who says dresses are just for nights out? Velvet dresses are the outfits version of candlelight. Our wrap version in burgundy (or green!) is ideal for date nights, holiday parties, + any December dinner party where you sense people will be dressing up a tad more than usual. Bonus: The wrap style skims the figure instead of clinging to it, which is a Godsend after the second round of passed hors d’oeuvres.

Sheer black tights keep it elegant while adding a layer of warmth, and block heels mean you can actually stand at the party for three hours. We like styling ours with a tailored black coat or a glammy faux fur stole, depending on our mood.

6. Turtleneck Sweater Dress, Leather Belt, and Ankle Boots

A belted turtleneck dress is all it takes + a healthy dose of confidence. Without a belt, a turtleneck sweater dress may tend towards shapelessness, but cinch one in with a leather belt around the waist and you’ve got a whole different silhouette. We reach for ours in fleece lined tights + ankle boots, adding on a puffer vest if we know we’ll be outside for more than 10 minutes. Great for errands, travel days, + Fridays at the office when you want to look like you’re together (we like ours in airports). Bonus: No more scarf-snagging-on-your-bag-straps business!

7. Flannel Shirt Dress, Fleece Lined Leggings, and Lug Sole Boots

This is the ensemble that would make it through a weekend at the cabin. Like the flannel shirt dress, easy like a dress, but with the cosiness of a button-up shirt. Perfect for mornings when you’re still half asleep! Our trick: Fleece lined leggings (instead of tights) for maximum coziness + flexibility, + lug sole boots for confidently stomping down icy sidewalks. We’re thinking post-pumpkin farm, Christmas tree shopping, + lazy Saturdays. Quilted vest + beanie to finish (firewood chopping optional).

8. Black Long Sleeve Midi Dress, Oversized Blazer, and Loafers

Ever feel like your office is freezing one moment + sauna-warm the next? A black long sleeve midi dress can also hit the formal note, just add an oversized blazer on top for shape without the stuffiness of a suit. This dress + blazer combo means you can still look office-appropriate while being able to shed the blazer when the heater kicks on (just drape it over the back of your chair, darling). Perfect for client lunches, giving presentations, + generally looking like you’re in control of the situation (ahem). Black loafers + a structured tote + a statement ring (because why not use jewelry to make a statement about your feelings on quarterly goals?) to finish.

9. Cable Knit Sweater Dress, Cream Tights, and Shearling Boots

Cream. On cream. (You look like a very expensive snowflake, to be precise.) A cable knit sweater dress adds texture to the look, while cream tights extend the colour palette for a considered, intentional look. We like ours with our shearling lined boots (après ski vibes, even if you’re just walking up the parking garage ramp!), making it great for holiday markets, coffee dates, + winter photoshoots. Camel coat to finish (bring a lint roller, forage for hot chocolate with care).

10. Satin Midi Skirt Dress, Fitted Cardigan, and Kitten Heels

Who says you can’t wear a satin dress in the winter?! We style ours with a buttoned + fitted cardigan, so it looks like we’re wearing a skirt + sweater (warm + polished, if you will). Great for work parties + holiday brunches when the dress code is a little iffy. Pair kitten heels with sheer tights to keep things looking proportionate, and throw on a long wool coat to make getting out of the car less tragic.

11. Puff Sleeve Knit Dress, Patterned Tights, and Mary Janes

Our trick for not looking like a marshmallow when going head-to-monochrome: texture, texture, texture. The puff sleeves give this dress a cute + playful vibe (hello, winter!). We love wearing it with a print (but not too print-y) pair of tights – think houndstooth, ditsy florals, + small-scale polka dots – + Mary Janes for a vintage-y edge. Perfect for birthday brunches, gallery hopping, + generally feeling like you’re starring in a feel-good movie. A short wool coat and small shoulder bag would probably help with the balance.

12. Wool Pinafore Dress, Striped Long Sleeve Tee, and Chelsea Boots

These wool pinafores (grown up overalls, if you will) are warm + cute – the perfect antidote to dreary days! We love ours with a basic striped tee (instant French-girl energy, we promise), + a cross-body bag, making it perfect for casual Fridays + weekend brunch dates. Pro tip: The open sides make it easy to add on a turtleneck on extra chilly days. I’d style it with black tights and Chelsea boots, and maybe a red beanie to break up all of that navy.

13. Ribbed Bodycon Dress, Longline Cardigan, and Sock Boots

This dress makes us automatically stand up straighter – could be the cut, could be the attitude. We throw on a longline cardigan for a relaxed-yet-polished combo (long cardigans create a long, lean silhouette – bonus points!). Perfect for movie dates (especially if your cinema is set to arctic temps), dinner parties, + wine tasting this winter. Sock boots slide right in for a sleek finish, and a crossbody bag keeps your hands free for the popcorn.

14. Corduroy Shirt Dress, Turtleneck, and Western Boots

A shirt dress in rust or olive brings that warmth, and a thin turtleneck underneath adds a cozy layer at the neck and wrists. We love the slightly thrifted vibe of this dress – belt it to define your waist + wear with a shearling jacket + western boots for extra sass. Bonus points if you ditch the pumpkin spice for peppermint-flavored everything (it’s time, friends).

