We have a good handle (and a good system) for riding the “L” so we don’t look too foolish for that part of our journey. Unfortunately, we are still at a stage where we need a double stroller, so we stand out a little bit, but that just can’t be helped until little legs get a bit stronger at our house.
My only option then is to make sure I dress like a native instead of a tourist. I make sure never to wear tennis shoes, particularly white ones, if I can at all help it. If I can handle wearing heels for a day of hard walking, that is a major plus.
If you want to fit in, wearing black is not necessary, but always safe. Oddly enough, in the winter you can actually wear scarves, hats and gloves. If there is one thing a native knows, it is the fact that it always colder downtown. The wind will blow right through you if you aren’t properly dressed.
Other than wearing black, I’m not exactly sure how to describe the best way to dress. Maybe it is simply easier to describe what not to wear.
If you really want to fit in like a native in downtown Chicago, if you don’t want to be instantly pegged as a tourist, absolutely, positively, never ever wear your out-of-state team colors for a day downtown. And especially make sure you don’t dress your entire family in the same out-of-state-team color.
Particularly if that particular color happens to be day-glo orange!
(At least we never lost anyone!)