Winter going-out season in Canada is a special kind of struggle. You want to look hot, but it’s literally minus twenty. You’re torn between dressing for the ‘fit or dressing for survival. And, of course, there’s the eternal dilemma: bring a coat and deal with coat check chaos, or risk frostbite for the sake of the outfit?

If you’ve ever stood outside waiting for an Uber in sheer tights, regretting all your life choices, this guide is for you. Because yes, you can look cute and still feel your fingers by the end of the night. Here’s how:

1. The Coat Dilemma: To Bring or Not to Bring?

We’ve all been there—debating whether to bring a coat because where will I put it? But let’s be real, shivering in a mini dress while waiting for your Uber isn’t the look.

• If the venue has coat check: use it. Yes, it’s annoying, but you’ll thank yourself later.
• If there’s no coat check: bring a cropped puffer or oversized blazer—something you won’t mind draping over a chair or holding for half the night.
• If you refuse to bring a coat: at least wear a warm scarf. It makes a surprising difference, and you can drape it over your shoulders inside.

2. Pick Your Shoes Wisely

Winter sidewalks are unpredictable—one minute, you’re strutting confidently, the next, you’re Bambi on ice.

• Heeled boots > Stilettos – Block-heel boots or platform booties keep the outfit cute and give you actual stability.
• Tights + loafers or chunky boots – If your night involves lots of walking (or questionable sidewalk conditions), this combo is stylish and practical.
• Waterproof spray is your best friend – Protects your shoes and your dignity when you step in a slush puddle.

3. Strategic Outfit Choices = Maximum Warmth

If you’re not trying to wear layers under your outfit, choose pieces that naturally keep you warm:

• Long-sleeve mini dresses – You still get the legs-out moment, but without freezing your upper half.
• Leather pants + a fun top – Warmer than jeans, looks effortlessly cool, and pairs with literally anything.
• Sweater dresses – Cozy, chic, and works with knee-high boots for extra warmth.

4. Accessories That Actually Help

• Faux fur or shearling bags – They double as a hand warmer when you’re outside.
• Statement gloves – Opera gloves, leather gloves, or even knit ones in a fun color—warm and stylish.
• Earmuffs or a chic beanie – Trust me, keeping your ears warm makes a huge difference in how long you last outside.

5. Plan the Exit Strategy

There’s nothing worse than wrapping up the night, only to realize you have to trek through a blizzard to get home. Be prepared:

• Pre-book your Uber or cab – No one wants to be the girl standing in the cold refreshing the app.
• Pack an emergency pair of socks – If you’re wearing heels, this is a lifesaver for post-bar walks home.
• Go out with a friend who also values warmth – Because we all have that one friend who insists she’s “not cold” in a tiny dress while you’re questioning your life choices.

Yes, winter going-out outfits require a little more effort—but with the right tricks, you can still serve looks without turning into an icicle. Just remember: no outfit is worth freezing to death over (well… almost no outfit). Dress smart, layer up, and embrace the cold—because nothing says Canadian winter like surviving a night out in style.

Love, Laura