15. Black Knit Maxi Dress, Cropped Puffer, and Sneakers

It’s like wearing a stylish sleeping bag! This dress is perfect for brisk days + last minute outings (since it literally covers all of your legs + keeps you warm – you barely need to wear anything under it!). Pair with cropped jackets, so your outfit isn’t too long top-to-bottom (think a cropped puffer instead of a long coat – you don’t want to be engulfed in fabric!). Clean white sneakers are perfect for city walking, long days of shopping, or travelling to and from the airport. They are stylish yet comfortable. Add a baseball cap + small hoop earrings for an easy-going vibe that still doesn’t scream just-rolled-out-of-bed.

16. Houndstooth Shift Dress, Black Tights, and Pointed Toe Boots

Houndstooth always makes us feel like we’re headed to brunch at a fancy restaurant (even if we’re actually headed to Target). The shift silhouette + classic print make this dress perfect for low-key winter get togethers, holiday parties, + date night. The look could come across as costumey, but the black tights and pointed toe ankle boots keep things modern and clean.

17. Sequin Mini Dress, Oversized Knit Cardigan, and Tall Boots

We know, we know – sequins in 20 degree weather?! Pair it with something more casual, like an oversized chunky cardigan jacket, to keep things warm and take the try hard factor away. Not only is it possible, it’s also cozy (hello, fun friend that brought a casserole to the party!). Pair with knee-high boots (tights are optional for the brave among us), a faux fur coat, + gloves, perfect for holiday parties, NYE, + girls’ night in.

18. Smocked Midi Dress, Chunky Knit Sweater, and Riding Boots

Wear it with a chunky knit sweater on top and the dress is now a flowy skirt that’s ready for the chilly weather! We love a good smocked dress, + this swingy number is perfect for chilly days (the smocked bodice keeps the dress loose-fitting, + the flared hemline allows for extra knit under the dress for coziness). Perfect for farmers markets, family get togethers, + leisurely weekend walks with a hot beverage in hand. Keep toasty with fleece lined tights + riding boots, + consider adding a wide brimmed felt hat (unless it’s windy – then, perhaps not).

19. Hooded Sweater Dress, Leggings, and Snow Boots

Some days just call for a hooded dress (otherwise known as days when you refuse to deal with frozen ears). A hooded sweater dress feels like your coziest sweatshirt dressed up for company. We love the laid-back vibe of this dress – great for running errands, traveling, + even sledding with the kids (it’s still a dress, people!). Leggings make the dress practical, + snow boots make it winter appropriate (without having to worry about salt stains!). Bonus points for wearing with second day hair (since the hood pretty much takes care of that for you), + don’t forget the mittens + puffer coat (this way you’ll be able to stay outside a full 10 minutes longer than everyone else).

20. Tweed Mini Dress, Black Turtleneck, and Loafers with Socks

Tweed always gives us a cozy, library vibe – we love wearing it on mini dresses during winter. Keep the look casual, warm, + youthful by styling with loafers, black tights, + ribbed socks, + layer a turtleneck underneath for a slightly Parisian + scholarly vibe. A camel coat or black trench completes it, along with a structured bag that holds your laptop and at least two lip balms.

21. Slip Dress, Oversized Crewneck Sweater, and Faux Fur Coat

Wear an oversized crewneck over a satin slip dress to let the hem peek out, and it looks deliberate and a little bit cool. We love the mix of luxe knit + shiny fabrics, giving this dress a casual + dressy vibe all at once – great for holiday cocktails, concerts (that you know will run late), + dinner with the ladies. Pair with ankle boots or heeled boots (depending on how much walking you plan on doing), + a luxe faux fur coat so you’re toasty + don’t have to pose for photos while you shiver.

22. Henley Knit Dress, Fleece Tights, and Duck Boots

We can almost imagine the person that this henley knit dress was designed for – probably sips coffee on the front porch, watches the snow fall, + lives in a cabin in the woods. The henley neck gives the dress a relaxed feel (perfect for days at home when you still want to look cute for the delivery person, weekend getaways, + casual errands). Style with duck boots (perfect for slushy sidewalks) + fleece lined tights. And if you’re heading out for a hike (or to the mailbox, which can count as a hike) in the winter, layer on a waxed jacket and chunky scarf for a slightly outdoorsy look that’s very charming.

23. Long Sleeve Floral Midi Dress, Denim Jacket, and Sherpa Coat

We love a floral print during winter – especially one with darker tones (navy, burgundy, etc). It’s such a ray of sunshine + keeps the winter blues at bay (otherwise known as optimism). On colder days add a sherpa coat. For a more casual look try a denim jacket over it. Wear with ankle boots + black tights to keep the look casual, + consider wearing a knit beanie in a complementary color. Perfect for brunch, church, + dreaming about spring (ahem… we mean early spring!).

Worth Adding to the Closet

What shows up in this post more than once.

• Long Sleeve Ruched Midi Dress. A long sleeve midi that layers under a trench or blazer.
• CUSHIONAIRE Leather Penny Loafers. Real leather that breaks in instead of breaking down.
• befen Genuine Leather Tote Bag. Big enough for a laptop, structured enough to look put together.