Packed: Chicago Picks

With my extended weekend just two days away, I figured I should finally start thinking about packing. I’m usually a big packing list maker, but the last few weeks were pretty full and this trip really snuck up on me! Two days early is the best I can do this time around to try to “prevent that last minute pack everything I own business,” as my traveling buddy Jennifer put it. (Which – let’s be honest – I will probably do anyway.)

I’m a big fan of basic mix-and-match essential pieces like:

•  a striped tee
•  printed shorts
•  skinny jeans
•  a structured dress
•  strappy wedge heels

Most of my packing lists include combinations of items like this, along with other accessories like a statement necklace or a wide-brimmed fedora. As I mentioned before in my first post about this trip, I’m not really concerned about looking like a tourist – I have no plans to pack any fanny packs or ugly printed t-shirts. But it is important to me that I genuinely love each outfit I wear when I travel, regardless of how casual or fancy-pants it is.

For a four-day trip, including travel days, here’s a few outfits I came up with:

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#1: Plane travel outfit. Comfy skinny jeans, slip-on shoes for security, and a cardigan in case of crazy-AC-blasting seatmates on the flight.
#2: Walking the city streets. Light blue oxford, belted shorts, and a statement necklace for a little frosting.
#3: Dressy night out. Little black dress, pearl cluster necklace, and leather wedges.
#4: Extras. A grey tee, striped tee, printed tee, floral scarf, leather flats, and my favorite J.A.C. jeggings – easy pieces to swap in if need be.

As for my on-flight essentials:

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Fossil wallet – because money and identity are important when flying.
Sunglasses – my new pair has tortoiseshell upper rims!
ModelCo Party Proof Lipstick in Kitty – the perfect nude lip color.
Real Simple magazine – one of my favorites.
Headband – for when you are just done with your hair being down.
Mini portable phone charger – holds enough power for a full phone charge!
Pen – because pens are always good to have.
Jergens BB Body Lotion – for dry skin at high altitudes.
Hand sanitizer – because people are gross.
Headphones – so you can watch a movie or pretend to be busy.
English Laundry Eau de Parfum rollerball – when you need a little smelly-good stuff.
My Future Listography – because this book makes the list-maker in me giddy.
Osprey Daylite Daypack – perfect backpack for day trips.

I’m almost all packed, but I need help with one little thing. I can’t decide whether to pair this tank with mint or navy shorts. What do you think? Help me decide!


What’s your vote: mint, or navy? Also – what are your packing list must-haves when you travel?

5 thoughts on “Packed: Chicago Picks

  1. Sam Nungester says:

    Both! Definitely both! Decide that day which ones to wear- mint green for a fun day and navy for a more casual day!


  2. Aunt Jackie says:

    No matter what you decide, you’ll look cute. You can always pull off outfits right out of fashion magazines.
    P.S. I am really enjoying your blog. It’s a perfect thing for you to do. Lovin it!!and love you too🍕🍦🎉⚾️🎶🚖✈️😎😘


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