What I Wore in Canada

Canada Outfits: What I Wore Last Week in Toronto, Montreal, and Quebec City

Here’s a look at all of my Canada outfits! While I was packing, I knew it was important to dress for the weather, but I wanted to have a little fun with fashion and wear some cute outfits, too.

I will say, the winter weather was definitely a bit more mild than it usually is in Canada this time of year. Instead of snow, we got a lot of rain when we were in both Toronto and Montreal. There was finally some snow on the ground when we got to Quebec City, though!

For my outerwear that you’re not seeing in the majority of these photos, I brought two coats (my big Canada Goose parka and my lighter Moncler puffer jacket), which was definitely the right move with the amount of precipitation we had. I only packed one scarf, but at least three beaniesย (grey, white, black) and two pairs of gloves (black and brown). I wore all three hats multiple times, as it was nice to switch it up.

If you want to read more about our Canadian road trip, click here to jump over to that blog post.

What I Wore for Long Car Rides

Brown Nike Phoenix Sweatshirt and Jogger Sweatpants, Poolside Slopeside Monogrammed Teddy Tote

Canada Outfits: What I Wore in Toronto

Abercrombie Pearl Button Cardigan, Old Navy Faux Leather Loose OG Pants, Golden Goose Glitter Superstar Sneakers

Since we drove to Toronto on Christmas Day, we knew a casual meal in Chinatown was probably going to be our only option for dinner. I didn’t get a picture of my outfit at our hotel, so this one is from my packing notes on my phone. (I always try on every single outfit and take a picture to make getting dressed on a trip a breeze! Don’t mind the rolling rack and packing frenzy happening behind me.)

Quince Cashmere Cardigan, Citizens of Humanity Charlotte Jeans, Sam Edelman Laurs Loafer

I wore this for a full day of sightseeing and wandering around Toronto. I think this might be the first time you’re seeing this vintage Bottega bag that Dave’s mom passed down to me over Thanksgiving! It’s the most buttery soft brown leather and I’m absolutely obsessed. I need to ask her what year she got it, as I haven’t seen a similar style in quite some time — especially with the gold hardware! (This style on The RealReal is the most similar I’ve found!) I believe it’s supposed to be more of a shoulder bag, but since I have a short torso, it works as a shorter crossbody on me.

Similar Vintage Bottega Veneta Bags

Travel couple dressed for dinner in Toronto, Canada.

This is what we wore out for dinner on our second night in Toronto! Kept my same sweater on, but swapped my pants and shoes since we Ubered to the restaurant. If you’re interested in reading more about what we did in Toronto and our incredible meal, read this post!

Dave’s Outfit: Faherty Coat, Faherty Quarter-Zip, Paige Jeans, Golden Goose Slide Sneakers

Canada Outfits: What I Wore in Montreal

Night One

J.Crew Black and White Lace Top with Gold Buttons, Mango Tweed Skirt, Sheer Tights Fleece Leggings, Mach & Mach Dupes

These fleece leggings that look like sheer tights were purchased specifically for our trip! I ended up wearing way more outfits with pants or jeans, but they were nice for keeping me warm with the dress and three skirts I packed. I love the look of them, but I will say, these in particular have a weird fit in the butt. (Two seams that almost made me feel like I was wearing a diaper??) You can see it in the ‘hip design’ photo on the website… The “U design to lift the buttocks.” 💀 I need to research and find a pair I can confidently recommend.

Day Two

Canada Outfits: Plaid Nap Dress Layered for the Winter

LOL – I can’t believe I’m even posting this picture, but it was the best I got that day. A little IG vs Reality moment… I imagined wearing this outfit and getting a super cute picture at the Christmas market, but it was a cluster. I didn’t take a mirror pic because we snapped this on the way home, not realizing it was a complete flop. That’s what I get for not double-checking the camera settings!

Plaid Dress Layered for the Winter

Night Two

Abercrombie Pearl Button Cardigan Sweater, Old Navy Wide Leg Jeans, Silver Pumps, Silver Mini Bag

Day Three

Sezane Red Sweater, Sezane Brut Sexy Jeans, J.Crew Cashmere Socks with Sam Edelman Laurs Chunky Lugsole Loafer, and vintage Bottega bag.
Travel blogger standing in front of the Ritz Carlton in Montreal with a giant red bow decoration for Christmastime. She's wearing a Moncler coat, jeans, and brown loafers.

