Moving to the City

Blonde and Bailey, a fashion and lifestyle blogger, in front of the Chicago skyline from North Ave Beach wearing a black pleated skirt and gray top with a Kate Spade handbag.

Let’s talk city life…

This past weekend marked my one year Chicago anniversary. It still doesn’t seem real that I’ve already been here a year. Wasn’t it just yesterday that my dad, Bailey and I loaded up the U-Haul with sugar free Red Bull and Flamin’ Hot Cheetos in hand?

I’ve been looking forward to writing this post for awhile but also have been a little nervous that I wouldn’t be able to put my thoughts and emotions into the perfect words. I guess that’s just the type-A in me.

The truth is, I could never write a blog post that could do this past year justice. But I want to share my experience so here it is, spilling a little bit of my heart (and some funny tidbits along the way) about what I’ve learned from moving to the city. In no particular order…Blonde and Bailey, a fashion and lifestyle blogger, in front of the Chicago skyline from North Ave Beach wearing a black pleated skirt and gray top with a Kate Spade handbag.

I followed my dream. Growing up in Michigan, I came to Chicago about once every year for a visit. I think every trip made me fall more in love with the city. I remember being a little girl dreaming that this would be my life. Everything about it brought me happiness. On a more recent trip, I literally got butterflies when I was in my cab. (I know, why didn’t I Uber?) I needed to do it. I wasn’t living the life I envisioned for myself and my happiness started to fade. I couldn’t give up on my dream and it was started to feel like if I didn’t do something about it now, would I ever?

I’d give up a two-bedroom apartment in a small town for a studio in the city any day. In my defense, I do have good closet space. And I can walk to Michigan Avenue, game over.

I should probably find a new emergency contact besides my mom. She lives about a 4-hour drive from me now, so maybe that’s not the most strategic option anymore…

Hannah Leibinger of Blonde and Bailey, a fashion and lifestyle blogger, in front of the Chicago skyline from North Ave Beach.

Sidewalk rage is REAL and let me tell you, I’ve got it. Just kidding. Somewhat.. I get irritated, I’ve never actually said anything to anybody because life’s too short for that shit. I always thought I was a patient person, though, but apparently this is one of my triggers. I just don’t understand why people stand in the middle of the sidewalk.

I’ve ate more hot dogs and corn dogs than I’d like to admit. Why? WHY? If you’ve ever been out in Old Town with me, you know. You just know.

Blonde and Bailey, a fashion and lifestyle blogger, in front of the Chicago skyline from North Ave Beach.

Public transportation isn’t glamorous. OK, I’m not that naive that I thought it would be, but I’m not going to lie I thought it would maybe be cool to ride the subway. It smells.

4 am bars are a thing. Enough said.

Chicago summers are the best. I spend a LOT of time at the beach and on rooftop decks. The views are surreal and people watching is too entertaining.

Blonde and Bailey, a fashion and lifestyle blogger, in front of the Chicago skyline from North Ave Beach.

You find out who your real friends are. Moving away from most of my closest friends (and family) was hard. Thankfully they understand and still love me. After a year away, I realize my real friends made an effort to stay in contact with me and I love them for it. You know a forever friend when they deal with your daily ugly Snapchats and constant text novels since they’re not here for in-person updates.

You can never take too many photos of the skyline. Or you think you can and have unfollowed me on Instagram.

There are too many restaurants. Lists of places I want to go, lists of places I liked, lists, lists, lists.. too many options. Thank goodness I have Laura who is the restaurant wizard and fills me in on all the best places.

Stan’s and Sprinkles can cure almost all things. The powdered sugar doughnut and red velvet cupcake are my go-tos.

I’m proud of myself. Since moving to the city, I’ve pushed myself to step outside my comfort zone. Whether it’s meeting somebody for drinks, getting through a class in business school, attending a new workout class, starting this blog or 100 other things that could potentially arise, I try to say yes and encourage myself to embrace everything that could be positive (within reason, of course). You’ll never know if you don’t try, right?

Hannah Leibinger of Blonde and Bailey, a fashion and lifestyle blogger, in front of the Chicago skyline from North Ave Beach.

Obviously there’s so much more I’ve learned beyond this short list, but these are some of the best takeaways.

Before I go though, I wanted to say thanks to all of y’all. I can’t express how much all your kind messages and well wishes mean to me. I’m exactly where I need to be right now in life and appreciate all the support. Will I ever leave? Possibly, but probably to another big city. Sorry, mom. 😉

Blonde and Bailey, a fashion and lifestyle blogger, in front of the Chicago skyline from North Ave Beach wearing a black pleated skirt and gray top with a Kate Spade handbag.

Blonde and Bailey, a fashion and lifestyle blogger, in front of the Chicago skyline from North Ave Beach.

Blonde and Bailey, a fashion and lifestyle blogger, in front of the Chicago skyline from North Ave Beach wearing a black pleated skirt and gray top with a Kate Spade handbag.  Blonde and Bailey, a fashion and lifestyle blogger, in front of the Chicago skyline from North Ave Beach.    Blonde and Bailey, a fashion and lifestyle blogger, in front of the Chicago skyline from North Ave Beach wearing a black pleated skirt and gray top with a Kate Spade handbag.      Blonde and Bailey, a fashion and lifestyle blogger, in front of the Chicago skyline from North Ave Beach wearing a black pleated skirt and gray top with a Kate Spade handbag. Blonde and Bailey, a fashion and lifestyle blogger, in front of the Chicago skyline from North Ave Beach wearing a black pleated skirt and gray top with a Kate Spade handbag.

Shirt by Z Supply (I wasn’t kidding when I said I’m obsessed) | Skirt by Nordstrom | Bag by Kate Spade | Shoes by Sam Edelman

Photos by Renee.

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4 Comments

Blonde and Bailey is a Chicago-based fashion and lifestyle blog.

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4 Comments

  • Bri McNamara

    <3 this and you! You've killed this past year and I'm thankful I was able to witness the journey. Proud of you!

  • Renee

    You’re right where you need to be at this point in your life. Your smile tells it all❤️

  • Cindi Whitmer

    Proud of you that you followed your dream. You rocked your first year in Chicago. I was just like you at that age, I wanted more than the small town I lived in. Maybe you have a little bit of me in you, hahaha. Keeping dreaming, keep reaching for more….life is meant to live to the fullest. ❤

  • Kristin

    Your mom willl always be your best emergency contact, even if she is 4 hours away!!! 😁 Love you both! So happy for you Hannah! I loved Chicago so much. Dan and I plan to retire there. Can you still go to Trader todd’s and houndstooth when you’re in your 60s? We’ll find out.

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