Much as I do love traveling, between work and, well, work, there were no upcoming trips on my horizon. (I’m watering plants for friends vacationing in Greece at the moment, but that doesn’t really count, except vicariously.)

Until yesterday.

During a casual conversation with my mother, to put a long-ish story in a small-ish nutshell (mixed metaphors and all), I’m now leaving for 8 days in and around Chicago, Illinois— 2 weeks from today!

I’m sure you know what’s coming next. Once I calmed down (slightly) from my initial excitement, yes, the first thing I thought was, “What am I going to wear???”

Hmm. Having lived most of my adult life in Ohio, land of hot, sticky, airless summers, I can immediately cross a few things off my list: anything tight and synthetic. (I actually have very little fitting that description, so it’s no great loss to my travel wardrobe.) What I do need is sunscreen and mosquito repellant. Lots of both. But this doesn’t get me very far in my wardrobe planning. What’s my strategy?

My thought process, relative to this particular trip:

1. I like to travel light. But…

2. I want to look effortlessly chic. At all times. So…

3. I need a few clothes, all of which must be versatile, not to mention cool, easily washable, and requiring minimal (if any) ironing. Not to mention…

4. Everything needs to work with 3 pairs of shoes. Max. Meaning…

5. With everything else that I need to get done prior to departure, realistically, I have to come up with a wardrobe list, including pieces I’ll need to either shop for or make myself, in a week at most.

At this early stage of planning, I’m concentrating on choosing the most versatile pieces. Since this trip will include at least one dress-up event (loosely defined by me as any time I leave my house), I want to have one nice dress, but it should also work for more casual days.

Dresses and skirts are my preference for hot-weather wear (also dating to my Ohio days), so I’ll plan on one skirt; this should work with 3-4 tops, as well as with flat shoes and heels. Sounds like this skirt will be my go-to item for this trip. The tops should include 1 sleeveless/tank, 1 cap/short-sleeved, 1 long-sleeved (for the aforementioned sun/mosquito protection), and 1 that can function as a light jacket/cardi over any of the others.

And I suppose I ought to take a pair of jeans (she said reluctantly). In general, jeans are not my favorite thing, particularly not in sticky weather. Can I get away without them?

Aside: This might be a good time to mention that the purpose of my trip is to basically function as my mother’s personal assistant, securing a rental car, driving, making sure she has all the gluten-and-dairy-free foods she needs, etc. There’s even a possibility that I will accompany her to her 60th high-school reunion! So it’s not like I’m going to be going on hikes or anything where jeans would be appropriate. My point: there’s more than the weather to take into consideration. End of aside.

I also think I should take some sort of wrap or maybe a capelet, something to combat the inevitable aggressive air conditioning (including on the airplane); a pashmina might be just the thing.

That covers the major parts: dress, skirt, tops, shoes, wrap. Yes, there are more, like jewelry, maybe a hat, but I’ll figure those items out after I’ve nailed down the clothes and shoes.

If you happened to see my Santa Fe wardrobe posts from my trip over Labor Day weekend last year, you might remember that I started by creating a color palette; now that I have a handle on the types of pieces (and how many) I’ll need for this 8-day trip, the colors are the next step— more on that in my next ORD wardrobe post!

Wow. Just yesterday morning, I was enjoying my morning coffee with no idea that just minutes later, I would be scheduling a trip to Chicago! Lesson: Be ready! I’d like to use this project as an opportunity to create a sort of travel-wardrobe template, which just might provide a guideline for my wardrobe even when I’m just being chic chez moi.

P.S. I have a fabulous guest blogger lined up and ready to intrigue and amaze you with her own take on travel wardrobe planning— you’ll love her!