A Chic Little Winter in Chicago
Chicago in the winter has never needed much introduction.
The lake turns icy. The buildings disappear somewhere between the fog and the clouds. The mornings are crisp and gray, and somehow, the city still looks beautiful.
I was only home for the weekend, which meant there was no real itinerary. Just good clothes, good food, my best friend Mark, and a city I’ve known long enough to enjoy without needing to rush through it.
We started downtown at Millennium Park.
I wore cream from head to toe. Cream coat, cream sweater, cream pants. Completely impractical for wandering around Chicago in the winter, but very cute, which mattered more.
Mark and I spent the morning styling and profiling around the Bean, taking pictures and watching people skate. Families, couples, tourists, Chicagoans. Everybody bundled up and moving around while we stood off to the side people-watching and entertaining ourselves.
Eventually, we made our way toward State Street after grabbing coffee. Past the Chicago Theatre. Through the crowds. Stopping whenever we saw something worth photographing.
Nothing particularly groundbreaking happened. That was the beauty of it.
I love a city day that doesn’t require much from me. Give me a good coat, a hot coffee, somewhere to walk, and somebody I enjoy being around. I’ll figure out the rest.
Birthday, Again
By late afternoon, we made our way to the river for an early dinner at Pizzeria Portofino.
My birthday had already passed, but Mark hadn’t been with me when I celebrated in Atlanta, so naturally, we celebrated again. Why limit a birthday to one day?
We ordered pizza and wine and settled in by the river as the sun started going down over the city. They brought me a birthday treat, we toasted, ate, talked, and watched Chicago slowly shift from afternoon into evening.
There are certain views of this city that will always get me. The river at sunset is one of them.
Sunday Best
The next afternoon called for something a little more polished. Tights. Animal-print shorts. Black turtleneck. Black heels. We went to RL Restaurant on Michigan Avenue for another beautiful meal and, apparently, another opportunity for me to celebrate my birthday.
RL feels like Ralph Lauren imagined as a restaurant, which is exactly what I wanted it to be. Dim lighting. White tablecloths. Roses on the tables. Deep browns and reds. Little touches of animal print. Classic, warm and just old-fashioned enough. It’s the kind of room that makes you sit a little straighter.
They brought out another birthday treat, and at this point, I wasn’t questioning anything. I was simply accepting that my birthday had become a season.
Afterward, we walked around downtown with nowhere particularly urgent to be and eventually found ourselves at the Starbucks Reserve Roastery on Michigan Avenue.
Espresso martinis. Because apparently regular coffee wasn’t dramatic enough for the final stop of the weekend.
And that was it.
A very quick winter weekend in Chicago. No packed schedule. No attempt to see everything. Just walking around my city with my best friend, dressing up, eating well, drinking wine, taking pictures and letting my birthday linger a little longer.
I’ve realized those are often my favorite kinds of trips. I don’t need every weekend away to become an adventure. Sometimes I just want to be somewhere I love, look good, order something delicious and enjoy my own life while it’s happening.
Chicago gave me exactly that.
Cold, chic and just enough.