How does this shirt look on this man?

This is Gene Weingarten of the Washington Post. He is a features and humor writer, and the winner of two Pulitzer Prizes. I am a devotee of his monthly live chat on, which is called “Chatological Humor.”

He recently bought this shirt:



The question, which Gene asked in his most recent chat, is: Does this shirt look good on him? He polled readers (see the top of the chat page for the polls and results).

So, does it? Why or why not? I am interested to hear the response of the Whatsiterati.


16 responses to “How does this shirt look on this man?”

  1. Dave says:

    Is this a trap? I don’t know. I think it looks okay, but not great. It’s a little too tight around the middle, so it ends up looking just a little small on him. Also, the stripes create a bit of a contour map of Weingarten’s middle-aged torso. Which, you know, we all end up there eventually, so it’s not really anything to worry about; it’s a matter of how willing the wearer is to show off his body.

  2. farrell fawcett says:

    Oh man, I love this stuff. I agree with Dave, the shirt is fine. Middle aged body not withstanding. The big problem here is definitely not the shirt. Why doesn’t he get a decent hair cut? Easy improvement. And the moustache. Ikes. Is that a signature moustache that is linked in some way to his radio personality/celebrity status? Otherwise, trim that thing. And a new pair of frames for his glasses? Oh, and is that his best pair of jeans? They’re looking a bit 90’s baggy and 90’s color. Very easy to remedy. Man, that’s fun. I really want to see the AFTER photo in a few weeks.

  3. FPS says:

    I could not agree more with Mr. Fawcett about the hair and moustache. The shirt is pretty neutral. Maybe looks a little young for him but no big thing. The haircut is just not flattering.

  4. swells says:

    My first response was “ugh,” but then I studied the issue to get to the heart of it, and for me, the shirt actually does look good on him. It’s just that it’s an ugly shirt. But I think, and I say this never having seen him before and just trying to imagine what he might normally wear–i.e. something shapeless, based on his pant selection–that it’s kind of flattering on him. Plus, I love him for posting this photo and asking his readers, so maybe that’s making me feel generous despite his poor selection.

  5. Dave says:

    Yeah, maybe keep the shirt, change everything else. But then he’d be a different person.

  6. FPS says:

    5: “Az der bubbe vot gehat baytzim vot zie geven mein zayde.” (The sanitized version of this Yiddish saying is “if my grandmother had wheels, she’d be a wagon.”)

  7. LP says:

    If you click through to the polls, you’ll see that around 75% of both male and female respondents say the shirt either “doesn’t look so great” or is “ridiculously bad.” I also voted that I thought the shirt “doesn’t look so great.” It seems ill-fitting, too tight around the middle.

    What was interesting were the reasons people gave for why the shirt looked bad. Among the choices of “nothing’s wrong,” “not appropriate for your body type,” “not age-appropriate,” “doesn’t fit” and “bad color,” more people chose “not age-appropriate” than anything else. I found this surprising – really, this was a style that an adult can’t wear?

    But now that I consider your comments, I think the problem is that it looks so much younger than every other part of Weingarten. The problem is not that the shirt skews young, per se. The problem is that Weingarten’s hair, glasses, mustache and pants skew older. So the whole package is rather … confusing.

    What I’d really like to see is the Weingarten full makeover, where he dresses and grooms himself to suit that tight little striped number.

  8. FPS says:

    You can only make the most of what you’ve got. I used to dream of having fine, floppy hair to hang down my forehead like Rupert Graves in A Room with a View, but at some point I had one of those realizations of something you knew but hadn’t admitted to full consciousness: I would never have floppy hair, and it wouldn’t go with my face anyway. I’m not sure exactly what Gene Weingarten wants to look like, but if he’s asking me, a buzz cut would be a great start toward making the most of what he’s got. And either a shave or a beard.

    Hi, I’m in over-commenting mode.

  9. Gene Weingarten says:

    Thank you all. I started growing that hideous mustache AT Woodstock. It’s going to remain where it is until I die, or chemotherapy takes it.

    Other than that, there ain’t much I can do. Tragically, this is what I look like.

    Chicks dick me, though. It’s the hair.

  10. Gene Weingarten says:


  11. LP says:

    Gene! Welcome! We do sock-puppet a fair amount around here, so I want to just let the Whatsiterati know that this is indeed the great Gene Weingarten. You can tell by his horrendously inappropriate faux pas in comment 9, and the panicked response that follows.

    Okay, so the mustache stays. But what about the rest of the makeover? Any chance? One reader suggested a buzz cut. It could work.

  12. LP says:

    PS: Because we did pile on your look, and because you are a good sport for joining in, I wish to reiterate for the masses that you can wear whatever you want as long as you continue to write the way you do. Seriously, people, Gene is the man. If you have not read his profile of The Great Zucchini, please do so here.

  13. I feel a teeny bit like I’m in one of those Mean Girls three-way calls where it turns out the other girl was on the line the whole time.

  14. swells says:

    If I thought I loved him for posting such an enjoyable question, I now love him ten times more for commenting on our humble blog. And I’d like to reiterate that it’s just the shirt that’s bad.

  15. Tim says:

    Gene Weingarten, you are a brave man indeed, willingly subjecting yourself to the critique of your readers (and the Interwaffle in general) in this manner. All the same, I’d say you need to lose the shirt. To me, it doesn’t shout out, “I’m a two-time Pulitzer winner,” as much as it admits, “My kids think I need to start dressing a little more ‘street’.” You’re beautiful just the way you are.

  16. PB says:

    I am always mystified by this notion of age appropriateness in clothing. Is it the inevitable changes in the body that dictate the shift? Is it the bias toward the styles of our youth which eventually look out of date? Or that are so old we really don’t give a shit? Or is there a magic system of fashion that truly dictates age lines like the equivalent of white shoes after labor day? I am always confused.

    This by a woman whose favorite t-shirt is adorned with intergallactic kittens shooting lasers from their eyes worn with a faded pair of jeans and felt clogs. I only occasionally have a mustache however.