Simon Cowell

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‘Dear boys, dress like this’ meme roasts hilariously bad outfits

Simon Cowell really stepped in it with those boots.


Jay Hathaway

Internet Culture

Posted on Mar 1, 2018   Updated on May 21, 2021, 11:07 pm CDT

Back in 2014, a tweet offering (questionable) fashion advice for men spread through Twitter’s cluster of wildly popular “relatable girl” accounts—”Dear Boys, dress like this,” it implored. Here’s the original tweet, before it was recycled by accounts with millions of followers:

Jokes about this actual outfit aside, men clearly need help dressing. It’s 2018, and most of us still need to get our clothes game together. In the year of the Queer Eye reboot, “Dear boys, dress like this” has become a full-fledged meme. It’s mostly absurd and jokey, though. Thanks, internet!

The meme seemed to have kicked off on Feb. 27, with these tweets starring Simon Cowell:

The replies dissected Cowell’s outfit, clocking him for his pointy-toed boots that disappear into his too-long boot cut jeans. But then something really funny started to happen: people just replaced him with their own ideal male fashion plates.

These Twitter caption memes are pretty common: “dress like this” is basically another version of the Cleopatra meme or “this the ideal male body.” Specific versions of the meme come and go, but they’re perennially popular because the game is easy for anyone to play. All you have to do is pick a ridiculous image that fits the theme–it’s the social media version of Mad Libs.

But why is this the moment for “dress like this?” These memes don’t always need a news peg or a timely reference. It looks like the Cowell outfit was just that bad. U.K. Twitter had a field day with it, and it quickly expanded into the U.S.

Simon’s done us all a service, though. Now we have hundreds of tweets worth of advice on how not to dress.

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*First Published: Mar 1, 2018, 5:24 pm CST