Back to the city that holds a special place in my heart, Chicago! My family originally moved here from a small village in Bulgaria back when I was just a little girl, and we lived in Chicago for our first 4 years in the USA. This time around I finally got the chance to explore Downtown Chicago by foot (the best part…walking everywhere) and had so much FUN!

I CAN’T WAIT to do a future travel post of things to see in Chicago, but in today’s post we’ll focus on the style only. I was so inspired strolling around and people watching in this city because it seemed like everybody had a super cool and unique style. It was a head turning experience for me because we don’t get that as much at home in the Las Vegas heat. It was so hard not to STARE. I only stared because I loved everyone’s outfits. hahaha!

If you know Chicago, you’ll know how quickly the weather there can change. One minute it can be sunny, the next it can be raining heavily. This time I was very well prepared with my wardrobe. We visited in early September, and so I packed an umbrella, a jacket, a few hats, shorts and tees. In the end I used them ALL!

Here is a selection of the outfits I wore in Chicago! Enjoy!!!

DAY ONE

On our first day the weather was sunny, bright and beautiful. Just the kind of welcome I had hoped for, true bliss! I was in the mood to explore lots, and to do so wearing my happy yellow bodysuit. I felt completely in sync with the larger than life Chicago vibes.

Before this trip I had done some online autumn shopping (as one should), and that’s when these plaid pants graced my cart. I completely love the style, the fit and the comfort. They are stretchy and easy to walk in just like your comfiest sweatpants. As I write, I’m really looking forward to our “Vegas autumn” coming later in October, so I can wear them again and again!

Packing for a trip with a single carry-on bag can be tricky, and I had to make the almost impossible decision of picking only two pairs of shoes. One pair had to be these vibrant red sneakers. I think they give each outfit a little something special, and I love wearing something red no matter if it’s accessories, lipstick or clothing. Red is my color!

DAY TWO

This day was spent exploring Downtown Chicago further and I wanted to keep the comfortable, versatile style going. It’s always a good idea to have a sweater on hand while taking a long walk by Lake Michigan, as The Windy City has a way of surprising you with some BIG gusts!

One thing I love about this outfit is that I’m wearing my whole heart, and my love for Chicago, on my t-shirt. I can’t begin to explain how happy I am to have visited again. Next time I want to fully embrace the Chicago winter – even though I don’t yet have the wardrobe for it!

You have probably already noticed in all of my daily Chicago looks, I carry my Travelon crossbody bag. It’s the BEST! All your belongings will be safe as it’s designed with anti-theft features in mind! I always feel super safe when wearing it. I chose a darker gray color so it doesn’t stand out so much. I’ve had it for a year and haven’t traveled with any other bag since.

DAY THREE

The star piece of this outfit is my cardigan, which always seems to receive a compliment or two. It’s the fuzziest, cutest thing like a favorite blanket. And it’s just what I needed for the cool morning air.

I think this outfit could be my favorite. Something about the colors, the balance and the way it made me feel. By this day I was adjusted to the city and feeling extra confident, and it was becoming easier to put different pieces together with the changing weather in mind.

DAY FOUR

This day was the hottest of them all and we decided to get out of the city. We took the morning train to Indiana and embarked on a day-trip to Michigan City, where we hit the beach and enjoyed the most beautiful and calming lighthouse views. Unfortunately I didn’t pack a swimsuit, but at least I was able to wet my thick curls under the outdoor shower. That made the long hot walk back to the train station more pleasant. hahaha!

Here the crop top and button down shirt saved me. I was able to face the heat as the shirt is a cool and breathable linen. I had the genius idea of turning my pants into shorts by pulling them up to my knees. The magic of travel fashion! haha!

DAY FIVE

As a sign for our trip coming to an end, the last two days in Chicago were windy and rainy. This is why I had to pull out the warm hats, the jacket, my yellow umbrella which almost flew out of my hand…you get the picture.

I don’t often show off my travel airport looks. Here we are…DRUMROLL! The comfiest, coziest vibe from O’Hare Airport. Honestly, it was so easy to fall asleep in this outfit. I do really enjoy seeing what people wear when passing through the airport. How about you?

With this outfit it’s time to say goodbye to Chicago, until next time! Which one is your favorite?