Dressing for Chicago winter weather… That was going to be the title of this post. It would have been, too, if it weren’t for the fact that during this entire trip, Chicago Winter decided to turn into Chicago Spring.
We arrived Friday evening, after a week of temperatures in the low teens, to a scene of 14″ of snow on the ground. I was tickled to death to find that the streets and sidewalks were clear. I could have worn flip flops and not had a speck of snow on my toes. The grass, parks, and medians were a different story, and I found a snow pile taller than me in Millennium Park while waiting for brunch on Saturday morning! But that fantastic semi-cold, not-really-a-Chicago-winter-weather experience isn’t what this post is all about- I want to show you what I wore in order to look like I belonged, to stay warm (hmmph), and to stay comfortable.
Friday night, we rolled into town with the intention of doing nothing more than checking into the hotel, eating pizza, and going to bed (we’re such party animals). 4-5 hours in the car called for comfy clothes and sneakers (I’m aware I’m in heels in this pic (Kate Spade), but this was before leaving, while running errands at home), but knowing that I would be walking around from hotel to Giordano’s, possibly to a bar, I still wanted to look slightly cute. I threw on my favorite lightweight sweater, a pair of silk track pants (both Banana Republic), my Coach sneakers (I live in them!), and my silver fox fur around my neck. Walking through town with my overcoat (from J. Crew a couple winters ago), I was incredibly warm, and my feet weren’t remotely aching.
** Friday, before hitting the road **
Saturday was full of food, cocktails, shopping, the parks… I pulled on a pair of gray suede pants, a short-sleeve silky blend tee, (both from Banana Republic), my sneakers, and my raccoon collar. Again, despite the wind chill, with my overcoat on, I was very comfortable. Brunch was at Wildberry Cafe- a hike from the hotel, but on the edge of Millennium Park, and delicious!! While we waited, we walked through the park, watched the ice skaters, and found a fantastic Jaume Plensa piece facing South Michigan Avenue. After brunch, we set off for a day of shopping. Lunch was late and at Pierrot Gourmet.
** proving that either I’m really short or the snow is really high… Or both **
That night, after a quick change of shoes (into heeled booties from Vince Camuto) and a fresh smoky eye (for me. The B didn’t apply any make-up, but he did give his new beard pomade a first run), we made the trek up to The Violet Hour in Wicker Park, decided we were too old to wait in a 50-person long line at a bar, and decided instead to take a walk through the nifty neighborhood before catching a cab back downtown. There, we slipped into Quartino for dinner and drinks.
** a quick change of shoes **
Sunday morning called for room service in bed (which was a must after drinks at Quartino. Yeesh.). Before afternoon tea, we knocked put a couple of appointments in the burbs. Tea at The Langham always offers an opportunity to break out a fun ensemble- in this case, the VC booties over black hose, under a white, lightweight bcbg sweater dress. I may or may not have decided that this was a good opportunity to wear my silver fox as a hat. It was gaudy and I loved it.
** Sunday, after tea **
Yes, that photo is taken in the ladies room of Bloomingdales Home store. Why? Because there is penny tile and stained glass windows in there.
That night, after a brief disco nap (again, we’re old), we headed back out for dinner and drinks at Siena Tavern and after drink drinks at The Berkshire Room. The hosiery came off, the boots went back on, and the hair swooped up into a ponytail. No leg cover, 19 degrees, and I was still perfectly warm.
** less hat and hosiery **
Monday morning, we grabbed breakfast at local joint Sunny Side Up, Cronuts for the road, and a frozen pie from Giordano’s. Easily the coldest day we were in town, I still stayed comfortable in a thin sweater dress, my sneaks (told you- I wear them ALL the time), and a ridiculously oversized scarf from bcbg. I didn’t grab a photo, but it was adorable, I promise. While my legs didn’t go numb while walking the few blocks to and from breakfast, I would have had to have on either tights or leggings if I was spending more than 10 minutes outside.
Folks, I’ve got to tell you that I’m a little disappointed in the weather we experienced- not because it was too cold, or too wet (once the snow started to melt)- but because I wanted to feel winter in Chicago. I wanted to feel the biting wind, to stomp through slush in the streets (I packed my snow boots, I swear). I needed to be a part of the normal Chicago February weather in order to know if I could ever really hack it if we decide to retire up north. I assume I’ll just have to visit again next winter!
While this post is in no way sponsored by anyone mentioned, I would like to give you the opportunity to purchase any of the items that you see and love:
** sweater, silk track pants, sneakers, tee, suede pants, booties, white dress (similar), overcoat (similar) **
