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