Chicago Outfit Roundup + Looks Under $100! (Winter Fashion Outfits)

winter fashion outfits

Am back home and already missing the city! It is so hard to get motivated to look and feel cute throughout the winter so I tried my best with these winter fashion outfits.

It was such a nice week of exploring (often aimlessly) while freezing my fingers, toes, and entire face off. I had told myself I would walk everywhere, which I did all but 2 times. Was fortunately sunny and picture perfect the entire trip but below zero with wind chill! Had spotted “Watch Out For Falling Ice” signs all over town and the only thing going through my mind was, “Yeah, that’ll be me if I lose my balance.” Loved every second though!

Sharing my outfits from this week and some tourist bits because this was basically my holiday! Plus, I just get so excited when putting together what to wear each morning. Looking through the combinations I decided to go with this past week, each was different even though I used a few of the same pieces. Below each day I have recreated the looks and the pieces are all under $100.

Links below each!

winter fashion outfits

When I first arrived and so darn excited and happy to be there. My day started off with spilling coffee all over these jeans, but it didn’t even matter!

winter fashion outfits

Knit hat / Bell sleeve sweater / Gloves / Jeans / Sneakers / Bag


 

winter fashion outfits

Had a meeting this day so I went simple.

This sweater is one of my favorites, I love super long sleeves. Couldn’t find this sweater online but the light grey one below seems super comfy too. Later changed into my sneakers for when I was out walking around Millennium Park and around the city!

winter fashion outfits

Sweater (similar, also similar) / Earring barBlack skinny pant / Necklace / Black booties


 

winter fashion outfits

Casual walk day in West Loop! These photos are from the enchanting Soho House. Was so enamored by the beauty I just kept staring at how stunning the place was, plus decorated for the holidays.

Ventured to 2 other parts of the city and refused to take a ride anywhere! The sweater I wore is from Anthropologie and the only thing that could make it better would be billowy sleeves like the one below!

winter fashion outfitsCrop turtleneck/ White skinny pant / Sneakers / Backpack / Sunglasses


 

winter fashion outfits

Determined to visit Navy Pier this morning. Was the only soul there! It was beautiful out and actually really peaceful. Loved it.

I also really love layering a basic t-shirt dress under any sweater. It’s a super comfy and feminine look. These were wool tights so were fortunately thicker than normal ones. Wore a long black puffy coat with this!

winter fashion outfits

Sweater (similar, also similar) / HeadwrapScarf / Basic t-shirt dress / Black tight / Black leather booties / Black crossbody

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