Night Three

Travel blogger dinner outfit in Montreal, Canada: Amazon's Toteme Sweater Dupe Black and White Striped Turtleneck,  Faux Leather Pants, Gucci Marmont Bag, and cream colored boots by Sam Edelman

This was one outfit that was a total wildcard, as I did not plan for it. I didn’t feel like wearing the pleated skirt I packed, as most of our reservations (at really great places!) were on the more casual side. That’s probably more of a conversation for the style nowadays, but I wanted something warm and cozy to wear for dinner. I ended up pairing this swingy turtleneck (that I LOVE) with my faux leather pants and cream-colored boots. Not pictured here, but I ended up putting on these chunky gold earrings and it totally balanced everything out.

Ivory Boots

I want to quickly chat about these cream-colored boots, as I wore them a lot on this trip! Sadly, they’re from last season and nowhere to be found. My pair is the Sam Edelman ‘Taryn‘ Boot in Ivory. However, the brand launched a very similar ‘Moe‘ boot this year, but it has a higher heel. If you want them, I found the best price (only $70) here!

A few similar styles by other brands I’ve found… Vince Camuto Quindele Bootie, Schutz Blake Bootie, Staud Wally Ankle Boots, Vince Ravenna (on sale!), M.Gemi Veronica, Lifestride Sienna at DSW, and Marc Fisher Jarli.

Day Four

Ralph Lauren Sweater, Mango Wide Leg Jeans, Cream Colored Booties

Canada Outfits: What I Wore in Quebec City

Night One

Autumn Cashmere Ribbed Sweater, Mango Wide Leg Jeans, Sam Edelman Cream Booties, Brown Bottega Shoulder Bag, Brown Leather Belt

I wore this to dinner our first night in Quebec City, which, again, was absolutely incredible. More to come!

Day Two

Hermoza tuxedo dress worn as a coat for a fancy hotel brunch. Black turtleneck, cream pleated skirt, sock booties, Gucci belt, and faux fur bag.

On New Year’s Eve Morning, we did the fancy brunch at our hotel so I wanted to dress up a bit more for that! I took my floral tuxedo dress (last seen here in this post) and wore it open like a jacket over a turtleneck and skirt. Originally, I had packed a black lace turtleneck to wear with this outfit, when I was planning on wearing it to dinner. Since that felt like too much for daytime at a family-friendly hotel, I swapped it for a J.Crew tissue thin turtleneck.

Pearl Beanie, Amazon Sweater Toteme Turtleneck Lookalike, Sam Edelman Laguna Boots

This was a casual exploring-around-town outfit. Nothing exciting, but kept me warm and cozy.

Night Two: New Year’s Eve

J.Crew Black and White Lace Top with Gold Buttons, Black Sequin Maxi Skirt, Stuart Weitzman Sock Booties, Gucci Bag

I was most excited about this outfit to wear on New Year’s Eve, but we ended up changing our plans a bit. I threw it on just to take a pic, but forgot to tuck in my shirt, so if you’re using this as inspo for any dressier winter outfits, just tuck in your shirt to balance out the maxi. 😉

Amazon Sweater Dupe for the swingy Toteme Turtleneck, worn with a sequin maxi skirt, fleece tights, ruffled socks, and waterproof lugsole boots for Toboggan, an outdoor music festival on New Year's Eve in Quebec City

This was another audible outfit I threw together at the last minute. I wanted to wear sequins and be festive since it was NYE, but the town of Quebec City hosts a (free!) full-blown music festival to ring in the New Year. It was so much fun, but I knew I needed something warmer and waterproof shoes. Since this was the only turtleneck sweater I packed, I paired it with the sequin maxi skirt and lugsole boots and kind of loved how it turned out. Felt very French!

What I Wore in Vermont

It was really a mix and match of previous pieces for dinners out in Vermont, so I didn’t manage to take any photos. I pretty much wore a version of this outfit each night: these Sesame-colored waterproof boots, these stretchy jeans, and this cozy sweater!

Quince Cashmere Sweater: Jenni Kayne Dupe

Here’s another chaotic packing photo… 🤪 You can see it got progressively worse before it all got packed and put away!

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