Travel Packing for this Dummy

Am I the only one who has a moment of panic when packing for an upcoming trip? Suddenly everything in my closet is wrong. My shoes. My tops. My accessories. It is ridiculous. I don’t know why, but more times than not, before a trip I feel the need to go shopping. Which is completely backwards if you think about it – you’re going away to see people who you either don’t know at all or who rarely see you and therefore have no idea what is new versus your go-to tried-and-true outfits. It’s the people at home who realize you wear the exact same dress every Wednesday.

The husband and I are heading to Chicago tomorrow for four days and three nights of childfree adventure. I’m perhaps most looking forward to 3 nights of uninterrupted sleep. But I’m also excited about the fact that we’re going to one of my favorite cities. I LOVE Chicago. One day I hope we live in a condo in the middle of all the hustle and bustle. At this point it will have to wait until we’re empty nesters because this girl is not going back to city living anytime soon. But when we do, I picture us in Chicago. I love that it’s a real, walkable city. There is just something about the Windy City that sets this girls heart afloat. I don’t know if it’s because it’s my man’s hometown. Or the fact that I’ve never been to NYC so I can’t compare the two. But I adore Chicago. I love walking down Michigan Avenue. I love going down to Navy Pier and sightseeing on a boat tour or just taking in the sights. I love the shopping. I love the museums (we have the Art Institute on schedule for Friday, which I’ve never been to!). I even love riding the train. And who doesn’t love taking in a Cubs game?! Or grabbing a drink at the top of the Cock.

Admittedly, I don’t heart all these things in the winter quite as much, but one of my favorite trips was in December when my now-husband, then-boyfriend and I had only been dating a year.  We went up for his father’s retirement party and I was gifted tickets to Wicked by his parents as an early Christmas present. So after the retirement lunch at Bucket of Pepto, we strolled around the city with a stop in Marshall Fields for me to buy new shoes to replace the uncomfortable 4 inch wedges I thought were a good idea on the plane. We ate dinner at some diner, walked around an outdoor Christmas bonanza and then took in the show. It was a perfect day, even with the wind chill.

But that bad shoe choice has stuck with me. So now whenever we go to Chicago, I know we’re going to be walking much more than normal and I always feel my shoes are all wrong – I want them cute yet comfortable, which obviously I don’t own (for those that don’t’ know, I have a bit of a shoe obsession and have more shoes than is necessary). But you can’t buy a new pair of shoes a day before a trip and expect to not have blisters from wearing them all over the city. And the reality is that my current shoes are just fine. But my head gets all worried that I have the wrong stuff.  I think it’s the whole issue of only being able to bring a few things and then worrying I’ll hate what I brought and regret my choices.

I’m sounding more nuts as I continue, aren’t I?

Well, I went out and bought a bunch of new Spring tops this weekend. (Marshalls is my go-to store. I bought 6 tops and a pair of white jeans for under $160. So at least I’m a thrifty gal.  I did walk away from 2 killer Diane von Furstenberg dresses that I’m already regretting though.  Aren’t they cute? Yes I text my mom while in a dressing room. What of it?) So I have a bunch of new cutesy tops to wear this weekend, only problem is the high is about 52 each day we’ll be there.  So it’s my old, go-to sweaters to the rescue.

Moral of the story: Wear what you got girl. And don't look so angry in dressing room selfies.  Also, wear makeup and brush your hair.  Life lessons I'm clearly still learning.