what I wore for Chicago rain and snow
when I no longer have a puffy coat and HEATTECH essentials
So I realized while waiting at O’ Hare for take off back to LAX that I left my laptop charger back in the hotel room. I was planning on a detailed post about what I bought and wore on my Chicago trip this past week, but I will share what I wore instead. And I was not prepared for the rain and snow in the three days we were there.
I lived in New York City for two years from 2011 to 2013, and then in the D.C. area after that for just under a year, so rain, snow, and wind are no strangers to me. But I no longer had my puffy jacket and Uniqlo HEATTECH essentials throughout the years my wardrobe changed and evolved. I wasn’t interested in buying brand new fall/winter pieces in the middle of spring. And as we were nearing the end of our seven week (originally slated to be 4-6 weeks) home renovation project I was ready to settle in and enjoy our home in peace.
There is one tried and true technique to dressing for unexpected rain and snow
Layering clothes, accessories, even layering hair is not new, but it’s effective. It’s a styling trick that is versatile and fun, and stands the test of time. Instead of buying new pieces I decided to follow Allison Bornstein’s recommendation and shop my own closet.
My thickest and warmest coats are wool, so naturally I felt my Max Mara Poldo coat1 was essential. It’s one of the first things I packed for my trip. And because it is so long, I can easily use it as a blanket in flight.
I don’t have a beanie anymore, but I do have a hand knit adult bonnet in dark red that I purchased from July Knits on Etsy. It is 100% wool and such a fun, cute twist to a fall/winter look. The best part of it was supporting a small business overseas, which I am always glad to do.


To switch up my head accessory, I wore my Dakin hood for the first day and a half in Chicago while exploring West Loop and Lincoln Park. I personally love pieces that come in one size, so the hood (made from pure merino wool and super warm), was definitely a no brainer to buy.
I made sure to wear a combination of wool, cashmere, and nylon to stay relatively comfortable
On my outings I always wore my Wolford body suit (this one made from 86% nylon, 14% elastane is my favorite) and layered it under a cashmere sweater. On day 3 it started snowing briefly, so I wore my satin tights (it was finally a chance to wear my Sergio Rossi x Wolford red tights to brace the cold) under my jeans (my go-to is Levi’s, but while shopping around on Armitage in Lincoln Park I found myself in front of a Jenni Kayne boutique, where they had Agolde denim. The cropped Ren jean fit so well I bought it without hesitation. I eventually wore it on the flight back home).

I noticed that aside from one man who was walking his dog, I didn’t see a single person wearing gloves (including my good friend, who has been living in Chicago for the past five years). I was barely acclimated to the midwestern rain and snow in the few days I was there. The cashmere lined leather gloves from Vince2 kept my hands warm, and these never left my nylon Le Pliage Longchamp tote, which I carried everywhere.
As for socks, I packed a pair of cashmere socks but I didn’t wear them because they were too thick for the Essen glove boots I wore to walk all over West Loop, Lincoln Park, Wicker Park, and Andersonville. Except for a few scuff marks on the heel and toe, I am so amazed at how well they held up throughout my trip.
Thankfully I didn’t have to buy an umbrella; the hotel let me borrow one of theirs for a whole day.
While lounging around in my hotel room this mariner jersey tee was super cozy.
Share in the comments how you keep warm in colder climates. I would love to know what your tips and tricks are.
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