In my first follow-up report on my Chicago (ORD) travel wardrobe, I told you about a last-minute fix for a minor packing-related emergency. Now I want to get on to the follow-up proper, starting with showing you exactly what I took with me; as you’ll see, I made some switches from my original plan. I’ll show my outfits, in the order (ORDer?) in which I wore them, and also with details about what I wore them to do. (Just so this post won’t swell to epic proportions, I’ll split this part of my report into 2-3 posts, each covering a few days of my 8-day trip.)

Aside: I should tell you that the reason for my trip was to accompany my mother (after meeting her at the airport in Chicago) through 8 days of driving around a fairly big area of Illinois. I did all the driving, and basically acted as a personal assistant. However, other than my mom’s 60th high school reunion, I had no idea what types of events I’d need to dress for; all I knew was that we were going to spend a lot of time driving, alternated with visiting Mom’s relatives and family friends (most of whom I hadn’t seen for literally decades). I did have some idea of what to expect weather-wise, having lived in Ohio for almost 25 years before moving back to the Pacific Northwest (in a nutshell, humidity and mosquitoes). Since I was really just guessing as to what clothes I would need, I decided the best approach was to make each piece as versatile as possible, namely, separates, coordinated through the development of my wardrobe color palette. End of aside.

Before I flew off to the Great Midwest, this was my wardrobe plan:

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