What to Wear Downtown

I grew up in southern Indiana, and while I was near a suburban area, my upbringing was largely rural. When you are from a smaller town or rural area, visiting a major urban area (like downtown Chicago) can seem so daunting!

I have friends coming to town this weekend, and as I am telling them what to bring, I am planning my own necessities for spending several days downtown.

What to wear:

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This jacket is my go to for any trip- urban or rural. It is perfect for city trekking because it comes in any color, it has pit zips so you can wear it inside or in warmer months without sweltering, it is waterproof, and the best part: it folds into it the pocket. When it is packed into the pocket and zipped up, it is smaller than a paperback book, which is perfect for tossing in a bucket bag or daypack.

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In the city, it is totally okay to wear any wild and crazy color that you feel compelled to wear! Admittedly, I gravitate towards gray and black these days. Black jeans are easy to wear with any top or shoe, and wearing dark neutrals is the fastest way to feel sleek and pulled together.

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Sometimes in the park or in a theater, it can get pretty chilly- even if it was an otherwise warm day. It is crucial to pack an extra sweater or fleece, even if it was warm when you left! I was kicking myself during brunch on the patio last week when the sun went behind the clouds and the temperature suddenly dropped ten degrees! Please take an extra layer.

Walking: 

#1 Rookie mistake: wearing cute flats downtown. Locals cringe when they told their friends to wear tennis shoes and they shoe up in flats or flimsy sandals… or heels!

Here’s why:

  1. You will be walking to the train and to the bus and to shops and museums and through shops and museums and up stairs and down ramps and will run to catch the train or cross the street and stand still waiting in line… your feet will be killing you even if you wear your best, most supportive shoes. So wear your best, most supportive shoes.
  2. You shoes are going to get a little nasty. People pee in these streets, and worse. Seriously. If you have sandals or flats your feet will be as dirty as the bottoms of your shoes. Keep this in mind! When I wear sandals downtown, I am sure to choose a pair that is about an inch off the ground (still a flat, but with a slight elevation.) These flatforms are probably a great way to navigate the city!
  3. The weather can be different in each neighborhood. Even when it is sunny with clear, blue skies at my apartment, it can end up being cold and rainy downtown or in another neighborhood. When it is raining, some parts or the street or subway flood. Rain boots you can walk in are essential.
  4. Sometimes you want nice shoes. It is okay to wear flats or heels to the show you are seeing or party you are going to. Just take them with you, in your bag, and change when you arrive. Anyone who works in the is going to wear sneakers to work and change when they get there. When in Rome…

Carry-all:

You need something to carry your wallet, extra sweater, rain jacket, flats, external battery, water bottle, and snacks in. This reversible option is my favorite! _9512099.jpg

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