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.

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 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.


22 Comments on "My Kinda Clothes: Southern Trad In Chicago"

  1. That last sentence says it all. Perfectly sums up my love for thirft shopping (electronically, mostly). I also have a Fair Isle sweater from Bank’s, good quality.

  2. Carmelo Pugliatti | December 9, 2016 at 1:50 pm |

    In old times 1930-1966,which were the finest clothing stores in Chicago?
    And about clothesm this city was “ivy” ?

  3. I think Chicago was more known for standard American style, or what Bruce Boyer calls the “midwestern grain salesman” look.

  4. Charlottesville | December 9, 2016 at 4:45 pm |

    Love the Southern trads. The gray flannels, argyle socks and penny loafers are absolutely perfect. Looking forward to a cold (but not Chicago-cold) weekend in front of the fire down here in Virginia, and flannels and loafers are just the thing.

  5. Front Porch Life | December 9, 2016 at 5:39 pm |

    I am located in St Paul, MN, unfortunately far away from the heart of Ivy Style. I have had some great thrift store finds for vintage clothing but it is very unlikely that I will score any classic Ivy garments. Folks like me seem to be limited to eBay for finding the true Ivy sport coats.

  6. Carmelo, there was a store called “Capper and Capper” that sold trad, gentlemanly goods from 1893 to 1990. I know because I bought an old Polo Coat of theirs and looked them up having never heard of them.

  7. Christian I would have thought the same but this Polo coat is full of the standard Ivy details. Unless Polo coats became very generally American in style at one point.

  8. Michael Brady | December 9, 2016 at 8:35 pm |

    I agree with Christian’s comment that Chicago was not known for adherence to standards of Ivy or traditional taste. A few small stores in the suburbs and the mainstay, Brooks Bros. constituted what there was of the East Coast influence. In the 70-80’s there was a surge of “jivey ivy” retailing centered around the influence of Ralph Lauren on traditional apparel.

  9. Michael Brady | December 9, 2016 at 9:53 pm |

    Capper & Capper was the the premier store of a group of men’s stores owned by Hart, Shaffner, & Marx. The broader-base stores were Baskins; all in Chicago. My father shopped at Capper & Capper. I would not call it traditional in the sense we speak of it here. It was certainly a fine store, but more geared to the customer who though Hickey-Freeman was the pinnacle good taste and fine make.

  10. Having traveled throughout the Midwest or South, I’ve never had a problem finding good men’s shops. Just ask the first person you see attired like you.

  11. PANI
    Thanks for the article. I’ll assume those loafers are ColeHaan.

  12. Christian, I bought a Polo coat that was made by Capper and Capper. It has lapped seams, swelled edges, patch pockets, half belt in back, sleeve cuffs and, of course, peak lapels. 100$ on eBay, fairly good deal for what would be a 1000$ coat.

  13. Waxed Cotton | December 10, 2016 at 3:09 pm |

    Some REALLY great looks here! The Crownwear coat can, in many instances, come off as Ivy “cosplay” but it looks very natural on you.

    Well done!

  14. Thanks everyone. If I may chime in on Chicago style, I only recently moved here but my impression of the style is very working class. Certainly there are business formal people in abundance, but overall it very much has a workwear, denim, sheerling, sort of feel.

  15. Carmelo Pugliatti | December 10, 2016 at 9:23 pm |

    In the perspective of European pop culture Chicago is forever linked with the sartorial bespoke glory of Al Capone (that for a criminal was a very well dressed man).

  16. Upcountry Tweed | December 11, 2016 at 12:18 pm |

    Non-OCBD under Crayola Crewneck? This is about as Ivy as a 1981 Trans Am on cement blocks in front of the trailer park. What next, Ivy yard art? Preppy spoilers for the Mustang? As far as Chicago is concerned, it’s an unwashed armpit of tackiness until you reach the depths of Lake Forest.

  17. Upcountry Tweed | December 15, 2016 at 12:30 am |

    No, the shirt in the second photo is NOT OCBD. 100% cotton OCBD collars should be visibly amorphous. This is much too stiff, much to neat to be a gentleman’s collar. The perfect analogy is an overly-clean car; an almost infallible sign that the driver is more into football and sitcoms than tennis and stocks.

  18. @Upcountry

    Enjoying your commentary. Would you care to submit an essay for the site? I’m thinking something along the lines of “The Right Kind Of People.”

    BTW, not kidding. Email me if you’re game.


  19. Upcountry Tweed, not only is it OCBD, it’s also Brooks Brothers. 🙂

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