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Endless Thread

Derek 'The Menswear Guy' Guy

Endless Thread

WBUR

Reddit, Technology

4.22.7K Ratings

🗓️ 6 June 2025

⏱️ 40 minutes

🧾️ Download transcript

Summary

Men's fashion might seem like a niche topic. But people of all genders and sartorial sensibilities follow Derek Guy on X for his clothing takes... even if they're not quite sure how they found his page.

Endless Thread talks to Derek about how he weaves together humor, history, cultural criticism, and political commentary to make fashion feel relevant to people who have never seriously considered it before.

Show notes

Credits: This episode was produced by Ben Brock Johnson and Amory Sivertson. Production assistance from Grace Tatter. Mix and sound design by Paul Vaitkus. It was co-hosted by Ben Brock Johnson and Amory Sivertson.

Transcript

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0:00.0

Support for this podcast comes from Is Business Broken, a podcast from B.U.

0:04.9

Questrum School of Business. What is short-termism? Is it a buzzword or something that really impacts businesses in the economy?

0:13.2

Stick around until the end of this podcast for a preview of a recent episode.

0:19.2

WBUR Podcasts, Boston.

0:25.5

Derek, do you remember if there was a particular moment in time that you realized that you

0:32.4

had an eye for style or fashion or however you think of it.

0:38.2

Like, do you remember how old you were and what you were seeing?

0:42.3

No, there was not a Tom Ford moment where I thought, I have sophisticated taste.

0:48.3

No.

0:48.9

You took one strap of your Ashkosh-Bogash off and let it down, and then you knew.

0:55.8

That's when you knew.

0:58.5

Derek Guy, the menswear guy, doesn't really know how it started.

1:04.1

It seems to have started on various internet forums devoted to discussions of fashion and style.

1:10.1

How's it going?

1:11.6

Well, you don't have to look far on Reddit or Twitter to find discussions around fashion that discuss or are driven by Derek.

1:19.9

And maybe that's because he's pithy and snarky and extremely online whilst discussing highfalutin topics with some balance.

1:31.8

So there are some people who think that there is some objective truth in fashion, that this

1:36.7

is a better look and that's a bad look. And there are some people who view it as completely

1:41.2

subjective that, you know, well, I just put on whatever makes me feel good

1:44.9

or what I think looks good and everything's legitimate. Everything that anyone chooses is totally

1:49.3

fine. Oh, thank goodness. We're all our own special mannequin. But you best come correct,

1:55.4

mannequins, and be thoughtful in your presentation. I think of dress as a kind of cultural language, and just as we use

...

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