Sun & Sand to Dinner & Drinks

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…

Express Black Maxi Dress
Express Chambray Shirt
Express Round Glitter Sunglasses
Criss Cross Slide Sandals
Straw Tote
Straw Hat

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…

Express Black Maxi Dress
Express Chambray Shirt
Express White Sunglasses
Express Tassel Drop Earrings
Express Critter Ring
Express Lace-Up Sandals
Black Clutch (similar at Express)

What are some of your go-to summertime day-to-night outfits?!

Created in partnership with Express