There’s a hole in my shoe. Not in the sole, either, though that’s its own nightmare – you’re walking through a downpour in NYC in shiny dress shoes and suddenly one foot is sump-pumping in rainwater like it’s trying to dry out the city. (Though in fairness, also very hobo-chic, holes in shoe soles.)

This hole, the one I have right now, is on the top of my shoe. I don’t see many holes on the tops of shoes, but it has happened to me before. Which begs the question, is this normal? Is my big toe just so jacked that it’s literally exploding out the roof, like a dancer bursting out the top of a novelty birthday cake? Are my toes naturally curled upwards, like those Arabian slippers with the loopy tips?

I’ve lived with this hole in my shoe (see photo above) for about a week now. That’s because there’s no exact moment a hole appears. With shoes, it just sort of gradually wears and tears, the way that a slight concave forms on the long marble steps of the Acropolis, and one day you’re looking down and boom – your sock is looking back at you through this little skylight.

Here’s what I’ve discovered in the last week:

You walk around with a hole in your shoe, it’s the kind of thing people notice. It’s not like torn jeans. People buy jeans that are already torn. Try explaining that to people unfamiliar with modern fashion. I had that experience when I was living in Nepal – I was wearing a pair of J. Crew cargo shorts that were ragged at the hem. The kids pointed it out immediately.

“Brother, you use scissors? You try make half pants?”

“I didn’t do it myself. They come like this. You buy them.”

“You no buy them like that brother. You are joking I think.”

“I’m not joking. This is American style. American style shorts.”

“[Frowning in confusion]……Why you break your pants, brother?”

“I didn’t break them. They’re frayed. I want them like this. I paid money and chose shorts that were frayed like this.”

The kids literally didn’t believe me. They thought I was just really bad at making half pants. Have some self-respect, they were probably all thinking in Nepalese. And I’ll bet in Nepalese it sounds way worse and more humiliating.

So I’m looking down at this hole in my shoe and wondering if this, right here, is why men get married. I mean, yes, I know, we are called into a covenant relationship and there’s the necessity of procreation and whatever, but how often are men changing their sheets if they’re not married? How long will they wear that dress shirt, holes in the armpits and collar button dangling from a single thread like a climber who’s lost his purchase on El Capitan?

Early in my own marriage, when Liz suggested that she get me some new clothes, I first insisted that I needed nothing. She then rephrased it to make it sound like I was doing her a favor. Graciously, I agreed.

Now, not having any experience with marriage, I assumed my wife would look at what I had in my closet and simply buy updated, un-torn models of those clothes.

Liz did not do that.

Instead, my wife bought cool, stylish sneakers, ones that were not running shoes. She bought me jeans by designers I didn’t recognize, ones that had to be tailored. She bought me fitted shirts that didn’t billow like a spinnaker in a typhoon.

They looked….well, I guess they actually looked pretty good.

The problem was that it took me forever to wear them in public.

Here’s the issue:

I don’t know if this is common to other men, or if this divides the genders, but for me, I have a general fear of wearing new things. Trying new styles. Getting a different haircut.

My fear comes from the notion that my friends will look at me with skeptically raised eyebrows and ask, with a chuckle, if I am joining a boy band. (Do they still make those? Boy bands?) Even just a new shirt, I somehow have this fear of people pointing out that I have a new shirt.

Is that weird? It’s weird, right?

I think it’s rooted in the image I have of myself as somebody that just doesn’t really give much thought to my appearance. That I’m more concerned with Important Things. Or that I don’t need that kind of affirmation from the world.

In my twisted pattern of anxieties, wearing a new shirt undermines that image. It makes me anxious when I wear something new out of the house.

It’s amazing how much power I give others over how I feel about myself.

So here’s how, at the tender age of 43, I have learned to cope with that particular anxiety.

My mantra, every time my wife gets me new clothes, is this: I have an Audience of One.

If my wife thinks I look good, then I look good. People ask why I was growing my hair long. I told them, truthfully, that my wife suggested it. When they asked why I cut it a year later, I told them because Liz said she thought it would be cool for me to try short hair again.

I have an Audience of One.

If I look good for my wife, I look good. I don’t need to look good for anyone else. I need to dress respectably for work, I suppose, but she won’t let me walk out looking like an idiot. She’s good like that.

Lizzie has given me a few days with this hole in my shoe thing. But I can see her eyeing it. So I’m off to get new shoes, myself, for maybe the first time in twelve years. I think she’ll be proud.

