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:

  
  

#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:

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?

“Chicago is an October sort of city even in spring.”
— Nelson Algren, Newsweek, August 13, 1984 (photo via)

No matter how many times I do it, I always get excited about taking a plane trip.

Some people only like the destination part of a trip – cough*Daniel*cough – but not me! The planning, the packing, the journey to get there, the destination itself – I love it all. (Minus the unpacking and the laundry to do when you get home.)

In less than TWO WEEKS, I’ll be in Chicago for an extended family weekend with my cousin and sister, and I really couldn’t be more excited about it. I wish Daniel could come too, but I can’t wait to explore the city with my girls! I’m the type of person that as soon as I know a specific place I’m visiting, I start planning every minute of my trip, from packing lists to the food to the must-see destinations. And, in true Pinterest fashion, I’ve been busily pinning lots of pictures of “Chicago style,” few of which actually include clothing items I already own…*oops*

I’m still working on an outfit packing list, but here’s a few pieces of inspiration. I am a packing fiend – I love figuring out how to maximize what I pack while minimizing the amount of space it takes up. Anyone else out there like that, or am I alone in my fiendish-ness?

   
   
(From top left to bottom right: 1. pin, source; 2. pin, source; 3. pin, source was Sevenly, image no longer available; 4. pin, source; 5. pin, source; 6. pin, source)

I’ll keep you posted on my outfit choices!

I was feeling extra hipster this weekend so I checked out this article:

(Pin photo via Condé Nast Traveler, article source here)

I’m not really that hipster, you guys. I could lie and be all, “Oh, I don’t want to look like a tourist,” but the truth is I really don’t care what’s considered “touristy.” I’ve been to Chicago before, but it was nearly 10 years ago when I went with the Oklahoma Baptist Youth Choir and Orchestra (which makes me sound stupid old), so it’s been awhile. We visited a lot of popular places, but I enjoyed them, so who cares?

The biggest differences between that trip and this trip are: (1) more freedom as far as itinerary, (2) staying in the city as opposed to outside of it, and (3) I’M A GIANT FOODIE NOW. It’s a little sad how excited I get about food. I’m at the mercy of the people I’m traveling with, of course, but I’m hoping we can visit some neat little local places instead of stuff we could easily get back home.

Even though I’ve been to a few of these already, here’s my top 5 hopefuls for the trip:

• Shedd Aquarium – the largest indoor aquarium in the world
• John Hancock Observatory – the best 360 view of the city
• Pequod’s Pizza in Lincoln Park – called “the deep-dish pizza locals actually eat”
• Any of Thrillist’s 10 Best New Burgers in Chicago
• Millennium Park – lots of cool packed into one city block

If you’ve been to Chicago before – what was your favorite place you visited?

Save