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 beanies (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
- Nike Cropped Sweatshirt (also available in a longer length, half-zip, and hoodie)
- Nike Sweatpants
- Monogrammed Teddy Tote
- Golden Goose Superstar Glitter Sneakers
Canada Outfits: What I Wore in Toronto
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.)
- Abercrombie Pearl Button Cardigan Sweater
- Old Navy Faux Leather Pants
- Golden Goose Glitter Superstar Sneakers
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.
- Quince Sweater
- Citizens of Humanity Jeans
- Old Navy Socks (sold out, similar here)
- Something Navy Brown Croc Belt (old; similar here, here, here, & here)
- Sam Edelman Loafers
- Vintage Bottega Bag
Similar Vintage Bottega Veneta Bags
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!
- Quince Cardigan Sweater
- Old Navy Faux Leather Pants
- Silver Pumps
- Pearl Beanie (I’ve had this beanie for years, you can see it back on the blog in 2017 here!)
Dave’s Outfit: Faherty Coat, Faherty Quarter-Zip, Paige Jeans, Golden Goose Slide Sneakers
Canada Outfits: What I Wore in Montreal
Night One
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
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!
- Hill House Plaid Nap Dress
- J.Crew Tissue Turtleneck
- Fleece Tights
- Sam Edelman Laguna Waterproof Boots
- Sezane Beanie
- Sezane Scarf
Night Two
Day Three
- Sezane Sweater
- Sezane Denim
- Moncler Coat (old; similar style here)
- J.Crew Cashmere Socks
- Sam Edelman Loafers
- Sezane Beanie
- Vintage Bottega Bag
Night Three
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.
- Striped Turtleneck
- Faux Leather Pants
- Sam Edelman Boots (sold out; similar here, here, & here)
- Gucci Bag
- Amazon Teardrop Earrings
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 (similar here & here)
- Everlane Tee
- Mango Jeans (also available here)
- Brown Leather Belt (bought in Italy, similar here, here, here, & here)
- Sam Edelman Boots (sold out; similar here, here, & here)
- Lele Sadoughi Headband (a few years old; similar here & here)
Canada Outfits: What I Wore in Quebec City
Night One
I wore this to dinner our first night in Quebec City, which, again, was absolutely incredible. More to come!
- Autumn Cashmere Ribbed Crewneck Sweater
- Mango Jeans (also available here)
- Brown Leather Belt (bought in Italy, similar here, here, here, & here)
- Sam Edelman Boots (sold out; similar here, here, & here)
- Vintage Bottega Bag
Day Two
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.
- Hermoza Dress (worn open as a jacket)
- J.Crew Turtleneck
- Ralph Lauren Pleated Skirt (sold out; similar styles here, here, & here)
- Gucci Belt
- J.Crew Tights
- Stuart Weitzman Suede Sock Booties (also available here)
- J.Crew Faux Fur Bag (old; similar here)
This was a casual exploring-around-town outfit. Nothing exciting, but kept me warm and cozy.
- Turtleneck Sweater
- Citizens of Humanity Jeans
- Sam Edelman Waterproof Chelsea Boots
- Pearl Beanie
- Gucci Bag
- Canada Goose Marlow Parka
Night Two: New Year’s Eve
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. 😉
- J.Crew Lace Top
- Old Navy Sequin Skirt
- Gucci Bag
- J.Crew Tights
- Stuart Weitzman Sock Booties (also available here)
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!
- Striped Turtleneck
- Old Navy Sequin Maxi Skirt
- Fleece Tights
- Ruffled Socks
- Sam Edelman Waterproof Boots
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!
Here’s another chaotic packing photo… 🤪 You can see it got progressively worse before it all got packed and put away!
