My Lack of Fashion Sense, but Do Guys Really Dress Like This?

I treat shopping for clothes the same way I treated art time in grade school; the goal was not quality, the goal was getting it over with as quickly as possible.

Clothes have never meant much to me. In an ideal world, I’d still be wearing the clothes I had in college, and the first suit I ever bought, from more than 35 years ago. And if I weren’t married, there’s probably a good chance I would be.

But I also admit that I used to get a little concerned when I would read the Saturday edition of the Wall Street Journal. In its Off Duty section there is usually an article or two about men’s fashion, and while reading such articles I am left wondering, “Is this how guys really dress?”

For example, take the picture at the top of this post. Here’s a description of the outfit:

The new roomier silhouette allows for more freedom of movement, as ably proved here by American Ballet Theatre dancer Grant DeLong. Dress Shirt, $395, Ermenegildo Zegna, 212-421-4488; Alexander Olch Couple Silk Noile Stripes Necktie, $150,; Wool Wide Trousers, $845, Paul Smith, 646-613-3060; Falke Milano Mid Calf Cotton Sock, $30, The Sock Hop, 212-625-3105; Leather Lace Up Dress Shoes, $1,250, Salvatore Ferragamo, 866-337-7242

When I total that all up, it comes to $2,670. And that doesn’t even include a jacket!

To get an idea of the cost of an outfit that includes a jacket, here’s another proposed ensemble:

The less-strict suit needn’t look like a costume from the film ‘Wall Street.’ This version has a casual, sporty feel. Caravan Jacket, $1,985, and Pants, $885, Marc Jacobs, 212-343-1490; Sweater, $250, A.P.C., 212-755-2523; Adidas Originals Stan Smith Shoes, $75,

Total cost: $3,195

Maybe this type of clothing lasts a long time, but I’m guessing the guys who dress like this like to buy new clothes as frequently as Taylor Swift changes her boyfriend.

I had no desire (or the money) to dress in the styles often shown in the pages of the Wall Street Journal or Esquire magazine. So that’s why I was thrilled when people like Mark Zuckerberg and Steve Jobs came along.

Mark Zuckerberg wears the same gray t-shirt every single day, offering the following reason why:

“And there’s actually a bunch of psychology theory that even making small decisions around what you wear, or what you eat for breakfast, or things like that, they kind of make you tired and consume your energy. And my view is, I’m in this really lucky position where I get to wake up every day and help serve more than a billion people. And I feel like I’m not doing my job if I spend any of my energy on things that are silly or frivolous about my life…”

The same article draws a comparison between Zuckerberg’s dressing habits and President Obama. In a 2012 interview in Vanity Fair, Obama explained his approach:

“You’ll see I wear only gray or blue suits,” he said. “I’m trying to pare down decisions. I don’t want to make decisions about what I’m eating or wearing. Because I have too many other decisions to make.”

And perhaps the first person that brought such an approach into vogue was Steve Jobs, who was famous for wearing his black mock turtlenecks, Levi’s, and New Balance sneakers everywhere he went.

Jobs claimed he did it for the convenience as well its ability to convey a signature style. His closet contained about 100 of the black turtlenecks!

There’s also the recent story of the Australian TV anchor who wore the same suit every day. My kind of guy!

So now I feel very comfortable with my two suits, a couple of dress shirts, and a couple of pairs of khakis, almost all bought from Kohl’s.

And I’m really looking forward to retirement, since I’ve already got my outfit planned. Shorts, t-shirts, and flip-flops, every day. Steve Jobs would have been proud.


14 thoughts on “My Lack of Fashion Sense, but Do Guys Really Dress Like This?

  1. But do you have a ballet move for that shorts-and-flipflops outfit? You’ll have to post a picture of that when you retire.

    As for me, I don’t fit the mold when it comes to “women and shopping.” I hate to shop and would dearly love to wear the same thing every day. Maybe not the exact same black shirt and jeans, but something close. I love color, so I might wear a different-colored T-shirt or turtle with my jeans. This is one of the rare times I agree with Zuckerberg.


    1. Hi Suzy,

      The ballet move is something I can work on when I retire. And I’ll admit to being a fan of Zuckerberg’s. My level of respect went way up when I saw him give an entire interview in China – in Chinese. Quite impressive.


  2. Great post Jim. I wear different outfits, but there’s no way I would ever pay the prices I see in style magazines. I can assure you that when you retire you’ll need 1/10 the clothes you have now–I’ve taken a carload to Goodwill already, because all I wear now is shorts and t-shirts. It’s amazing how little I need now.


  3. Thrift stores. I stroll through looking for old bedding for the dogs and make one run through the clothing…maybe. If a color catches my eye, especially in a jacket with pockets, and it’s the right size (and cheap!) I grab it


    1. Hi Mona,

      I am a fan of thrift shops as well. In fact, as I write this, I am wearing a Burberry suit that only cost me $150. I think the retail price was over $1,500.


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  5. The images don’t show but when I click on them, they do open in a new window. I’m beginning to think that it might be by design… One of the links in the text times out. (That’s just so you know if you wanted to edit the post. For SEO purposes. Or whatever. Feel free to delete this comment if you’d like.)

    I’m all about dressing clean. That’s the most important.


    1. when I switched from to, a lot of the links to the images got broken, and I update them sort of on demand. I have fixed this one as well. I appreciate you letting me know…

      dressing clean and comfortable is my approach…

      Liked by 1 person

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