I don’t know about you, but I’ve already started thinking about what I’m going to wear for all the holiday activities on my calendar this season. If you need some inspiration this year, here are my holiday looks for 2026. These ideas cover the range of holiday occasions you may have from a kid's class party to a fancy night out at The Nutcracker ballet and everything in between.
Note that I own a lot of the items I’m sharing in this post. I like to be able to vouch for the items I link most of the time. There are also a few fun holiday finds on here that are currently on my wishlist. Happy holidays!
Holiday Looks For 2026
I saw this top recently and couldn’t get it out of my head for several days - so I bought it, ha! It’s not my usual aesthetic but the jewel tones and olive-y color sold me. For Thanksgiving, I’d pair it with these polished (but stretchy!) black pants, and some suede slingback heels.
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Taffeta Top / Kick Flare Pants / Burgundy Coat / Suede Slingback Heels / Polish / Earrings / Suede Bag
This layered look feels a bit outdoorsy but in a chic way (just how I like it). I actually own everything here and plan to wear this exact outfit when we go get our Christmas tree. Granted, we’ll probably be buying it from the lot down the street and not from a tree farm, but I’ll still look cute! This outfit features a new fair isle cardigan I just bought from Alex Mill - it’s excellent quality. I layered a thin turtleneck underneath and a waxed jacket on top for warmth. On bottom are my new favorite jeans from AYR and practical (and durable!) Chelsea boots from La Canadienne.
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Turtleneck / Fair Isle Sweater / Jeans / Waxed Jacket / Cashmere Socks / Boots / Beanie
There is nothing more Christmasy than strolling an outdoor Christmas market with a hot mug in your gloved hands and the twinkling lights all around you. For this occasion, I would wear a warm cable knit sweater, a long wool coat (this one is on my to-buy list for winter!), a pair of indigo barrel jeans, and my favorite brown ankle boots. The woven suede tote bag adds richness and texture, too.
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Cable Knit Sweater / Long Wool Coat / Indigo Barrel Jeans / Brown Ankle Boots / Woven Suede Bag / Polish
For a holiday date night, perhaps at a pop up bar maybe, I’d wear one of my go-to date night combinations - a blazer and full length jeans. This would work with a plain black blazer, but I’m loving this velvet one in this chartreuse color. For under the blazer, I chose a white tuxedo shirt with a black necktie. I LOVE this look.
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Necktie Top / Chartreuse Blazer / Black Jeans / Slingback Heels / Black Shoulder Bag / Earrings
This work party look is one of my favorites on this list, but also a little unexpected, too. I’ve been loving all the fringe I’ve been seeing lately, and it works well for the holidays. I could totally see myself wearing this top with some light wash jeans and heeled sandals for a date night outside of the holidays. For this outfit, I paired the fringe top with black silk pants (these come in multiple inseam options!) for a head-to-toe flowy look. And every party look needs some accessories - I added some drop earrings and a beaded bag (I own and love this one from Staud).
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Fringe Top / Silk Pants / Silver Heels / Beaded Bag / Drop Earrings / Lipstick / Polish
I love the idea of getting a little festive to attend my kids’ classroom holiday parties. And bonus, this is really comfortable, too. I own all of of these things (except for the glasses and travel mug!) and can vouch for each piece.
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Plaid Flannel / Red Fleece / Barrel Jeans / Sneakers / Glasses / Travel Mug
Here’s what I would wear for an afternoon holiday tea which is on my holiday bucket list this year. It’s so much fun to get a little dressed up for these holiday events. I found this cute fair isle sweater dress which you can definitely wear beyond the holidays. I think it pairs well with some black knee high boots and a long wool coat.
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Sweater Dress / Coat (similar) / Boots / Earrings / Bag
This monochromatic look is so elegant and chic. I also really love the texture combination of a knit paired with a silk skirt. I would do my hair up in a low chignon if I were wearing this to the ballet.
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Burgundy Sweater (similar) / Burgundy Silk Skirt (similar) / Slingback Heels / Shoulder Bag / Drop Earrings / Lipstick / Polish
One of my favorite things about the season is all the twinkly lights everywhere. We always try to make it to an outdoor lighting, usually it’s the Zoolights at Lincoln Park Zoo, a Chicago holiday tradition. For this occasion, I put together this look with a cute fair isle sweater, an ankle length wool coat, indigo jeans, and some flat boots. I added a beanie and gloves for extra warmth.
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Fair Isle Sweater / Wool Coat (size down) / Indigo Barrel Jeans / Brown Boots / Beanie / Gloves
And lastly, to wrap up the season, here’s what I plan to wear on Christmas morning while we are opening gifts. A little cozy and a little festive.
Navy Sweatshirt / Plaid Pajama Pants / Cozy Socks / Faux Fur Blanket / Glasses / Mug
Read More:
Holiday Books To Add To Your Reading List
My Chicago Holiday Bucket List
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