I faced a shoe-choice dilemma the other day that I thought I would share, which, although not a perfect parallel to exigent’s tale posted in the dressing section, has instructive value. I was attending a 25th wedding anniversary. All I knew was that the event was being held in a restaurant, and given the hosts, was likely to include a wide range of people of many backgrounds and ages. I had a limited ability to change from what I was wearing during the day, which meant all I could do was jettison a bright checked shirt and wool tie for a french cuffed solid shirt and smooth silk tie. That left me in heavy wool flannels and a navy serge DB blazer. The question was shoes. Looking at my trousers, I reached for a pair of black chukka boots with dainite soles. I pulled back my hand. This was an evening celebration for people I liked and no compromises would do - I switched to a pair of black medallion wholecuts, for an altogether more polished look. This was not a formal event (in the non-rules sense) and the chukkas would have looked fine, particularly with the textured trousers. But they did not convey the mood of what I considered to be both an important and joyful occasion. As it turned out, there was dancing, so I was particularly glad for the right shoes.
Now, for the interesting part. I couldn’t help myself from doing a survey of the room. First - the couple’s sons and their college-age and postgrad friends were all in the ubiquitous wide square-toed monstrosities. The people I knew to be ex-diplomats, plutocrats or investment bankers were in black cap-toes or similar. The hedge-fund guys were in expensive business casual and everyone else (the majority) was in everything else. My favorite, though, was an elderly uncle of the “bride“ who was turned out splendidly in his version of casual - nice light flannel trousers, camel-colored ventless “blazer” with smooth metal buttons (only one on the sleeve), a nice shirt worn over a “dickie” or mock turtleneck and the most beautiful honey-colored derbies. They had a 360 degree welt and I thought they might be Alden’s Whiskey Cordovans.
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