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:

… Here’s what I actually took:

Note: I made almost all these clothes myself, including the hand-knits; the print top, sage-green tank top, green cardi, and jeans (although I did add the cuffs) are exceptions. I also made the green necklace. The only items I bought specifically for this trip were the print top, tank top, and metallic wedges. Let me know if you would like information about the patterns.

Here are details on the changes.

I added these:

1. New print top (plus bonus sage-green cotton tank) to replace sadly unwearable print top.

2. Green cotton cardigan for layering (thinking ahead to chilly airplanes, not to mention mosquito-plagued evenings).

3. I decided to take my jeans that I had made over with cuffs; they can be worn rolled down (with bronze metallic cuffs), or up with the lace print shown here.

4. My new metallic wedge shoes. It’s hard to tell in the photo, but the metallic is sort of iridescent; it looks more bronze here, but also has a silvery sheen.

Tip: Metallics almost always function as neutrals in your wardrobe, and can work with casual or dressed-up looks. Versatile!

5. The linen/cotton tweed skirt. In general, I prefer skirts and dresses to wearing pants, so my travel wardrobe felt strangely incomplete without a skirt that could be worn with any of the tops.

6. The green handbag, which is large enough to use as my carry-on bag, but not so large that it would be awkward for normal use. (Packing extra handbags takes up sooo much space.)

I deleted these:

1. The aforementioned unwearable print top.

2. Cropped jeans. They’re lighter-weight than the cuffed jeans, but I thought they’d be less versatile.

3. The bracelet (on the theory that it would be too humid to wear anything close-fitting).

4. The multi-color flat sandals. Although they introduced some fun accent colors into the palette, I thought the other flat sandals would be more useful.

My packing notes:

I could have easily fit this wardrobe into a carry-on, but as it happens, I don’t own a suitcase of the right size; the small carry-on I have would accommodate everything except the shoes. So I used a medium-sized suitcase and had about a third of the space to spare. (This was not really a problem, since we should all be prepared for random acts of shopping while traveling.)

I generally wear my bulkiest items to travel, saving suitcase space; in the summer, this doesn’t apply so much, since most items are lightweight. For this trip, my priority (for the trip to Chicago) was wearing the things that would most likely require ironing if I packed them, e.g. my linen trousers. Here’s what I wore:

Outfit #1 details: This worked surprisingly well. First, I decided to add the cardi (although it was quite hot when I was leaving Portland), and I was very glad to have it, and the silk scarf, on the chilly airplane.

I had been concerned that the linen trousers would get too wrinkled, but what you see in this photo is said trousers after having worn them on the flight out, during the trip, and after they were packed in my suitcase for the trip back! (Yes, they’re wrinkled, but when is linen not wrinkled?)

The cap-sleeved jersey top was extremely comfortable (and a nicely-fitted shape to go with the wide-leg trousers), and I was happy to have the cardigan and scarf on the airplane; I almost always get chilly on board, so it’s a good idea to have a few extra layers.

The shoes also worked out well; I had a little concern about getting through security with them. I usually wear easy-on, easy-off shoes at airports, but these had to be unbuckled— not a problem at all, especially since most airports are nice enough to supply us with benches where we can comfortably put our shoes back on.

My bag turned out to be just the right size, although it did get a little heavy, after adding things like books, my camera, and jewelry that I didn’t want to pack in the suitcase. Speaking of jewelry, I didn’t wear any to the airport, just to cut down on the things I might have to remove going through security (requirements seem to vary).

Conclusion: For a travel-day ensemble, this was quite successful. I was comfortable, both in terms of temperature, and also in the sense of being able to easily move. (If you’ve ever worn tight jeans on a long flight, you’ll know what I’m talking about.) And there was an unexpected bonus to my carrying just the one rather large handbag on the plane: people whose carry-ons will all fit under the seat got to board earlier than those with larger bags!

Note: I wore almost the same thing for the return trip, except I traded the trousers for my cuffed jeans; there will be a photo of this outfit in my final follow-up report (since I’m trying to do this in ORDer of actual wearing).

I think I’ll continue my follow-up report in additional posts, rather than let this one get any longer. Next time, I’ll show you my outfits for at least the first few days I was in Illinois, when I had almost no idea what we would be doing ahead of time; between that uncertainty and trying to find my way around a large part of an unfamiliar state, it was an ongoing exercise in adaptability! Stay tuned!