I love all the holiday outfit round-ups that all of us content creators do, however, I often find that I cannot relate to them nor find them useful because if I went out in most of them I would be the town crazy lady. A lot of them are also not winter boot friendly, which is a requirement in Canada since we often wear our winter boots from our house to the host’s house and then don’t wear any shoes inside their house. So I am going to put together some outfits for those of us who live in small towns and can’t run around in head to toe glitter and feathers (even if we may want to). I don’t completely cater to my small town, if I did I’d never wear anything but jeans and sweats, but I don’t like to completely stick out like a sore thumb.

I also don’t like to buy clothes that have a limited number of occasions, especially if I am investing in them, I prefer pieces that can be worn a ton of different ways, with an accessory or a single piece that elevate the other items for the occasion.

This one is for the really cold days where you need to be outside. Maybe walking through neighborhoods looking at light displays or a Santa Claus Parade. This would probably be my most worn look of this whole post (and the parka is the one I wear all winter).

Bucket Hat // Earrings // Scarf // Sweater // Jeans // Boots // Parka

This would probably be my second most worn outfit of this, it would be perfect for casual nights out (the dress is too short of work, or I would totally wear it to work).

Dress // Tights (this picture is Wolford, but realistically I’m buying Snag tights for the winter) // Headband (I have a very similar one from Anthropologie a few years ago) // Tall Boots (these would keep your legs slightly warmer, and come in three calf sizes) // Doc Martens

This is what I would wear in the Hallmark Movie of me going home for the holidays. We might need to swap the suede coat for a wool coat because I don’t know how warm it would be but I just love the look of it so much.

Toque/Beanie // Mittens // Hoops // Sweater // Jeans // Trench // Boots (notice the product repeating, I meant it when I said that I buy items I can repeat).

If I’m honest, I spend the vast majority of my holidays on my parents’ couch and I wouldn’t have it any other way. So super comfy and stretchy is the way for me.

Earrings // Undershirt // Sweater // Yoga Pants // Socks (I know Ugg socks sounds ludicrous and so bougie, but they are incredible) // Slippers

If I was the type to get dressed up to decorate my tree and not do it in ratty sweat pants, I like to imagine this is what I would wear. This could be perfect for a daytime work or other holiday party, dinner at a friend’s house, or if you have a partner to go over to their parents’. Similar to the outfit with Doc Martens, the tall boots will keep your legs warmer. This would also be what I would wear on Christmas Day sans shoes (maybe slippers).

Earrings // Sweater // Skirt // Tights // Pumps // Boots

To me this would be a perfect Christmas Eve outfit, especially if you’re family goes to church, it is covered up, warm, but still beautiful (and it is comfortable if you eat a big dinner on Christmas Eve, or just a lot of cookies).

Earrings // Dress // Tights // Boots

This is another Hallmark movie outfit, this is so chic. When I imagined what I would be wearing as an adult when I was a kid, this was it.

Earrings // Dress // Coat // Boots

To me this screams, fun and put together at the staff Christmas party. Boots if there’s snow on the ground and fun red pumps if you don’t have far to walk or you live somewhere without snow.

Headband // Earrings // Sweater // Pants // Pumps // Boots

This is elevated and weird for most small towns, but there is something about pants that make people feel like you aren’t *too* dressed up, even though putting on a dress is the easiest outfit.

Earrings // Sweater // Pants // Heels (I wore these to my sister’s wedding and they are super fun, kind of uncomfortable, but super fun) // Boots