Dress for the job you’re about to lose, not the job you’re never going to have

A fashion guide for men of advancing years who still drag their carcass to the office each day

My youth was full of unbridled enthusiasm and hope for my career. I thought I'd make Vice President someday, somewhere. Possibly Chairman of the Board. Alas, several corporate downsizings later, my career has taken a nose-dive second only to the nose-dive of my testosterone levels.

I’ve accepted as fact that the only company I'll ever lead is the LLC I'll create for driving Uber.

Meanwhile, come Monday morning, I'll be lucky to find a pair of stretch-waist trousers in my closet that aren't stained with mustard.

The advantage of being in the twilight of my business career is that my wardrobe is easier to manage than falling off of a bar stool. If there's no chance of advancement, then I may as well try to save money on clothing. It's all I have left, really, given that my 2% raise each year doesn't even cover the increase in medical bills I experience, now that I'm a man of advancing years.

Here is a guide on how to push the limits of the dress code at work once you realize it doesn’t matter what you wear. 


I haven't bought a new pair of pants in seven years. I caught a break when the local Montgomery Wards closed and I bought every single pair of 40×30 stretch-waist, khaki trousers on clearance.

When a pair of khakis has too many stains for even my low standards, I re-color them them to a new shade of brown. “Do you mean dye them?” you might ask. 

Nope. I re-color them with my own concoction that blends the stain with the fabric evenly. Here’s the recipe:

  • One part brown vinegar
  • One part brown shoe polish
  • Two parts vodka

In a large bowl, mix the vinegar, shoe polish and half the vodka. Drink the remaining vodka, then pour the mixture on your pants while wearing them and rub the crotch vigorously. Roll around in used kitty litter to remove excess moisture. 

And my survivors, should they claim my body, won't have to worry too much about which pair of brown pants to choose for my burial.


When I was younger, I favored broadcloth button-down oxfords. I got both kinds: white and blue. They were, technically, dress shirts. Given the size of my belly and man boobs, I'd have been better off wearing a dress. A maternity dress.

Pro tip: if your man boobs lactate like mine do, wear a sweater vest to hide the stains. 

Dress shirts require ironing, at least, or to be starched and pressed by a dry cleaners. That's time and money I can no longer afford. The only reason I'd wear a dress shirt now is for a jury trial. 

Instead, I wear collared sport shirts, like those intended for golf or tennis. Watch the obituaries for death notices of local businessmen, and buy every shirt of theirs available at the estate sale. The size doesn't matter because those shirts stretch like crazy.

I like the effect of too-tight sport shirts anyway because they roll up your arms into your arm pit, obscuring the sweat stains.  And you can almost convince yourself it's because your bicep is too massive for the sleeve.


For about a decade after college, I wore Johnston and Murphy wingtip oxfords. They weren't flashy shoes. They were sturdy and business-like, and that's the message I wanted to send: "I'm serious about my feet and also probably serious about my work."

My feet understood the lie, as my fallen arches, bunions, and ingrown toenails conspired to make wearing serious shoes impossible.

I got a note from my podiatrist that I needed to wear cheap shoes with velcro closures available at the dollar store on the corner. My boss was suspicious because the note didn't specify orthopedic shoes. Then I showed him my feet and he never wanted to be bothered again.

Bare feet bother people at the office, in general. Once I started clipping my toe nails there, no one ever questioned my footwear again.

Neck Ties

I have a couple of ties in the closet, somewhere. They're so old that they've gone out and back into style twice.

I only keep them because I have a persistent fantasy that a woman will enter my life who likes to tie me up with neck ties before having her way with me. Is that weird?

I don't think it's weird, either.


I wear some.

I used to make sure my T-shirts never had arm pit stains from deodorant. If a sock had a hole, I threw it away. I would wash my jockey shorts if they were soiled.

That was when I worried what medical personnel would think of me if I was in an accident.

Now I hope that they are so repulsed by my undergarments and general lack of hygiene that they withhold medical service and put me out of my misery.

Considering that my job doesn't include health insurance, it's a safe bet they'll get on board with it.


You leave this world with everything you brought into it, which is dirty hair and a smelly sheen on your skin.

In between, you wear clothing. We sometimes put a lot of time, effort and money into our wardrobe. But so does Ronald McDonald. And if he's not the poster boy for career stagnation, well then maybe you could hire me for that job instead.