Twenty-six years ago when I graduated OPRF, for the graduation ceremony they required a dark suit, white shirt, and red tie for the boys and white dresses for the girls. The absurd and offensive symbolism of both of those moves aside, this meant I had to get a suit. I had jackets and ties, which I like, but I owned no suit because both then and now I like style but dislike uniforms. 

But get a suit I did: medium grey, light pinstripe, and cheap as possible without buying it out of the trunk of a car. It came out occasionally in the years thereafter, mostly at Halloween, and was eventually wholly lost to the mists of time. I hope whoever found it at Goodwill got some use out of it, maybe as a dishrag or a costume for a dog.  

As the four-year contract that is my day job hits the three-quarter mark, I’ve started to think about what I’m going to do next. It’s been a while since I job-hunted in earnest, and I’ve spent some of that interim time doing stuff like learning to eat and exercise like an adult and getting in better shape and watching my beard turn gray and moving firmly into the mid-career phase of life. I am now too old to think of other people as “grownups,” plus I don’t particularly like working, but I enjoy money, plus my old suit and three sport coats no longer fit, so: It is time to buy some suits.  

Generally I dislike buying new clothes. I’ve never understood why clothes cost what some of them do, the return on my investment for dressing up is generally low — lot of backhanded, passive-aggressive comments like “You clean up nice!” — and, with the sole exception of David Letterman, I never knew anyone who both enjoyed wearing a suit and was a force for good in my life.

The problem with this need is that it has been 26 years since I bought a suit, and the Sears on North Avenue has closed. (Sidebar: What are they going to do with that space? There aren’t nearly enough windows for lofts and you can’t put a Whole Foods or a Mariano’s in without a gut-rehab level modification, plus no corporation in their collective right mind is building something that size in Chicago when they could play the three villages across the street against one another in a tax-credit bonanza. Good luck, y’all.) Without that Sears, I’ve lost my suit-buying north star, my fallback fail-safe. 

I am assured by reputable sources (Google) that there are really only two color choices for the interview suit of an adult: blue and dark gray. This is garbage for several reasons. One is that two prime choices is a holdover from the days when sallow Europeans declared everything they had the Permanent World Standard of Good Taste — which I resent on behalf of a solid 75 percent of the rest of the world — and two, neither of those is a good color for me. Light colors look good on me. Dark colors, save black, do not. I made a few inquiries and it turns out the darkest gray is black to everyone in America who isn’t a suit salesman, so we’ve escaped disaster there. 

Still, why aren’t teal and purple and canary yellow the best colors for a suit? I look good in those colors, even if I also look like I have an unhealthy fandom relationship with Prince or maybe Dick Tracy. I look great in houndstooth, brown corduroy, black leather, and white linen. All good for jackets, all bad for suits. I could pull off colors. But alas, a bunch of pasty people who never saw the sun picked the “classiest” colors 400 years ago so now I have to drop a bunch of money on either a suit that looks like a sad cloud or a suit that’s an emblem away from a prep school uniform.

Anyhow, I’m going to look at suits this week, so assume you’ll hear more about this next month. Have a kind thought for the person of sales who has to field my questions. She’s going to need all the love and support she can get.