My Kinda Clothes: Southern Trad In Chicago

“My kinda clothes” is a charming little phrase coined by Charlie Davidson of The Andover Shop. Here at Ivy Style, it’s a regular series in which readers share their favorite clothing items. If you’d like to share yours, use the contact button above.

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I picked up my style of dress largely without knowing what it was. I recall my paternal grandfather often in khaki shorts, tucked-in OCBD shirt, white socks and loafers. He was a respected member of local society in Mexico, and there was much about him I wanted to emulate as a young man. Much of my early wardrobe staples came directly from what I observed from him.

I attended a Southern US college and discovered two things that greatly influenced me. First, the way my grandfather dressed was something called “trad.” Second, there was a Southern variant. I incorporated the Southern love of pastels and propensity for wild display of team colors (Go Cards!). Consequently, I oscillate between the subdued, restrained, trad of my grandfather that usually finds its way onto my person in the colder months, and the bright, snotty, FU trad that makes up my summer wardrobe. Winter being upon us, and being a denizen of a currently very chilly Chicago, I shall focus here on the coverings and layers that make up my winter wardrobe.

Ivy Caps
I have a strictly practical relationship with hats. I loathe affectation and wear a hat only when it has a practical purpose, like keeping my head warm or shielding it from the sun. Fall and winter sees me in Ivy caps when outdoors. These hats come to me from my grandfather, who appreciated their relaxed and approachable style. I prefer a Brooks Brothers or Stetson tweed, but a cheap Sears cap with ear flaps doggedly fights its way to the top of my rotation in the cold Chicago winters.

OCBD Shirts
My shirts are likely the most uniform item in my wardrobe. Five days out of the week I can be seen in a light blue oxford-cotton buttondown. The sixth day might see a white OCBD. And on the seventh day god created the white crewneck t-shirt, and I wear it without any sense of shame. Brooks Brothers supplied my oxford shirts early on but I, like many, gradually shuffled off the non-iron monstrosities that consumed most of their shelf space before someone got the grand idea to bring back the classic shirt. In the interim I came to be a fan of Kamakura (who now makes up the majority of my OCBDs) and Canadian company Spier & Mackay. The Kamakura collar roll is, by now, legendary, but the Spier & Mackay collar is not far behind. Incidentally, they do custom shirts as well, so if you want more or less collar roll they can accommodate.

Grey Flannel Trousers
Like light blue OCBDs, grey flannel trousers are a wardrobe staple for me, and consequently see a lot of hard use. I will wear them with nearly everything: navy blazer, tweed sportcoat, roll-collar sweater — perhaps not the crewneck white t-shirt though. Howard Yount provided some of my earliest grey flannels, worn constantly through the avenues of the University of Louisville. Lands’ End provides the inexpensive, durable-as-heck flannels I wear to play catch with the dogs. I have recently begun to experiment with custom clothier Luxire, whose selection of trouser fabrics is well known. Not only that, but I can get any configuration I want. High-waisted trousers? Not a problem. Two inch cuffs? You got it. Monogram on the belt loops? Of course not, who would do something that gauche?

Fair Isle or School Sweater
To be sure, I adhere to that old Brummellian adage that if one is noticed for his clothes he has failed. Nonetheless, every time I wear a Fair Isle sweater I get a comment or two on it. This I am willing to put up with because Fair Isle sweaters are so spectacular. This touch of Commonwealth flair speaks to the Anglophile in me and would have been appreciated by my grandfather. I will wear them with nearly anything in winter. Tweed sportcoats are a perfect match, of course. A navy flannel blazer wouldn’t turn its nose up at one. My favorite, however, is to wear them with a shooting vest or hunting jacket. This rustic country combo is perfect for strolls outdoors with the dogs, or a glass of bourbon at your neighborhood pub (3 drops of water, no ice, please). I prefer the real deal, woven in the Shetlands, and my favorites are from Jamieson’s of Shetland. That said, I have several cheaper facsimiles from Jos. A. Bank that get the job done. If you can get the J.A.B. sweaters at a discount they are a fine value, otherwise, spend a tad more and get Jamieson’s. On game day only school colors will do, so I switch to one of several school sweaters, my favorite of which comes from Hillflint. Taking their stylistic queues from the heyday of the Ivy look, they are a godsend in a world oversaturated with athleisure wear.

Galoshes
The winters in Chicago are brutal on humans and shoes alike. Chicago is a walking city, so shoes take a beating no matter what time of year it is. But in the winter the snow, ice, road salt, and gravel can all conspire to destroy your shoes if you aren’t careful. I have never been one to baby anything I wear, but shoes sometimes need a little extra protection. Swims brand galoshes perform marvelously for this purpose. They come in an eclectic array of colors, but a simple brown draws little attention and blends in well with most my of shoes (I rarely wear black shoes). The beauty of Swims is that the interior has a velvety soft lining which will not rub off the wax on your shoes. On particularly icy days, Yak Trax may be added to prevent embarrassing Gerald Ford impersonations.

Overcoats
Overcoats are an area of some importance in Chicago. I like to go vintage or legacy brand here, mostly because the overcoats available from fashion brands are usually too short to be effective in cold weather. Below the knee is the minimum for a business formal overcoat, mid-calf preferred. Casual coats I don’t mind going a little shorter on. Ralph Lauren’s Columbia cashmere overcoat gets the job done for business formal attire. For casual days I will usually reach for a vintage Crownwear overcoat, pictured here, which I obtained for a song on eBay. The great thing about loving vintage clothes (frugality being my watchword) is not having to pay a fortune for high-quality garments. — PANI M.