derek guy Profile picture
May 5, 2024 13 tweets 9 min read Read on X
I see a lot of backlash here against men not wearing socks. IMO, this is a knee-jerk counter-reaction to the trend, which is as misguided as wearing something just because it's trendy. There is a better way to think about when you should wear socks. 🧵 Image
As always, do what you like. But if you're wearing a formal suit with formal shoes, I think you should wear socks. Not doing so is incongruous and confusing. Or, at the very least, looks dated and twee in a 2012 menswear way. Image
What do I mean by "formal?" I mean the clothes men used to wear for business. Today, people often think that any kind of tailored clothing—even something as simple as a shirt with buttons—is "formal." But in the past, there were finer distinctions. Image
Back when tailored clothing was more common, the standard business uniform was a smooth, worsted wool suit in a sober color such as grey or navy. This was worn with black or brown oxford shoes, which had facings sewn into the vamp for a sleeker look.
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But not all tailoring was meant for boardrooms. Men wore suits and sport coats made from more casual materials, such as linen, cotton, seersucker, Thornproof, corduroy, and such. They came in colors like white, brown, tan, olive, etc.


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Although the language of tailored clothing is a little lost today, people still understand the general meaning. They know that the outfit on the right is more casual than the one on the left. Think of the distinction between "business" and "leisure."
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Suits can be worn with oxfords, but they can also be worn with more casual shoes like loafers, derbies, or boots. This casualizes them further. Color and material also impact a shoe's formality: black is more formal than brown; calfskin is more formal than pebble grain or suede.
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So, when considering whether you can go sockless in an outfit, it's more useful to consider the overall coherence in terms of formality. Dark worsted suit with black oxfords? Wear socks. IMO, the outfit on the left looks better than the outfit on the right.
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But with more casual attire, you can go sockless. Here are four outfits in increasing order of formality, up to and including a casual suit. Notice that the clothes *and* shoes are casual. Casual clothes + casual shoe = can go sockless, if you want.


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It's not true that this is some totally new modern trend. Look through old photos of stylishly dressed men in warm locales in the mid-20th century, and you may see some bare ankles! Again, notice these are casual clothes *and* shoes.
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Some shoes—including non-Western styles, for my inclusive-minded followers—are also commonly worn without socks. These include espadrilles (a canvas Spanish slip-on), givehs (an Iranian slip-on), and huaraches (a Mexican sandal). You will look dumb wearing socks with espadrilles


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IMO, it's better to think about the total outfit—learning how to read details like language—than to think of things as universal rules. Or to react to things like "This is trendy, so I should wear it" or "It's too trendy, I should not wear it."


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As for the question I know is coming up: How do you prevent the stink? You can use Gold Bond powder, no-show socks, or terrycloth insoles. Or just ... you know ... live life. If sockless doesn't work for you, then maybe it doesn't work for you. But some outfits are fine sockles. Image

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More from @dieworkwear

Feb 7
Your suggestions are shit ass.

Let me tell you about backpacks. 🧵 Image
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Let's first establish good vs bad ways to think about style. The first pic is correct — style is a kind of social language and you have to figure out what type of person you are. The second pic is stupid bc it takes style as disconnected objects ("this is in" vs "this is out"). Image
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I should also note here that I'm only talking about style. I'm not here to argue with you about ergonomics, water bottle holders, or whether something accommodates your Dell laptop. I'm am talking about aesthetics.
Read 18 tweets
Feb 5
It's true that Canadian Prime Minister Mark Carney has a rounded back and forward pitched shoulders. But let me show you something. 🧵
Watch these two videos. Then answer these two questions:

— Which of the two men is better dressed?
— How does each come off?
I think Carney is better dressed, partly because his clothes fit better. Notice that his jacket collar always hugs his neck, while Pierre Poilievre's jacket collar never touches him.

Why do Poilievre's jackets fit like this? Image
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Read 11 tweets
Jan 18
The level of craftsmanship that goes into a lot of Japanese menswear simply doesn't exist in the United States. You can do this for many categories — suits, jeans, hats, etc.

In this thread, I will show you just one category: men's shoes 🧵
For this comparison, I will focus on Japanese bespoke shoemaking vs. US ready-to-wear. The level of bespoke craftsmanship shown here simply doesn't exist in the US, so a Japanese bespoke vs. US bespoke comparison would be unfair. US bespoke is mostly about orthopedic work.
So instead, I will focus on the best that the US has to offer: ready-to-wear Alden.

On a basic level, top-end Japanese shoes are better because they are handwelted, whereas Alden shoes are Goodyear welted. The first involves more handwork and can be resoled more often. Image
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Read 24 tweets
Dec 18, 2025
A story I found about Haiti:

In 1999, a group of Haitians were tired of political disorder and dreamed of a better life in the United States. So they built a small, 23-foot boat by hand using pine trees, scrap wood, and used nails. They called the boat "Believe in God." 🧵 Image
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In a boat powered by nothing but a sail, they somehow made it from Tortuga Island to the Bahamas (about a 90 mile distance). Then from the Bahamas, they set sail again. But a few days and some hundred miles later, their makeshift boat began to sink. Image
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The men on the boat were so dehydrated this point, one slipped in and out of consciousness, unable to stand. They were all resigned to their death.

Luckily, they were rescued at the last minute by the US Coast Guard. Image
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Read 5 tweets
Dec 1, 2025
After this post went viral, I called Caroline Groves, a world-class bespoke shoemaker, to discuss how women's shoes are made. I normally don't talk about womenswear, but I found the information interesting, so I thought I would share what I learned here. 🧵
First, who is Caroline Groves?

Footwear is broadly broken into two categories: bespoke and ready-to-wear. In London, bespoke makers, including those for women, are largely focused on traditional styles, such as wingtip derbies and loafers. Emiko Matsuda is great for this. Image
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In Paris, there's Massaro, a historic firm that has been operating since 1894, now owned by Chanel. Their designs are less about creating the women's equivalent of traditional men's footwear and more about things such as heels or creative styles. Aesthetic is still "traditional." Image
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Read 18 tweets
Nov 29, 2025
Earlier today, Roger Stone announced his partnership with a menswear company, where together they've released a collection of tailored clothing items.

Here is my review of those pieces. 🧵 Image
The line is mostly comprised of suits and sport coats, supplemented with dress shirts and one pair of odd trousers (tailor-speak for a pair of pants made without a matching jacket). Suits start at $1,540; sport coats are $1,150. One suit is $5,400 bc it's made from Scabal fabric Image
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Let's start with the good points. These are fully canvassed jackets, meaning a free floating canvas has been tacked onto the face fabric to give it some weight and structure. This is better than a half-canvas and fully fused construction, but requires more time and labor. Image
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Read 24 tweets

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