weekend capsule wardrobe: chicago!

Updated: Aug 11, 2018

I'm going to Chicago this week! TBH: Cass and I are going to the Windy City primarily to see Canadian Teen Pop Sensation Shawn Mendes in concert (already crying). We've got a fab itinerary lined up, complete with an architecture tour, a Cubs game, and a show at Second City. (PS. we're still looking for food and bev recommendations!)

We obviously have some wardrobe planning to do - we aren't going to just wing it for such varied activities in such Instagrammable locales! Who do you think we are? (Just a reminder: we are @emmastevens_ and @cassiebrannagan)

We're not checking any bags, so everything needs to fit in my carry-on and backpack. This means every item I pack needs to be intentional and needs to do double duty and work for at least two different outfits. This is in keeping with the capsule wardrobe thinking. If you've ever thought of doing a capsule wardrobe, packing for a short trip is a great test run!

Here's how I'm putting together my Chicago weekend wardrobe:


1. Check the weather forecast. Keep this in mind.

2. Identify activities, outings, venues requiring a change of clothes. I made a table . You don't have to do this. But you totally can if you want to. My activities are:

  • Flying

  • Shawn Mendes (still crying)

  • Walking around town (x3)

  • Dinner and Hamilton (the musical - I know, right?)

  • Cubs game

  • Dinner and Second City

3. Imagine your outfits for each activity. Here are some questions to ask yourself as you go:

  • Will I be hot or cold at this activity?

  • Pants or no pants?

  • How fancy should I be?

  • What kind of footwear do I need?

  • Will I buy a souvenir t-shirt at this activity (ahem* Shawn Mendes *ahem) and wear it the rest of the weekend, thus rendering this exercise useless? (Probably.)

4. Lay out your outfits. It helps to see everything in front of you.

5. Now edit. Some questions to ask yourself:

  • Can this item of clothing work for at least two outfits?

  • Is now really the time to try to break in shoes you've literally never worn before but now feel you must absolutely have on this trip?

  • Do I really need all the purses?


1. Pack clean clothes. Do some laundry if you have to. You're worth it.

2. Take some tips on how to effectively pack a suitcase 

Here's what I ended up with in my weekend wardrobe.

Total activities requiring an outfit: 8

Bottoms (4): Black jeans, leggings, blue jeans, leather skirt

Tops (4): White tee, 'nope' leotard, white pull-over,

Shoes (3): Sandals, heels, leather sneaks

Outerwear (2): Leather jacket, jean jacket

Do you guys have any tips for planning clothes for a short trip? What basic pieces do you use for multiple outfits?


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