This was the beginning of my weekend jaunt to Chicago. We stayed at the Trump Hotel and just like our stay a few years ago it was excellent. I wore this outfit on the plane and I finally got to use my Pendleton weekender bag that I bought a year or so ago from Free People. I pack pretty light using a Tumi carry-on suitcase and the Pendleton bag. I like to challenge myself in terms of re-wearing the same pieces in different ways. The J Brand jeans proved to be pretty comfortable for the trip due to their high waist. I wore them with this super soft micro modal tee that I snagged for under $50 from the Outnet. Kimberly Ovitz sure knows how to make a t-shirt. This is by far my favorite tee and I wore the heck out of it all weekend. The leather motorcycle jacket was a must since it was freezing and windy in Chicago. This thing is pretty tough and one of my co-workers at dinner actually thought I rode in on a motorcycle. I needed some good walking shoes that still looked cute and had a heel so the Camilla Skovgaard cuban booties came in pretty handy. We had dinner at Hugo's the first night and it was delicious. There wasn't an empty seat in there and I can see why. If you ever want seafood in Chicago I would highly recommend Hugo's. I had the crabmeat avocado as an appetizer and then the Chilean seabass as my main course. Stay tuned for more photos from my trip!