To galavant around the city and its museums, dark pubs, shops, and fine dining establishments, you need to dress for the possibility of anything, which admittedly, can be hard to accomplish. The foundation of this look is a pair of cuffed jeans, graphic tee, blazer, and comfy yet chic flats; however, the add ons are what make it go from day to night with ease!
1. Scarf | We are in the Windy City after all and the temperature from waiting on the "L" platform to entering American Apparel or even while walking on different streets can change drastically.
2. A cross body bag with handles | This allows the ability to passionately talk with your hands about Picasso's paintings and sculptures during your day at the Art Institute, while the handles can be utilized later when you are led to the quiet corner table of a seafood restaurant on the river.
3. Statement Jewelry | Once you have your first glass of wine at Elephant & Castle, it's time to roll up the cuff of your blazer and tuck your hair behind your ears to showcase your bracelets and earrings. Also, consider putting on some lipstick!
|H&M blazer (similar here and here), XXI tee (similar here and here), Gap jeans, Steve Madden purse (similar), vintage bracelets and ring, leopard loafers, purple scarf, Stella & Dot earrings|