What to Wear: Chicago in July

I’m on the plane home from Chicago, already reminiscing about the trip and dreaming about a return journey. I’d certainly make a few tweaks to what I brought along, so let me share with you what I packed that worked and what I’ll bring next time. If you want to check out a few of my staples that might not be on your list, read this blog post, too.

For the plane trip, I always wear the heaviest pair of shoes in my mobile wardrobe. This minimizes the space needed inside bags, and, even if they’re sneakers and they add a few seconds to put back on after TSA, I have found the extra room in my weekender bag worth it. This weekend, I brought two pairs of shoes, the largest of which was my Salomon running shoes, so, Friday night, my travel outfit was a fantastic red sleeveless top from a thrift store, a pair of cut-off shorts from Target, and my trusty Salomons.

I flew from Austin (hottttt) to Chicago (warmish), so summer wardrobe was still the way to go. The next day, we had an active morning planned at the newest of America’s national parks: Indiana Dunes National Park, promoted from national lakeshore to national park just this February (2019). For that outing, I threw on a white tennis skirt (not sure where I picked that up), my Free Fly apparel long sleeve for sun protection, and kicked my shoes off entirely.

This outfit worked well in the city, too, and if you want to see all the places we went follow my blog for more travel posts. This simple book bag here was a Barnes & Noble purchase last summer.

I also brought a date night outfit in my pack. Since it was so hot and we walked everywhere, I wanted to keep things simple, so I threw on my favorite white collared shirt from the men’s department at Gap and a sequined pencil skirt from the thrift store. The red lipstick is (always) Loreal’s Eva shade. (Once again, the shoes were thrown aside as I jumped in Lake Michigan to cool off after a lightly humid summer’s eve.)

My ride or die sunglasses are probably the most expensive things I’ve ever worn: prescription lenses in exaggeratedly large Swarovski frames.

I picked up some swag from Dark Matter Coffee, pictured above and below. I couldn’t resist the heavy flannel that whispers, “Dark matter coffee” in subtle yellow thread and the T-shirt that sports the logo in Spanish, “Materia obscura.”

I fell in love with the city streets, the skyscrapers and the food, the art and the people, the history and the innovation. Next time around, I’ll wear my converse — I hardly ever pack my bags without them, bring a sweatshirt for the plane and cold restaurants, and swap my book bag for a backpack.

What’s your favorite time of year to visit Chicago? I’m dying to see it in all the seasons, although this Texas girl may not be able to handle the cold.

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