Derek Guy

The tech hoodie was itself a uniform signaling 'I don't care'

The early-2000s tech hoodie-and-jeans look was a deliberate signal of meritocracy and indifference to clothes, but it became its own conformist uniform where everyone mirrored each other.

“There was a moment in the tech industry in the early 2000s where the hoodies and jeans uniform was a way to signal, I don't care about clothes. I'm like the Wizkid, you know, kind of hacker that's reshaping the economy. All I care is about meritocracy and skills. But it just so happens that over time within that industry, everyone started to also dress the same.”

The tech hoodie was itself a uniform signaling 'I don't care'

The early-2000s tech hoodie-and-jeans look was a deliberate signal of meritocracy and indifference to clothes, but it became its own conformist uniform where everyone mirrored each other.

“There was a moment in the tech industry in the early 2000s where the hoodies and jeans uniform was a way to signal, I don't care about clothes. I'm like the Wizkid, you know, kind of hacker that's reshaping the economy. All I care is about meritocracy and skills. But it just so happens that over time within that industry, everyone started to also dress the same.”

Sprezzatura: conceal the effort

A 16th-century Italian concept for menswear: dress (or act) in a way that hides the effort you put in, so the result looks effortless and natural. Beau Brummell reportedly spent hours tying his cravat then walked out as if he'd fallen into his clothes.

“But sprezzatura in a men's style sense is basically to dress in a way that conceals the effort that you've put in. But the concept goes way back before this writer. It goes back to even Brummell, who is largely understood to have shaped much of modern men's style. And Brummell used to spend hours tying his cravat, his white cravat, which is kind of like a neckerchief.”

Ralph Lauren flagships are built like theme-park 'worlds'

Unlike normal Ralph Lauren stores, the flagships are designed like EPCOT, with distinct fantasy 'worlds' (ranch world, old-money world) that imbue shoppers with a fantasy and sell an identity, not just a product.

“You go through a Ralph Lauren flagship, there's like the ranch world, there's the old money world, there's, you know, there's all these different worlds that he creates around costumes. And it's because he knows how to imbue you with both that fantasy and to kind of use that language and design to reference different social ideas and identities.”

Win by occupying the gap between trend reporting and academia

Derek Guy positions his writing as smarter than basic trend reporting but more accessible than dense academic fashion writing, treading water where few writers compete, which he credits for his rise.

“And I, I try to do something that's a little bit smarter than just like basic trend reporting or fashion writing, but it's a little bit more accessible than academic writing. And then I also tread this water where not a lot of people are treading. And I think that kind of helps. I think it helps to be in this very specific space.”

Steal thisFind the unoccupied middle ground between shallow popular content and inaccessible expert content, and own it.

Win by occupying the gap between trend reporting and academia

Derek Guy positions his writing as smarter than basic trend reporting but more accessible than dense academic fashion writing, treading water where few writers compete, which he credits for his rise.

“And I, I try to do something that's a little bit smarter than just like basic trend reporting or fashion writing, but it's a little bit more accessible than academic writing. And then I also tread this water where not a lot of people are treading. And I think that kind of helps. I think it helps to be in this very specific space.”

Steal thisFind the unoccupied middle ground between shallow popular content and inaccessible expert content, and own it.

The local clothier died, dumping the burden on the consumer

Historically men dressed well because a local clothier outfitted them and handled all the tailoring; that role and its customer loyalty have disappeared, so men now buy piecemeal from different brands online with no one guiding them.

“Those clothiers have disappeared and customer loyalty is no longer there as well. So whereas a man used to go to his tailor and would introduce his son to his tailor, now men shop from different places, not only different aesthetics, but they might buy their jeans from a jean company, shirts from a shirt company, socks from sock company.”

The Paradox of Choice by Barry Schwartz

Barry Schwartz's book opens with him buying the best jeans of his life at The Gap yet feeling more unsatisfied than ever, because the flood of options made him doubt his choice. The thesis: people are often better off with fewer, constrained options.

