Loyal reader Mawuli Grant Agbefe reached out this week offering to write a piece on dressing in Chicago when it’s not supposed to be winter, but isn’t exactly spring yet. He was advised to write the piece quickly, before the weather turned, and he did.
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This week I faced the dilemma of dressing too warmly. Blue Lands’ End OCBD, zipped hoodie, Nantucket Reds and LL Bean duck boots. The coat was a light raincoat, but with the hoodie on underneath, walking to my afternoon sushi and to and fro on Chicago’s transit system definitely had me breaking a sweat. In my college years I had the opposite problem. Mornings would be chilly and below 50, but by the afternoon it would be quite warm. I’d start the morning shivering in shorts with some kind of polo/parka/sweatshirt combination.
The temperature dropped by 20 degrees today, so I broke out the grey flannel trousers with blue OCBD, navy blazer, penny loafers and Mackinaw coat. It’s a winter coat made by J. Peterman, though Filson and other brands make them. It’s rugged but not too heavy. I recently purchased a pair of madras pants and floral go-to-hell pants in anticipation of when the weather actually is consistently warm. I’ve delayed getting a new pair of boat shoes, but have my eye on a Nantucket Red shade from Sperry. Seems like they’re going in a new direction with laces that aren’t rawhide, or no laces altogether. But despite the temperature fluctuations over the past 30 days in Chicago, one thing has remained my constant. My navy and green grosgrain belt from Barron’s Hunter.
In the meantime I plan to grab the significantly shorter LL Bean rubber mocs, which are good for the time of year when it’s raining but not snowing. By the end of the day, with the regular Bean boots on and heavy socks my feet can be kinda sweaty. That’s heavy-duty Ivy, and not in a good way. — MAWULI GRANT AGBEFE
Enjoyed your take. Living in Newport, I often face the same challenge. A nice read!
Where was the photo taken?
Quite-Spring and Edition don’t show up on the preview in my browser, and that paints a whole different picture…
Sir, you deserve a medal for enduring Chicago winters, with oak leaf clusters for doing so in style.
In front of the Art Institute, I love the coat. Chi-town a great city to visit, one of my favs. Thanks Mawuli!
Broke out the madras and seersucker Easter. Temps in the 80’s here in San Antonio. Don’t think I could live where they have a real winter.
While Chicago is a wonderful city and the Art Institute is a world class art museum, this post confirms the wisdom of my decision some 50+ years ago to leave the Windy City and head south.
Nice post, Mr. Agbefe
It has been similarly cool and rainy in Boston for weeks now, and I for one have been enjoying keeping the tweed, corduroy, and flannel flags flying a little later into Spring than is sometimes prudent.
Chicago is known as the Windy City, but Boston, where I live, is windier. You definitely have to have four different sets of clothes and and shoes for each season unless you want to look like a tourist.
I plan to break out my Sperry topsiders (worn sockless), seersucker, and madras as soon as the weather changes from cold and rainy.
Another Bostonian chiming in to claim the “Windy City” moniker. The corner of Boylston and Tremont is murder from December until May.
Chicago does get windy but it was deemed the windy city because of the blustery way people talk about it and the hot air the politicians blow around.
Marcantonio, the pic was taken on the front steps of the Chicago Art Institute Museum on Michigan Avenue (the showcase street In Chi).The view is north; Lake Michigan is about 2km to the right.
I know what Midwest winters are like. We get that very cold day followed by 45 degrees and sunny with rain that evening. Everything turns to slush and mud. Repeat in a couple of days. That is the joy of living in the Midwest.