Our content has been independently selected and contains affiliate links. If you make a purchase using the links, we may receive a commission.
If there's anyone who understands the beauty of a transitional piece, it's Anna Wisniewski, cofounder of the women's fashion brand One/Third.
One/Third, which Anna founded with fellow fashion industry veteran Coabi Kastan, is all about "perfecting the art of the jacket." Based in Chicago, Illinois, Anna and the rest of the team are well-versed in all the layers — and they share our point of view that a wardrobe should be timeless.
So when it came time to answer the question, "What should I pack for a trip to Chicago in the fall?" we turned to Anna, who revealed her five must-pack items for a visit to the Windy City.
Chicago Style Q&A with Anna Wisniewski
My personal style is…
Classic, sightly dressed up but not stuffy, and layered — I do live in the midwest, after all.
Don’t visit Chicago in the fall without…
A few different jackets — denim. You never know what the weather will be like, but a light jacket and denim can be worn virtually everywhere.
My tried-and-true outfit to wear in the fall…
Straight-leg denim, a classic white tee, boots, and one of our One/Third jackets. When you live in a city with four seasons, jackets are your outfit, so I’ve always invested in them.
My go-to bag to carry around the city…
My Goyard Anjou (it’s reversible!). I bought it in London, and it’s the quintessential city tote because I throw EVERYTHING and more into it and it still looks chic.
If you see me out around the city, I’m probably wearing these shoes…
These days, it’s the Isabel Marant Denvee western-inspired boots.
Favorite brands for clothing you wear every day…
AGOLDE for denim, One/Third jackets, Everlane cashmere, and Ulla Johnson dresses.
My fall in Chicago bucket list includes…
Whatever new exhibit is at Chicago Art Institute, dining outside for as long as I possibly can (the weather turns quickly), going to a pumpkin farm with my kids, and going to a fall festival in the city (sans kids!).
What to Pack for a Fall Trip to Chicago
Casual Blazer
The One/Third Houndstooth Blazer is a heavy, fall weight — perfect for blustery days.
Comfortable Boots
These Schutz boots have an edge, but are comfy enough to walk around the whole city.
AGOLDE Jeans
AGOLDE is one of my longtime favorite brands; their jeans are so flattering and eventually mold to your body.
An Easy Layer
I love the casualness of Everlane's polo style, but with [a bit of] added elegance.
A Backpack to Carry All Your Essentials
Cuyana makes the chicest leather goods — backpacks are perfect for trekking around the city.
