Chicago Street Style

Earlier this Spring (2022) I visited friends in Portland and put together a Portland street style video on Instagram, I’ll link it here. No promises that this will be a reoccurring series but I did remember to keep my eyes peeled while I was in Chicago recently and here’s what I saw! Which is your favorite?

7 outfits I saw on the streets of Chicago

The day was 75-80 degrees with some cloud cover but the outfits ranged dramatically from Summer to Fall which I thought was SO fun to see all at once.

The exact outfit I saw was a olive green matching set but I loved the idea of tucking a short sleeve button down into shorts to give the illusion of a romper! Shirt (fits true to size) / Shorts (tts) code Aimee5 / Sandals (tts) and Bag use code Aimee15 for 15% off Able’s website. / Sunglasses

I love to think about where this gorgeous gal was headed in heels and a trench coat, she looked so elegant and I imagine her working at a law firm. Trench (wearing my larger size) / Pants (tts) / Heels are old but I’ll link a similar pair here.

Hands down my favorite outfit I saw and will be re-creating asap! I always think about layering with a contrasting color but I love how she added a layer of the same color as her top - very chic. Linen pants are old but Old Navy brings them back every year (best $30 spent) same pair in flax color. / Tee (size up) / Bag / Sandals are old but I’ll link similar pairs here and here.

This outfit stuck out like a beacon to me because of the BAG, I love a red bag and this combo with green and white looks so good! Jeans are old, heres a similar pair / Tee (tts) / Jacket (wearing my larger size) / Sneakers (size up) / Bag is old but I’ll link a similar one here.

Monochrome is so underrated and always comes off looking chic and put together, the original outfit was worn with brown clogs and a denim jacket slung over the bag. Top (size up) code Aimee15 / Pants (size up) / Necklace code Aimee20 / Shoes and bag are old.

Sleeveless black shirts were EVERYWHERE, I seriously saw so many that it made an impression! Its a great summer basic and so cute with jeans and jewelry. This top is just a t-shirt with the sleeves folded under. Here’s a great, affordable sleeveless tee from an ethical brand. My tee (size up) / Jeans (size up) / Necklace (Aimee20) / similar Sunglasses / Similar sandals linked here and here.

Such a stunner! It’s no surprise that I spotted this outfit because it’s so ME. I hope she was on her way to something fabulous or just enjoying life, either way she was dressed for success! Similar sunglasses / Top (tts) / Jeans (size down) / Shoes are sold out but heres a similar pair.

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Be on the look out for these outfits in motion in an IG reel soon. I’ll be sure to share it here also once its posted. Let me know if you enjoyed this type of post, what do you want to see me style next? Xx