And speaking of clothes that hung on too long, here are…

The Top Five Clothes I Couldn’t Quit:

  1. Nepal Fleece.

I had a fleece, so warm, so thick, that was my favorite thing in the Nepal winters. It had a burn hole in the wrist area from an open fire, it was trampled underfoot and used as a pillow for months on end. It was, if we’re being frank here, repeatedly infused with the pee of very young children. And still it hangs in my closet in America. By all rights this thing never should have been allowed through US Customs. (They’re worried about bringing in pineapples but not this?)

  1. Flip-flops.

I don’t know if they make flip-flops out of recycled razor blades or what but I can’t wear them. They slice up my feet like shoe-blenders. Also I look terrible in flip-flops – my legs and feet are so pale that I look like I’m tottering around on thick Glo-sticks. So when I found a comfortable pair I never took them off. I spilled paint on them one time and Liz thought that was the moment but I held on to them like a baby with a pacifier.

  1. College Hat.

Back at UVA I had a Virginia hat that I wore until it was practically a living thing. The problem was that there was no realistic possibility of waking up more than 10 minutes before the start of class, let alone taking a morning shower, and thus this hat became a kind of containment system for a desperately greasy head of hair, morning after sad, rushed morning. (College was fun. And gross.)

  1. Any and All Jeans.

I have pairs of jeans that are so torn they hardly resemble pants. They look like something you’d see in a cubist exhibit in the MOMA. I always feel like I’ll need them at some point. I use one pair when I’m painting, but the rest are just sitting there like the last man on the bench on the Golden State Warriors, secretly hoping the team bus hits a patch of black ice in Minneapolis.

  1. Single Socks.

I can’t think of a more manifested sign of pure optimism than the length of time I hold on to single socks. Years. It just feels like the moment I throw away a single sock the other one will pop out of the laundry room from behind the door and be like “Surprise!” and then it’ll look sad and say “Oh, sorry, I thought you were the other sock” and then will go back to awaiting a reunification that will NEVER HAPPEN.

Okay. Shoe time.

By | 2018-08-08T08:36:49-04:00 August 8th, 2018|14 Comments


  1. Elsa August 8, 2018 at 9:02 am - Reply

    The Best!

    • Conor August 8, 2018 at 9:46 am - Reply

      This is why I am obsessed with your fashion people watching in NYC. It’s like another planet!

      • Liz August 8, 2018 at 3:48 pm - Reply

        Yes, Elsa, we need a coffee table book!!

        • Conor August 8, 2018 at 4:03 pm - Reply

          I’m totally starting the rumor that Elsa is publishing a coffee table book. Starting now.

  2. Rachel August 9, 2018 at 3:16 am - Reply

    You do realize that you have inherited this hang-on-to -clothes-in-shreds thing and leave-new-clothes-in-the-closet-for-months-before-wearing thing from your dad, right?

    • Conor August 9, 2018 at 9:05 am - Reply

      One of many dubiously wonderful qualities, clearly….

  3. Joan August 9, 2018 at 3:55 am - Reply

    Right on,Rachel. Of course, all our strange habits are inherited and Conor is no exception. I fear the sock thing started early and who can just discard beloved jeans. Bury them lovingly in the back of the closet.

    • Conor August 9, 2018 at 9:05 am - Reply

      I think I’m going to have to watch Finn closely. He’s got our DNA running through him.

  4. Amy Krahn August 9, 2018 at 9:45 am - Reply

    If you’re going to publish a book, it should be Conor Grennan’s Book of Lists. Only it should be titled “Connor Brennan’s Book of Lists”. Obviously.

    • Conor August 9, 2018 at 10:15 am - Reply

      It’s got a nice ring to it! (Also it gives me hives, but hives with a nice ring to it!)

  5. Steve Sheets August 9, 2018 at 2:23 pm - Reply

    There’s a hole in my shoe, dear Liz-a, dear Liz-a…

    • Conor August 10, 2018 at 11:40 am - Reply

      You would fit perfectly into the Grennan house. This is what we do. There is a song for everything, all the time.

  6. Dad August 20, 2018 at 11:01 am - Reply

    Oh dear me dear–dad-worthy or not–how does it feel to belong to a club your Da belonged to and continues as a full-time unpaid- up (of course) member of?? There y’are.

    • Conor August 20, 2018 at 1:08 pm - Reply

      It is not the fanciest of clubs. But that wouldn’t really be our style….

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