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derek guy@dieworkwear · Sep 24, 2026

I was tagged in this but it appears we have each other mutually blocked. You will never escape this stupid cycle if…

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Summary

Men's fashion style shouldn't be reduced to memorizable trend-based rules that constantly change. Instead, approach style as a visual language rooted in cultural history and aesthetic references, which remain timeless and help you develop coherent, individualized fashion sense rather than chasing fleeting trends.

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  1. #1

    I was tagged in this but it appears we have each other mutually blocked. You will never escape this stupid cycle if you distill men's style into a set of memorizable rules. "Wear slim pants." "Wear baggy pants." "Wear a henley." "Wear black with brown." 🧵

  2. #2

    If you approach style in this way, you will continually ping-pong between nonsensical outfits, each one rising and declining depending how many other dumb people adopt these maxims, resulting in distorted aesthetics. One year, it's slim fit; next year, it's baggy fit. On and on.

  3. #3

    Instead, you should think of style as a kind of visual language shaped by history. Whether you should wear slim or baggy pants depends entirely on your cultural references, which are fixed and unmoving.

  4. #4

    Here are tow men wearing dramatically different pants silhouettes (scroll through all the photos to see the modern and historical references). They will always look good because the outfit is anchored by cultural history.

  5. #5

    We can do the same for even baggier pant silhouettes. For me, this aesthetic will never go out of style because it's not about trends. It's rooted in something that has and will always have cultural capital.

  6. #6

    Once you've chosen a certain aesthetic, there are ideas on how to communicate within that visual language, much like how I'm currently using English spelling and grammar rules right now to communicate certain ideas to you.

  7. #7

    Given those parameters, two men with similar height and weight may still need different types of pants to communicate the same silhouette ideas *within* that aesthetic. Justin Kwan explains this well in his video. IG justin__kwan

  8. #8

    Most people don't have a strong sense of aesthetics and they may be grasping for ideas on how to put an outfit together. Combined with the fact that we've moved away from books, magazines, and even blogs, and towards superficial communication mediums (such as tweets) ...

  9. #9

    ... this means that many people are left with memorizing very simple, stupid ideas online. "Men shouldn't wear backpacks." "Brown never goes with black." "Pants should be in so-and-so cut." The more you rely on these "rules," the more money you'll waste.

  10. #10

    Better to ditch this approach entirely and understand style in a more holistic sense. For more thoughts on how to develop good taste, you can read this article. dieworkwear.com/2022/08/26/how…