In my previous Chicago Travel Wardrobe follow-up posts, I told you about the last-minute print-top switch, and then got started on the follow-up proper, reporting first on what I wore during the trip from home to Chicago (ORD). Now I’ll give you the details: what I did on my trip, what I wore for each event, and how my travel wardrobe worked out overall.

Fair warning: This post will be an extra-large ORDer, served up by your helpful CYC assistant (me).

First, here’s an ultra-brief recap: I met my mother at ORD (O’Hare airport in Chicago), then spent the next 8 days driving her all over Illinois to visit various relatives and friends. Other than her 60th high school reunion, I had no idea until after I arrived what kinds of events to pack for, so my strategy was, quite simply, to opt for versatility over quantity.

There’s a lot of ground to cover, so let’s get right to it, journal-style!

Day 1, Outfit #2: Dinner, evening. Arrived late afternoon at ORD Terminal 3, met mom at Terminal 1. Procured rental car, found way out of ORD maze, and drove north to Libertyville, where we would spend most of our nights with my aunt and uncle (Tom’s my mom’s brother). Was obviously still wearing airport ensemble (Outfit #1), but made slight changes before dinner: removed cardi, added green necklace.

Day 2, Outfit #3: Museum, morning. Aunt and uncle suggested at breakfast that we drive up to Kenosha, Wisconsin, to see a Civil War museum they had spotted while on a bike ride. Turned out to be located right on Lake Michigan, on a slightly chilly, muggy day. I wore my jeans (with cuffs up), and the print top layered over the sage-green tank, with flat ankle-tie sandals:

Tip: Want to see how I changed my jeans to have the convertible cuffs? Click here for Part 1, and Part 2!

Day 2, Outfit #4: Mom’s 60th high school reunion, evening. Mom had said this was being held at a place called The Onion Pub, which on the face of it, doesn’t sound as though it has a formal dress code. So in trying to strike a balance between being simultaneously comfortable, festive, and appropriate, I wore this dress:

Day 3, Outfit #5: 4th of July parade, morning. We drove to a neighboring town for this, then had to walk a fair distance from where we parked. And of course we were on our feet continuously for a couple of hours, so even my extremely comfortable wedge shoes started feeling the strain towards the end. But thanks to an extra dose of sunblock, I managed quite well in this:

Day 3, Outfit #6: Barbecue, afternoon. After a quick lunch at aunt/uncle’s house, we drove to their friends’ home for a barbecue get-together, with about a dozen people. I kept it simple, wearing the same thing as for the parade, just changing into my flat ankle-tie sandals (as in Outfit #3).

Day 3, Outfit #7: Fireworks, evening. I was unprepared for the mosquito onslaught after sunset. All I could do was roll down the cuffs of my jeans, in the hope that at least my ankles would escape unscathed. (Sadly, no.)

Day 4, Outfit #8: Drive to Champaign, early morning. This was nearly 200 miles each way, so we would be spending the night at a family friend’s house. We left early, since the plan was to arrive in time for lunch, at the home of the woman who had for years been the director of a museum founded in the late 1960s by my grandfather. She has recently retired, but lives very near the museum, and she wanted to take us on a tour to show us all the changes and improvements being made.

After lunch and seeing the museum, we would be driving to the other side of Champaign to the house where we’d spend the night.

With the drive, lunch, and museum tour in mind, not to mention that I had to pack for an overnight trip, I wore this:

Day 5, Outfit #9: Drive to Chicago, early morning. The plan was to stop to visit my godmother in Chicago on our way back to Libertyville. Since I had packed as little as possible for the Champaign overnight trip, here’s what I did to Outfit #8 to switch it up: I rolled up the jeans cuffs, put on the print top over the tank top, and packed the cardigan. Done.

Day 6, Outfit #10: Church, early morning. Steamy day. Wanted to be comfortable yet appropriate (uncle said people would be in shorts, something I would never do in public). Result:

Day 6, Outfit #11: Hike in woods, late morning. Okay, I didn’t bring anything that resembled hiking gear, but I thought I’d be okay as long as I covered up with my cardigan (having learned the mosquito lesson). The only problem was my shoes— they were comfortable until we got somewhere around the second mile, then I started developing a blister where the part goes between the toes. Not fun. But it was a beautiful walk.

Day 6, Outfit #12: Visit another uncle, afternoon. This involved driving to a nearby town, where we joined my mom’s youngest brother and his new wife (whom I hadn’t met) at their house for a barbecue. After freshening up post-hike, I decided I had just enough energy to change shoes, take off my now-sticky cardi, and put on my turquoise necklace.

Day 7, Outfit #13: Drive/visit, morning-early afternoon. This time we were heading to another small country town to visit the widow of the former pastor of my mother’s church. I decided for the first time to wear the skirt I had brought; I make it a rule to wear everything I bring at least once on a trip, if at all possible, but this particular skirt, I realized too late, was not the perfect choice. However, it worked on this occasion— the lady we visited was living in a retirement community that was a lot more like a luxury hotel, so I, rather surprisingly, did not feel overdressed in this:

Day 7, Outfit #14: Out to dinner, evening. Aunt and uncle took us to dinner, where we met their 2 sons (my cousins) and their wives. Skirt outfit seemed appropriate, with some tweaks:

Day 8, Outfit #15: Leaving for home, early afternoon. After a refreshingly quiet morning,  another cousin came for a quick lunch, then Mom and I drove back to ORD, returned the rental car, and made our way to separate terminals (she was going to Seattle, I was headed back to Portland). My traveling outfit this time was actually almost the same as when I left Portland, the major change being into the jeans:

Now it’s time (finally) for the final verdict on my ORD travel wardrobe!

What worked well:

1. The variety of tops

2. The cuffs-up-or-down jeans

3. The metallic wedges and ankle-tie sandals (voted most versatile and comfortable)

4. The silk scarf (great pop of color, and sun protection for my neck)

5. The linen trousers, especially in the humid weather

6. The blue-green earrings (worn with everything— see #3, below)

What didn’t work so well:

1. The skirt. I did wear it, but I could have done without it. The linen/cotton fabric was good for hot weather, but something about the combination of the color and style of this skirt just didn’t work as well with the tops as I’d hoped. A more summery, casual skirt would have been better, I think.

What I didn’t use at all:

1. The kimono sweater

2. The cotton cowl

3. The fancy earrings (only because I discovered after arrival in ORD that one of the earring backs was missing)

The bottom line:

Overall, I’d say this wardrobe was successful. I certainly never felt that I didn’t have something appropriate to wear for any of the wide variety of occasions I had to dress for on this trip. I used nearly everything I packed, and I never even had to iron anything, so it was low-maintenance and high-versatility— isn’t that like the Holy Grail of travel wardrobing?

In case you were wondering, yes, it was a very full trip! I’m really glad I got to go, though; my mom and I got to spend a lot of time together, since I was driving her around, I got reacquainted with many relatives I hadn’t seen in years, and it was fascinating getting to see some places from her childhood, many of which I’d not seen before.

At my request, Mom has sent me a list of what she packed/wore/didn’t wear on this trip (wish I’d thought to get photos of her clothes while we were together), and this will be in my next post, along with some wonderful photos of her at various locations and events. You’ll love it!