Her itinerary is essentially a cocktail hour, drinks at a bar and then they are going to see a band. She wants to look stylish and cute, without being too dressy. It's fall in Chicago, so I think sleeves or some layers may be in order, as well as some cute boots.
I came up with 2 ideas for her...1 is a bit of a dressier look. It's a dress with long sleeves that could be paired with some funky print tights (which are very in right now) and some black booties. I also picked some fun accessories to give the LBD a boost.
This Milly dress has an amazing, flattering shape. This is the type of dress you could wear in fall or spring. Available on shopbop.com
paired with these...
Kelsi Daggar boot on Nordstrom.com
and these...
by Anna Beck on charmandchain.com
Or, she could go with a more casual denim look...
Parker top on shopbop.com
Accessorized with...
Torn tuxedo blazer on shopbop.com
For a pop of color, this handbag is adorable by Jennifer Ladd on Etsy
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