Nine days in the Windy City

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I am finally back in New York and so excited to see my pup and be back into the normal routine after galavanting around Chicago and visiting family. Packing for nine straight days of traveling was a major challenge for me and my crazy outfit rules. As an added twist, almost this entire trip was casual wear. If it had been work wear, I would've gone directly to my four years of well-documented outfit planning in my closet app and easily picked my trusty power outfits for the proper weather and activities. My casual wear is not nearly as well documented...until now!

I usually treat the weekend as off-the-clock, so the same rules aren't followed. I continually revisit the same few outfits, most made up of comfy pieces. For example, this summer I've been living in a pair of loose fitting denim shorts with lots of rips. I pair them with just about everything and wear them almost every weekend. Faced with nine days of casual wear, I was forced to focus on this part of my closet for the first time and quickly come up with some casual power outfits.

My strategy: I started with outfits I had documented as #casualfriday. I then browsed outfits I had worn during the week and came up with ways of making them more casual by pairing them with flats or less flashy jewelry. I committed to packing no heels the whole trip--I never thought I'd say those words! Finally, I started thinking of multiple options for statement pieces. While I already came to terms with checking my bag, I couldn't pack my whole closet, so I included pieces that I could pair with different options and also those that could do double-duty to dress up or down. This doesn't necessarily follow my personal outfit rules, but travel planning is its own beast.

Without meaning to, I noticed that many of the pieces I chose to pack were neutrals, mostly black and white. They are so easy to mix and match and really safe options to add versatility.

This all went down on in my closet app in the packing section where I digitally created outfits.  Some I tried on IRL to confirm they worked, then got to filling the suitcase. I pack by type of clothing--all shirts are stacked and all bottoms are stacked--folding each with lots of extra care to avoid wrinkles.

The main reason for going to Chicago was to get together with coworkers. Since we have several offices and many remote workers, this is one time a year we all get to be in the same place and have some fun. To the Magenta Blazer side of me this was added pressure to look good to people I usually see on camera from the neck up! This is a great time to also thank my super supportive co-workers who listened to me talk about Magenta Blazer all week and take awesome pictures of me for the blog!

Monday: I got in very late Sunday night and crashed. While most people got in early and got a feel for the city, I was starting blind. I went with an exact #casualfriday outfit to start the week safe and comfortable. I noticed other co-workers were wearing sun dresses and shorts, taking notes for outfit planning later in the week.

Tuesday: I love this blue, flowy top. This was one of my statement pieces that I could easily pair with white jeans, shorts or the black skinnies I decided on. These shoes were very walkable, which we did a ton of!

Wednesday: This was the hottest and also the fanciest day of the week, labeled "snappy casual" on our agenda. We topped off the day with an amazing dinner and rooftop party with live music. I went with this black, sleeveless dress with the belted waist because it was the perfect mix of comfort and fancy. These were also the fanciest shoes I brought, which were perfect for standing all night. I got many compliments on my all black ensemble.

Thursday:  Full commitment to white and black casual.  We did a super fun scavenger hunt around the city, so I'm super glad I packed the Adidas Superstars. My team won the hunt!

Friday: We finished the week off with an amazing boat tour on the river, learning about all of the amazing Chicago architecture. Most co-workers were catching flights home later in the day, so I opted for the ultimate in casual with my favorite weekend shorts paired with a light weight white tunic and my rose gold Birkenstocks. Boat-approved outfit!

The second but equally important reason to be in Chicago was to hang out with family. My husband came in for the last few days to see the city (I was basically tour guide at this point. A veteran after a week who even figured out the trains!). The last day we went to Wrigley to see the Mets.

Saturday: The husband made it here late last night! Today we played tourists, visiting Millennium Park and The Bean! We walked everywhere checking out Lake Michigan and strolled along the river walkways. This skirt is too short for work but perfect for a mixed print pairing for a lot of walking. Thank goodness for Superstars! We finished the day with an amazing dinner in the River North area. I wore a multicolored slip dress paired with flat sandals for dinner.

Sunday: We did even more walking, this time along the beach where we stopped for drinks before heading to Lincoln Park. We ended the day at Giardanos for the most intense eating experience--deep dish pizza!  We were warned to wear loose fitting clothes for dinner. I went with a loose fitting off the shoulder top paired with my white jeans--the same from Thursday!

Monday: Needless to say, we needed a break from galavanting. We spent the morning relaxing, then hit a rooftop pool in the afternoon. My slip dress from dinner Saturday night doubled as a bathing suit coverup for the pool! At night, we went to Wrigley field where I obviously had to represent my Mets! I paired my 2015 East Division shirt with my weekend ripped denim shorts and Birkenstocks.

Tuesday: finally time to fly back to New York. At this point I'm hitting the bottom of my suitcase and I want the most comfortable outfit for the plane. I went with my ripped denim shorts for the third time and paired them with the white tank from Monday and my Birkenstocks.

Chicago is a beautiful city. I'm so thankful for the amazing weather, friendly people and ridiculous amounts of delicious food.  I'd say my packing strategy was a success, though I always tend to overpack.  I hope to visit the Windy City again soon, before it gets to cold :)

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