derek guy Profile picture
Apr 14, 2024 13 tweets 8 min read Read on X
The jacket is pretty good in that there's minimal waist pulling, and the collar hugs his neck even as he moves his arms. The main issue is that the sleeves are too slim, causing them to catch on his arms. Compare this to the second pic, where sleeves drape cleanly.
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If I were in charge of his fitting, I would also shorten both the shirt and jacket sleeves so they don't look like they're enveloping his hand. The slimness of his jacket sleeve is also causing the French cuff to push out against the jacket. Not ideal
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Compare that to these sleeves, which are

1. Fuller
2. Drape cleaner
3. At the correct length, such that they only show a sliver of shirt cuff and end around the person's wrist bone.

Tailor the shirt first, then adjust the jacket according to the shirt.


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The main issue I see with a lot of Elon's tailored outfits is that he likes to wear cowboy boots, which is fine as a concept. But his trousers are often too slim for the boots. This results in the tops (the boot's shaft) pushing out against the trouser legs.
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We see this happening here. The tops of the cowboy boots are pushing against the trouser legs, which is then causing the trousers to crumple. This is not very elegant.
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Compare the above to Bush's black tie + cowboy boot combination. The fuller trousers drape more cleanly across the tops of the boots. This looks more elegant.
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Cowboy boots have a very high vamp (the part of the shoe that covers the top of your foot). In other words, the boots slope up very high. If your trousers are too slim or have not been properly tailored, they will catch and crumple. See the fullness of GWB's trousers here: Image
If Elon wants to wear slim trousers with boots, he should get side-zips. Cowboy boots need to have wide tops. Otherwise, you would not be able to slip your foot in. However, side zips can be opened and then closed via the zipper, making the shaft slimmer. These are from Tecovas:
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In fact, in the 1970s, Frank Sinatra had dozens of side-zips made for him by various bespoke shoemakers based in California and London. He wore these on stage with dinner suits (aka tuxedos) and dark worsted suits while singing. They also had a higher heel.
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In this video, you can see a young Bill Bird at Peens, a tree-making operation once owned by John Lobb (the bespoke firm in London, not the ready-made firm in Paris). Bird is failing to be discreet about their famous customer as he shows off Sinatra’s lasts.
However, Elon should wear fuller trousers. Doing so will create a more streamlined silhouette, going from his jacket to his trousers. This will give the impression of a more harmonious whole rather than breaking the top and bottom halves into distinct blocks.
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Black tie is fundamentally party clothes, so they can be fun. You can wear tartan velvet dinner jackets with Prince Albert slippers or Belgian loafers if you want. But a governing principle should be elegance. Widening sleeves and pants here will help in this regard.


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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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