Back in Chicago

What to wear in the spring when spring is 58 degrees + my complicated relationship with Chicago

I’m officially back in Chicago. When you’ve lived somewhere for 20 years, leaving for 7 months feels like a blip. I’m typing this at the same coffee shop, Damn Fine, in Logan Square, that I’ve been working at for the last five years. There’s something really comforting about familiarity, but on the flip side, “familiarity breeds contempt,” as Taylor says.

I think of how Carrie Bradshaw described her relationship with New York as I think about my relationship with Chicago. It’s complicated. More on that later.

In the meantime, let’s talk about getting dressed. As I type this, the high today is 58. And it’s cloudy. Has anyone figured out how to dress in Chicago in spring? I sure haven’t. Getting dressed today I just stared at my closet thinking, “where are all my spring clothes"? Oh - Chicago has like 3 days of spring, so I don’t really have “spring clothes”. It’s May. I looked back in my camera to see what I wore last year at this time and here are 5 looks I will recreate.

Some takeaways:

• Really good outerwear - this is my trench, the denim coat is vintage, and I am currently wearing this duster that is on sale (best purchase ever).

• Sweaters over dresses. You may recognize the Mirth dress that I’ve been wearing in Florida. This is how I’ll style it in spring.

• Great basics. This may seem obvious, but I am wearing the same black long sleeve today that I’m wearing in the pic above and I can tell you a good tee goes a long way. And so does good denim and a classic button down.

• Birkenstock clogs…wear them with socks or without. I’m also wearing these a lot.

• A bag with some personality. I love wearing the Croco Sling Bag over something really minimal. It just adds a lot to the whole look. Aaannnddd…a small batch of French Blue is dropping very soon!

Thought of the week

This was a James Clear post that I saved on Instagram. It really hit me. Most of life is process. Whether it’s work related, raising kids, dating, planning a trip…most of life is in the “in between” not at the destination. We have to either find ways to love the process at hand or change the goal because he’s right, otherwise we’re guaranteeing disappointment for ourselves. I am going to challenge myself to think about this the next time I feel disappointed about something to see if I’m falling in this trap.

Ok back to my complicated relationship with Chicago.