Yesterday I shared my Chicago Holiday Bucket List, and today I’m back with outfit ideas for each activity – this was such a fun one to put together! I’m sure you’ve got a few similar events on your calendar, and if you need outfit inspiration, I’ve got you covered. Each look features pieces I actually own, and when something is no longer available, I’ve linked a similar option. I can’t wait to start checking these festive activities off my list this holiday season!
What To Wear: Holiday Bucket List
Ice Skating
It’s probably going to be cold (if there’s ice, that’s a pretty good clue!), so for this activity I’m planning to wear a fair isle sweater with cropped denim and black boots. The fair isle adds a festive touch, and the cropped denim helps keep you from tripping over your pants. I’ll also layer a base layer underneath (not pictured) and top it off with a cropped puffer jacket for extra warmth and easy movement.
Festive Dinner
A cozy and festive dinner definitely calls for a red sweater, don’t ya think? To dress it up, I’m planning to add heeled ankle boots, a long wool coat, a suede shoulder bag, and chunky knot earrings. If you want to make the look even more dressy, you can swap the jeans for satin or velvet pants.
A Christmas Carol Play
I love getting dressed up to see a show. Honestly, I’d do it every week if theater tickets weren’t so pricey! For this look, I’m wearing my new mesh blouse and knit skirt (both from Mango) paired with my knee-high boots from Sézane. For outerwear, a long wool coat feels like the chicest option, and for accessories, I added a little black bag (mine is vintage, but this one is similar) along with some chunky gold earrings.
Drive Thru Christmas Lights
Driving around to see Christmas lights with a cup of hot chocolate is honestly one of the best parts of the holidays. For this look, I went full comfort with sweatpants and clogs, but added a chic, modern touch with a cozy cable knit sweater and festive red socks.
Christmas Market
When we visit the Christkindlmarket in downtown Chicago, I want to look polished yet a little outdoorsy, and I think a flannel paired with a cable knit sweater works perfectly. You can wear the plaid shirt under the sweater or drape it like a scarf – both options look great. I paired this with indigo jeans (just ordered these!), brown boots (or swap for flat Chelsea boots if that’s more your style), and added gloves and a beanie to stay warm.
Home Alone Tour
This one’s a bit niche for Chicago, but if you have any outdoor holiday events where you want to be comfortable and casual (yet still photo-ready), this is the look. A red sweater (I’m finding so many ways to style this!) paired with polished indigo jeans, suede loafers that feel like slippers, a cozy wool coat, and fun red socks makes for the perfect festive outfit.
Walkthrough Lights Display
When we visit the Zoolights at Lincoln Park Zoo, it will be dark and probably pretty cold (though in the Midwest, you never really know!) I’ll be layering up with this look plus a base layer on top and bottom. These boots are super comfortable for how stylish they look – they even have arch support! The outfit is warm but still feels modern and put-together.
Holiday Train Ride
For our holiday train ride, I’ll be wearing something like this: a denim shirt (with a base layer underneath!), relaxed-fit jeans, a cozy wool coat, and red flats with socks. If it’s extra chilly, you could also add a scarf or drape a sweater over your shoulders for warmth.
Read More:
Thanksgiving Outfits 2025
Fall Accessories For 2025
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