What I Wore Last Week

What to Wear in Chicago in December

Here are a few outfits that I’ve worn in Chicago recently… A new leopard workout set for yoga, a festive holiday dinner with one of my favorite brands, a sushi date followed by a concert, a German Christmas market, a trip to the DMV, and more!

Chicago fitness blogger wearing a leopard print workout crop top and high waisted leggings set from Outdoor Voices with a black ribbed long duster cardigan.

Tuesday, November 26th: Yoga

Outdoor Voices Leopard Crop Top  |  Outdoor Voices Flex Leggings  |  Bobeau Duster Cardigan

Avec Les Filles Sherpa Biker Jacket Outfit, Mott & Bow Mom Jeans, Marc Jacobs Pillow Bag

Wednesday, November 27th:  DMV

Aves Les Filles Sherpa Biker Jacket  |  Sanctuary Sweater  |  Mott & Bow Jeans  |  Steve Madden Lucite Heel Booties (old; similar here & here)  |  Marc Jacobs Pillow Bag

Ulla Johnson Multicolored Puff Sleeve Pullover Sweater, Cropped Raw Hem Ankle Jeans, Robert Clergerie Pink Velvet Booties

Thursday, November 28th: Thanksgiving

Ulla Johnson Sweater  |  Old Navy Power Straight Jeans  |  Robert Clergerie Pink Velvet Booties  |  Pink Sunglasses

Chicago fashion blogger wearing leopard sherpa coat with a bodysuit and One Teaspoon jeans with Marc Fisher booties to a concert at Aragon Ballroom.

Friday, November 29th: Dinner at Ora Sushi, Louis the Child Concert

Jonathan Simkhai Leopard Sherpa Jacket (similar here, here, & here)  |  Privacy Please Bodysuit  |  One Teaspoon Jeans (similar here)  |  Marc Fisher Booties  |  Kendra Scott Rings  |  LV Neverfull Pouch

Sezane Blue Gingham Check Sweater, Marc Fisher Booties

Saturday, November 30th: Therapy Appt + Errands

Sezane Gingham Sweater  |  Frame Jeans  |  Marc Fisher Booties  |  Yves Salomon Beanie (old; identical here)

Bows & Sequins at Christkindlemarket in Chicago wearing a pink J.Crew Cocoon Coat and an Ulla Johnson Sweater.

Monday, December 2nd:  Christkindlmarket at the Daley Plaza

Ulla Johnson Sweater  |  J.Crew Cocoon Coat  |  Rag & Bone Jeans  |  Marc Fisher Booties  |  Gucci Soho Disco Bag  |  Pink Pom Pom Beanie

Kelly Chrischilles and Jessica Sturdy at Christkindlmarket Chicago wearing cute winter coats.

Jonathan Simkhai Leopard Sherpa Coat, Yves Salomon Beanie, Steve Madden Croc Booties
Tuesday, December 3rd:  Kiehl’s x Feeding America Event for Giving Tuesday, Dinner at Blue Door Farm Stand

Jonathan Simkhai Leopard Sherpa Jacket (similar here, here, & here)  |   Sezane Sweater  |  Old Navy Power Straight Jeans  |  Steve Madden Booties (on sale!)  |  Pom-Pom Beanie  |  LV Neverfull  |  J.Crew Trouser Socks

Sezane Brown Sweater Outfit

Calia by Carrie Underwood Blue Leopard Print Leggings

Wednesday, December 4th: Chi50 Class

Calia Long Sleeve Tee  |  Calia Blue Leopard Leggings  |  adidas Ultra Boosts  |  Pilates Socks  |  Aviators  |  Chenille Scrunchies

Preppy Chicago blogger Bows & Sequins at Hampton Social wearing Vineyard Vines with white velvet jeans and a plaid tartan wrap scarf and holiday headband.

Thursday, December 5th:  Holiday Dinner with Vineyard Vines at Hampton Social

Vineyard Vines Navy Sweater  |  Vineyard Vines White Velvet Jeans  |  J.Crew Plaid Pumps (old; similar here, here, & here)  |  Kate Spade Navy Bag  |  Tartan Wrap  |  Green Velvet Jeweled Headband  |  Kendra Scott Earrings  |   Kendra Scott Rings

Vineyard Vines white velvet jeans, plaid tartan wrap scarf, J.Crew blackwatch plaid pumps, Kate Spade navy blue bag, green velvet jeweled headband

orange duster cardigan, golden goose leopard glitter sneakers

Friday, December 6th:  Dinner at a Friend’s House

Old Navy Ribbed Long-Sleeve Tee  |  Vineyard Vines Jeans  |  Sanctuary Cardigan (50% off!)  |  Golden Goose Sneakers

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  1. 12.19.19
    Rena said:

    So cute the looks you wore!
    xx from Bavaria/Germany, Rena

    • 12.19.19
      Jessica said:

      Thank you!

  2. 12.19.19
    Cynthia said:

    I just love your style! You switch it up so seamlessly- preppy, kinda punk influence, then sweet and girly.

    • 12.19.19
      Jessica said:

      That’s so nice of you to say, and definitely a compliment that means a lot to me! It used to kind of bother me that my style felt all over the place (and tbh, still kind of does when I necessarily ‘put myself in a box’ when a brand or blog partner asks me to describe my style), but I just dress to my mood and wear what I like! ‍♀️ While I definitely think I gravitate more towards classic pieces as I’ve gotten older, I still find it fun to experiment. 🙂