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 :)
- Jul 2, 2019 The best under garments for summer Jul 2, 2019
- Jun 11, 2019 Summer clean out! Shop my closet Jun 11, 2019
- May 2019
- Apr 15, 2019 Miami: Packing, Buying, Eating, Visiting Apr 15, 2019
- March 2019
- Feb 21, 2019 Winter Style Equation Feb 21, 2019
- January 2019
- Dec 30, 2018 A Celebration of 2018's Power Outfits Dec 30, 2018
- November 2018
- Oct 23, 2018 Season Transition is Hard. Seven Reasons it Doesn't Have to Be Oct 23, 2018
- Oct 8, 2018 Five Reasons Why I'm Choosing Jumpsuits Over Dresses (And One Where Dresses Will Always Win) Oct 8, 2018
- Sep 12, 2018 Cape May 2018: Humidity + Wine Sep 12, 2018
- August 2018
- July 2018
- Jun 28, 2018 I Manage My Closet from My Phone Jun 28, 2018
- Jun 13, 2018 A Tropical Vacation to Set my Wardrobe Tone for Summer Jun 13, 2018
- Jun 7, 2018 Sneaker addictions make for good sneaker reviews Jun 7, 2018
- May 25, 2018 A case for finding a forever seamstress May 25, 2018
- May 15, 2018 Monochromatic Style Experiment Turned Love Affair May 15, 2018
- May 9, 2018 Calling all shorties: DYIing your jeans length is so easy! May 9, 2018
- May 1, 2018 When watching TV turns into a shopping habit May 1, 2018
- April 2018
- Mar 20, 2018 White boots: yes or no? Mar 20, 2018
- Feb 21, 2018 Olympic training in Colorado...JK! Annual Sister Ski Trip Feb 21, 2018
- Jan 25, 2018 Seven Unique Ways to Layer Through Winter Jan 25, 2018
- Dec 30, 2017 My 2017 Style Dec 30, 2017
- Nov 5, 2017 The Perfect Leather Jacket Nov 5, 2017
- Oct 18, 2017 I accidentally bought a new wardrobe at Target...again (fall edition) Oct 18, 2017
- Oct 1, 2017 Caring For Your Red Bottoms Oct 1, 2017
- September 2017
- Aug 18, 2017 An outfit tour of London (Part Five) Aug 18, 2017
- Aug 17, 2017 An outfit tour of London (Part Four) Aug 17, 2017
- Aug 16, 2017 A Very Parisian Evening (Part Trois) Aug 16, 2017
- Aug 15, 2017 An outfit tour of Paris (Part Deux) Aug 15, 2017
- Aug 13, 2017 An outfit tour of Paris (Part Une) Aug 13, 2017
- June 2017
- May 2017
- April 2017
- March 2017
- February 2017
- Jan 27, 2017 Love what you wear Jan 27, 2017
- Jan 19, 2017 You can wear leather leggings and these are the ones Jan 19, 2017
- Jan 11, 2017 I wore a sweatshirt to work Jan 11, 2017
- Jan 2, 2017 Winter essential: black tights Jan 2, 2017
- December 2016
- November 2016
- October 2016
- September 2016
- August 2016
- July 2016
- Jun 29, 2016 I accidentally bought a new summer wardrobe at Target Jun 29, 2016
- Jun 20, 2016 Summer in the City Jun 20, 2016
- Jun 15, 2016 What I bought after a month of no shopping Jun 15, 2016
- Jun 9, 2016 My favorite pencil skirt Jun 9, 2016
- Jun 6, 2016 My take on the sleeveless trench Jun 6, 2016
- May 30, 2016 You can never have too many stripes May 30, 2016
- May 23, 2016 Embracing the sneaker trend May 23, 2016
- May 16, 2016 Getting creative May 16, 2016
- May 13, 2016 Bare leg dress weather is here May 13, 2016
- May 10, 2016 Ode to the day-saving peplum May 10, 2016
- May 5, 2016 A vow to not shop May 5, 2016
- May 3, 2016 Let's talk color May 3, 2016
- Apr 29, 2016 Business trip: the next level of planning Apr 29, 2016
- Apr 27, 2016 The great trench adventure Apr 27, 2016
- Apr 26, 2016 This rule is meant to be broken Apr 26, 2016
- Apr 22, 2016 The outfit-making necklace Apr 22, 2016
- Apr 19, 2016 The all-seasons dress Apr 19, 2016
- Apr 15, 2016 Casual Friday Apr 15, 2016
- Apr 13, 2016 The power outfit Apr 13, 2016
- Apr 11, 2016 One shirt, two ways Apr 11, 2016
- Apr 9, 2016 Winter in April Apr 9, 2016
- Apr 4, 2016 Just another Manic Monday Apr 4, 2016
- March 2016