“His name is Barry Schwartz, and he wrote a book called The Paradox of Choice. That book opens with a story of how Schwartz enters The Gap and is shopping for a pair of jeans, and the sales associate asks him, do you want washed, raw, rinsed, white, dark blue, slim fit, straight, slim straight, tapered, you know, baggy, athletic cut? And he gave him all these options. And he said he walked out that day from the Gap with the best pair of jeans he's ever bought, but he was left more unsatisfied than he's ever felt because just knowing that there were so many choices made him question the choice that he made that day.”

The Paradox of Choice by Barry Schwartz

Barry Schwartz's book opens with him buying the best jeans of his life at The Gap yet feeling more unsatisfied than ever, because the flood of options made him doubt his choice. The thesis: people are often better off with fewer, constrained options.

“His name is Barry Schwartz, and he wrote a book called The Paradox of Choice. That book opens with a story of how Schwartz enters The Gap and is shopping for a pair of jeans, and the sales associate asks him, do you want washed, raw, rinsed, white, dark blue, slim fit, straight, slim straight, tapered, you know, baggy, athletic cut? And he gave him all these options. And he said he walked out that day from the Gap with the best pair of jeans he's ever bought, but he was left more unsatisfied than he's ever felt because just knowing that there were so many choices made him question the choice that he made that day.”

How to spot a quality leather dress shoe

Quality dress shoes have a Blake stitch or Goodyear welt on the sole and full-grain leather uppers, so they age better, last longer, and can be resoled, versus glued-on soles with corrected-grain leather that flakes and ages poorly.

“If you buy leather dress shoes made with a Blake stitch or Goodyear welt on the sole, and the uppers are made from full grain leather, those shoes will age better, last longer, and they can be resoled.”

Steal thisBuy dress shoes with a Goodyear welt and full-grain leather so you can resole them and they age well.

Judge clothing quality like food, not engineering specs

Derek Guy argues the real test of quality isn't reading construction specs off a sheet but three holistic questions: Are you excited to wear it today and in 10 years? Will it last? Does it fit and flatter you? Treat it like tasting food, not buying electronics.

“But the real measure of quality should be, are you excited to put it on today? And do you think you'll be excited to put this on 10 years from now?”

Steal thisBuy clothes you're excited to wear, that fit and flatter, and that will last, rather than chasing construction specs.

Buy ready-to-wear, not bespoke, even if you think you need custom

Derek Guy's top reason to choose ready-to-wear over a custom suit: you can try it on and put it back on the rack with zero consequences. A custom garment can cost $2,000 to $8,000, is final sale, and may not fit or please you once made.

“And then at that point you've just spent anywhere from, you know, like $2,000 to $8,000 possibly for a garment and you can't return it. Um, whereas with the ready-to-wear garment, you can try on a $10,000 I don't even know if $20,000 suits exist for ready-to-wear, but if they did, you could try it on and put it back on the rack and nothing happens. And that's the number one reason.”

Steal thisDefault to ready-to-wear you can return; use try-ons to learn your silhouette before ever committing to bespoke.

Vet a tailor by their customers on Instagram, not their own outfit

Many tailors are technicians, not stylists, so they often dress plainly; don't judge them by their clothes. Instead check the tailor's Instagram tag section to see whether their customers' suits fit well, especially customers with a build similar to yours.

“So if the customers come out and they all are wearing suits that don't fit, the chance of you getting a good suit from that tailor is very low. But if all the customers walk out and their suits fit perfectly, and especially helps if the customers walk out or have a similar build as you.”

Steal thisBefore hiring a tailor, scan their Instagram tagged photos for customers your build whose suits fit perfectly.

Every hobby's three stages end in 'nirvana'

From Perfumes: The Guide, the journey through any hobby has three stages: exploration (mapping the terrain), rigid-rules dogmatism (strong opinions about how everything must be), and finally nirvana, where you know the rules but ignore them and just like what you like, even if it's cheap.

“And then the third final step is what she feels is nirvana, where you know the rules, but you're not like strict about them. And you just like what you like. So I think that's actually pretty true for a lot of things, whether you're into motorcycles or whether you're into, you know, you're a foodie or you're into fountain pens, is that people start with an exploration stage.”