I have successfully survived my first week in Chicago without dying or having some sort of breakdown, so thats good! After a weekend that included a fabulous rooftop bar, a first date, and being a dancing queen at a club, this outfit is perfect for a low key day in the city. Flats for walking, a jacket incase it gets cold, along with a button down which always looks sophisticated and is a very easy piece to wear. A varsity jacket is definitely something to have in your closet for spring. The great thing about them is they are so versatile, you can tone down a really fancy dress by throwing one on or add it to your button down for a sporty feel. I found this one downtown in NYC at one of those like kind of trashy stores… ha, but I had to get it, it was like only twenty dollars! The things you can find if you stumble into the unknown. So this summer when you are traveling, plan your outfits accordingly. It is so easy to be comfortable and fashionable when walking around a city beyond yoga pants, you can do it, I promise.