The Mindy Kaling Awesome Guy Challenge: Shoes

As I mentioned in my last post, over the next little while I’ll be undertaking the Mindy Kaling Awesome Guy Challenge, based on the 12 guy-improvement tips she offers in her latest book, “Is Everyone Hanging Out Without Me? (And Other Concerns).”

Reasons why I am doing this:

  1. For fun.
  2. The alternative is not doing it, which is decidedly less fun.
  3. Mindy Kaling is smart, funny, and perceptive, important qualities in the kind of woman I’d like to attract. I trust her observations.
  4. I’m far too lazy to come up with my own list, and it would be nowhere near as specific as hers.
  5. None of the tips include, “Don’t blog about trying to follow these tips.”

I’ll be doing these out of order. Let’s start from the bottom up, appearance wise, and go with shoes first.

Tip No. 10: I really think guys only need two pairs of shoes.

“A nice pair of black shoes and a pair of Chuck Taylors. The key, of course, is that you need to replace your Chuck Taylors every single year. You cannot be lax about this. Those shoes start to stink like hell. They cost forty dollars. You can afford a new pair every year. And if you can’t, why can’t you? You have much bigger problems. Stop reading this and go deal with them.”

I’m in a rare shoes-wearing period of not owning Chuck Taylors. For reference, they look like this:

I’ve been a Converse sneaker loyalist for years now. I’ve worn my way through a lot of pairs of Chucks, which routinely end up tearing in that weird way beside the toes just as winter is approaching. Sometimes I get bored of Chucks and go with another Converse model if it isn’t overly offensive (that popped-collar model they put out last spring is ghastly). I’ve been wearing this pair for the past couple of months:

I also have a pair of black dress shoes that I’ve polished up all nice for this photo:

I generally lack a reason to wear these, though I’ll usually put them on if I know I’m going out dancing. I’m in awe of the elaborate dress footwear on some of the businessmen I see downtown. Some of those guys turn shoe upkeep into a religion. My own closet is definitely shoe-tree-free. Back when I worked in an office I wore a pair of brown dress shoes that I kept on site to change into. I don’t own a car and rarely take any kind of transportation, so my shoe choices usually revolve around all the walking I do. And running and hiking, sometimes, which necessitate the other two pairs of shoes that I own:

I throw up in my mouth a little at the sight of Nikes in my closet, but they’re super comfortable.

So I’m at four pairs of shoes, two of which more or less conform to Kaling’s advice, depending on my mood. I think what deserves particular attention in this tip is her observation that if a guy can’t afford $40 a year for shoes, he has bigger problems. I buy a new pair of shoes at least yearly, but to be fair, Chucks are at least $60 in Canada if you get them at Foot Locker. It’s not that much more, but the idea seems to be that a guy needs dough in his pocket before he can enter awesome territory.

Fair enough. Most of this list is about getting one’s shit together, and if it requires finding common ground with good ol’ capitalism’s authority over proper shit presentation, so be it. I have a bit of capital.

I may add a pair of boots, however. Vancouver is a wet city, and I need something to combat the drifts back east. Maybe all the awesome guys are living in far more temperate climates.

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About Joel Crary

Joel Crary is a 30'ish 21st century writer living in Vancouver, British Columbia. He enjoys films, mostly. View all posts by Joel Crary

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