Summertime Chi, there’s nothing better! (Well it’s currently raining as I write this, but you know… I guess it’s technically not summer yet.) With the lakefront and beaches so close by, and the countless rooftops and patios all over the city, you spend a lot of time outdoors! Since the city tends to hibernate in the winter, Chicago really does come alive once it warms up. Plans, on plans, on plans… There’s never a dull moment! On any given summer Saturday or Sunday, there are multiple street fests, concerts, parties, and places to be. We tend to spend a lot of time on the move in the summer! And a lot of time sipping rosé alfresco. Or maybe that’s just me… 😉
When you’re going from day to night, it’s essential to have an outfit that can take you from sun and sand to drinks and dinner! I live in dresses all summer long, and thankfully, they’re the easiest thing to dress up or down. Since I’m on the shorter side, I usually opt for a dress that’s above the knee, but I instantly fell in love with this long black maxi dress when I saw it at Express. It’s the perfect blank canvas! It’s a lightweight cotton, hugs your curves in all the right places, and can work for so many different summer occasions depending on what you pair it with. A blue jean or white denim jacket, a statement necklace or even a chic neck scarf or handkerchief, a plaid shirt tied around the waist, flip flops or fancy sandals, a white tee layered underneath, a sweater over your shoulders, a cardigan at the workplace, an embellished jacket over the top to dress it up for evening, you name it! If you know Chicago, you know that it can be W-I-N-D-Y. I can’t tell you the amount of times I’ve had to walk with my arms down at my sides to avoid those embarrassing dress-blowing-up scenarios. When you’re wearing a maxi, though, you’re good!
Last week, I took the afternoon off with Melissa and we headed to North Avenue beach for some much needed Vitamin D and amazing views of the city. We even splurged on a hot dog and a snow-cone! The shaved iced was topped with fruit so that’s all I needed to justify the sweet treat. And I even learned that a Chicago-style dog is everything but ketchup.. ha! The more you know.
Get the Daytime Look…
From there, we wandered back to my neighborhood and stopped at one of my all-time favorite people-watching perches… Gibson’s in the Viagra Triangle. They’ve got intimate outdoor seating in the perfect corner spot, and I can’t get enough of their dirty martinis with blue-cheese-stuffed-olives! So, so good. And they’ve got French rosé, too. My kind of place!
I talked about 90’s trends resurfacing earlier this spring, but I really kind of love how both of these outfits have subtle nods to the 90’s! For the beach, I tied a chambray shirt around my waist, just in case it were to get a little chilly by the waterfront. For drinks, I tied the shirt up into a make-shift denim jacket, threw on a pair of statement earrings, and put on some lipstick. Good to go! I swapped my criss-cross leather slides for a pair of lace-up sandals that are super cute, but still allow for lots of walking. (Ain’t nobody got time for that rush hour traffic in Chicago!)
Also, I ended up wearing this outfit to travel to New York a few weekends ago and it was the best outfit to take me from the plane to wandering around Soho! I wore the chambray shirt on my flight and tied it around my waist for an afternoon in my favorite city. So easy and comfortable, but put-together!
Get the Evening Look…
What are some of your go-to summertime day-to-night outfits?!
Created in partnership with Express