Last Updated on September 24, 2023
Dressing for spring in Chicago can be tricky. The mornings can be quite chilly while the afternoons are comfortable. And then you can get days like Monday where we had blizzard-like conditions; while today is pushing 60° and sunny. It’s madness. You never know if the snow is gone for good until it hits 90° and even then, it can be a crapshoot. This is how I like to dress in layers.

Photography by Hallie Duesenberg Photography
On location at Presidio Chicago
I’ve found that I’m most comfortable when dressing in layers. My daily wardrobe mainly consists of jeans and a tee, jeans and a button-down. But on workdays, it can walk a fine line between too casual weekend wear. In the mornings, I need to remind myself to add a little something extra to keep warm. A jacket can take casual lounging to a more polished look. Maybe a pair of boots. Add a couple of necklaces and a fun stack of bracelets; now we’re talkin’.
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It’s All About Dressing In Layers For Spring

Jacket (no longer available) /// Shirt (no longer available) /// Jeans (no longer available) /// Backpack /// Boots (no longer available) /// Watch /// Chanel Necklace (vintage)
Looking back on these photos, I wish I wouldn’t have worn these jeans with boots. I always have to be careful with boyfriend jeans. Especially a slim-fit boyfriend. Sometimes they can stretch out and be a bit too baggy, but man, oh man, are they comfy. I think my blue Vans would have worked better. Either that or I should have rolled the jeans.
Rolled or unrolled, I do have to say that MOTHER jeans are the bombdiggetty. Oh, and that backpack, it’s been a love affair ever since it arrived.

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Photography by Hallie Duesenberg Photography
On location at Presidio Chicago

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Nicki
Love! You look great! The backpack rocks too!
kyla
NickiThanks so much Nicki. Hope you’re having a great day!
Crissy
Plaid is my favorite! I love it with your jacket 🙂
Have a great day!!
Ursula
I love plaid too! Here in the PNW dressing for spring requires lots of layering! One minute you are cooking in 65 degree weather, the next minute starts raining 😉 Also, I love your necklaces combo.