What to wear to work this winter: 10 tips for standing out when it’s cold

what to wear to work this winter

With the temperature dropping as we speak, it seems all we want to wear these days is a pair of long johns and layers of blankets. But since many of our day-to-day activities involve being present in an office, rather than lounging our couch, finding that balance of cozy and professional is not easy at all. And when you add wanting to stand out in an office full of suits into the equation, we can see why dressing for work isn’t anyone’s fave morning activity. To help simplify things, our Style Panel stepped up to the challenge. From sharing key winter pieces to smart styling tips, here are 10 chic looks to help inspire your next work outfit.

Question 148: How do you dress for work during the colder months? Read the answers now! »

Jump to: AMANDA MONTGOMERY | AMANDA REID | BECKY KUNG | CONNI JESPERSEN | CRISSY FUNDARO | KAYLA SHORT | LAURA MITBRODT | LEE VOSBURGH | STEPHANIE KOCH | TERESA YOO


what to wear to work this winter

Amanda Reid, 27
Windsor| Rose City Style Guide

As the weather dips, it is always challenging to dress for the office since all anyone would rather do is snuggle up. That’s why I embrace everything cozy with a slouchy and warm sweater. By pairing an oversized knit with structured and polished pieces, I am able to balance the causal and professional for an overall stylish look.

Amanda’s wearing: Sweater, Aritzia. Watch, c/o Daniel Wellington. Skirt, Joe Fresh. Heels, Topshop. Laptop bag, Kate Spade. Sunglasses, Ray Ban.


what to wear to work this winter

Teresa Yoo, 25
Toronto | What T Loves

I feel fortunate to work in an environment where I can be fashion-forward and unique in style. However, it is still a challenge to carry warmth and style at the same time during colder months even though there isn’t much restriction at my workplace. In that case, it’s time to bring on the layering game! My ride-or-die tip in layering is to go for thin layers with different textures to build up the whole outfit. This way, the clothes won’t be so bulky and coats or jackets will actually fit you without giving you that uncomfortable tightness. At the same time, the variation in texture will still keep you fashionably on point.

Teresa’s wearing: Coat, vintage. Pleather vest, Zara. Denim shirt, H&M. Turtleneck, Zara. Pants, Mango.


what to wear to work this winter

Conni Jespersen, 35
Toronto | Art in the Find

Coming from the warmer San Diego temperatures to the colder climate of Toronto has me preparing for work in a completely different way! I’ll pull together the same staple pieces (ie. a button down silk top and pencil skirt) and layer in a new, warmer way. How do I do that? Great looking opaque tights (in both prints and solids) and faux fur layers, like this vest. Layering under and over has saved my life in terms of style and warmth.

Conni’s wearing: Skirt, Banana Republic. Booties, Dolce Vita. Faux fur vest, Zappos. Tights, Nordstrom. Bag, Rebecca Minkoff. Top, Diane Von Furstenberg.


what to wear to work this winter

Becky Kung, 32
Calgary | Velvet & Vino

My universal tip is to pay special attention to your overcoat when dressing for the cooler weather for work. Overcoats have become the stylish statement piece for outfits. Not only the perfect layering piece to fight off the cool weather, overcoats can also be worn as a part of the outfit for indoors. This makes it so important to invest in a wool overcoat that’s warm, yet light enough to move between outdoors and indoors. I like to finish my look by layering the wool overcoat over my neck-tie blouse and a tweed skirt.

Becky’s wearing: Overcoat, blouse and skirt, Topshop. Boots, Sam Edelman. Clutch, Rudsak


what to wear to work this winter

Kayla Short, 29
Halifax | Short Presents

Dressing for the office doesn’t need to be stiff and structured all the time. Turtlenecks and skirts can actually be pretty comfortable while also very sophisticated if you let them. Depending on your job or office setting this can vary of course, but I love the idea of pairing a turtleneck over a shirt dress, as seen above. I love the little peek-a-boo of the collar at the top, and the flow of the skirt beneath. It’s pretty simple, but I think that’s what I love about it. You can also consider what you choose to do with your hair. I kind of like this laid back ponytail version of a French braid it’s effortless, but looks super put-together still.

Kayla’s wearing: Dress, Jealous Tomato via Envy Clothing. Turtleneck, Vera Modo via Envy Clothing. Shoes, Nine West. Bag, Sneha Varma. Watch, Bulova. Sunglasses, Céline via Smart Buy Glasses.


what to wear to work this winter

Laura Mitbrodt, 31
Victoria | Laura Jane Atelier

Since I live in Victoria I don’t have to deal with extreme cold and snow like the rest of Canada. In the colder months I like to layer my look with a classic wool coat and a warm sweater. This coat is perfect when I have to meet clients because it is chic and easy to throw on when I am running out the door. I find that a statement hat like this black beret completes the look and keeps my head warm.

Laura’s wearing: Coat, SheIn. Sweater, H&M. Pants, Club Monaco. Shoes, vintage. Socks, Target.


what to wear to work this winter

Lee Vosburgh, 28
Guelph | Style Bee

I’m very fortunate to have the opportunity to work from home so technically I could wear sweatpants and hoodies all day if I really wanted to. But the truth is I don’t. I actually find that getting ready and looking presentable really helps me get into a working mindset. I usually leave the house at least a few times a day whether it’s to walk my dog, run errands, grab a coffee, pick up supplies for a shoot or meet with a client. So I go for looks that are simple, comfortable and chic. Lately with the weather getting chilly I’ve been turning to wool layers, boots and cozy scarves.

Lee’s wearing: Scarf, Block Shop Textiles. T-shirt, Everlane. Sweater Cape, First Rite. Denim, Yoga Jeans. Boots, Rachel Comey. Bag, Primecut.


what to wear to work this winter

Amanda Montgomery, 29
Toronto | Latest Wrinkle

As a freelancer who works from home, I sometimes tend to stay in my cozy pajamas as I work through the winter months. But when I head out for meetings or bounce between events, layering is key! Black tights are my best friend in winter, as I have a hard time giving up my skirts and dresses. One of my favorite layering pieces is this cape, because it is so easy to toss on and stay warm!


what to wear to work this winter

Crissy Fundaro, 36
Montreal | Some Velvet Morning

Layering is always a big trend during the colder months. It’s a practical way to dress and probably most seen. I mostly work from home, but when I am in the office, I’m fortunate that it’s business casual wear and jeans are allowed 5 days a week. You can find me wearing jeans with a light shirt and cute cardigan/sweater.

Crissy’s wearing: Jeans, H&M. Shirt, J.Crew. Cardigan, Chicwish. Bag, Gigi New York. Shoes, Coach.


what to wear to work this winter

Stephanie Koch, 30
Kelowna | Inherited Jeans

November is an odd time of year to find something to wear. It could snow or it could be 10 degrees by 2pm. How you commute to work will probably change your strategy in regards to how to be prepared for weather but also look appropriate when you arrive. Right now I am driving to work, but when I lived in other cities and was taking public transit, I would go to work in boots or water proof footwear and keep a pair of heels or dressier shoe at my desk for when I arrived. Wearing a hat that protects your hair instead of flattening it, and topping off with a long coat protects the clothes you work in all day. I have been wearing a lot of knits that have room for a lighter layer underneath, paired with a more tailored pant to balance the bulk and casual nature of a knit.

Stephanie’s wearing: Hat, Urban Outfitters. Coat, Pink Martini via Winners. Sweater, H&M. Pants, Club Monaco. Shoes, Topshop. Bag, Marc by Marc Jacobs.