derek guy Profile picture
Oct 24, 2024 22 tweets 13 min read Read on X
Had this saved in my bookmarks because I wanted to answer it. Funny enough, I think Senator Sheldon Whitehouse is one of the better dressed US politicians, but only in a very specific way that will appeal to a very small group of people. 🧵
First, let's look at some photos of Senator Whitehouse. Do you think he's well-dressed? What do you think of his style? Please make your judgements before reading on, as I don't want my commentary to color your views. Image
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Personally, I think he dresses well. I like his use of gabardine and tweed in addition to typical dark worsteds. I like that he wears colors such as olive, rather than only navy and grey. He has good taste in ties and layers with Shetland knits. His clothes have good proportions.
Most of all, I notice his collars—the style, shape, proportions, construction, and material. To understand why it's great we must go back, once again, to the turn of the 20th century. Image
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In 1896, John E. Brooks—grandson of Brooks Brothers founder Henry Sands Brooks—noticed that some English polo players wore little buttons on their shirt collars to prevent the points from flapping in their face while playing. Image
He thought this was charming, so he sent a sample back to his tailors in NYC and asked them to copy it exactly. In 1900, Brooks Brothers put the new collar style on their ready-made sport shirts. These were called “polo shirts” for their polo-inspired collars. Image
These shirts were first made with white cotton cheviots (a stout twill) and then later a thick cotton basketweave known as oxford. Hence the oxford-cloth button-down was born.

The shirt was an instant classic. By 1915, it was a staple on East Coast colleges and then spread West. Image
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Since Brooks Brothers clothed that upwardly mobile class of Americans who saw their fortunes rise with industrial capitalism, many of their clothes took on status. Their customers were the kind of people who sent their kids to private schools that fed into Ivy League colleges. Image
The stuff these people wore—three-roll-two sack coats, silk rep ties, penny loafers, tweed jackets, and button-down collars—became the hallmarks of Ivy Style. It's easy to poo poo this style today as reverse snobbery, but this language forms the ABCs of American style. Image
You can draw a line from what Brooks Brothers introduced in the early 1900s to Ralph Lauren's aesthetic by the close of the century. Today, brands such as Aime Leon Dore still rely heavily on that language, but they remix it to feel fresh. Image
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The button-down collar in particular became a short hand for a kind of American. Bob Newhart named his 1960 comedy album after it. Mary Mccarthy’s 1942 short story “The Man in the Brooks Brothers Shirt” is about a woman who falls for a stylish executive on a Pullman train. Image
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For much of the 20th century, this collar was of a symbol of all that was good: casualness, youth, education, trustworthiness, dependability, sport, and professionalism. They were something a man could wear in the country or city, in sport or business, on weekdays or weekends. Image
It also represented more than the old money WASP customers. Non-Americans such as Gianni Agnelli wore it. African American jazz musicians gave it a sense of cool. Miles Davis wore it on the cover of Milestones. Image
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Much like Levi's 501s, Brooks Brothers's button-down has changed in the last ~125 years. It was originally put on pullover shirts (pic 1) before going onto coat-front styles (pic 2). It lacked a chest pocket before the 1950s (pic 3). Hems have also changed (pic 4). Image
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But the best versions—the ones beloved by American style enthusiasts—had a totally unlined collar. In a typical shirt collar, there's something here to give the collar structure. Brooks has gone in and out of using interlining, but the softest ones were unlined. Image
Not having an interlining means the collar is softer, more comfortable, and frankly messier. The collar shifts and wrinkles when you move. But therein lies the charm. American style—from sack suits to streetwear—has always been about a kind of calculated "I don't care" attitude. Image
When combined with the right fabric, cut, and proportions, you get a beautiful collar roll that looks like the outline of an ascending angel's wings. Look at that gentle S-shape! Image
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People who are into classic American men's style furiously debate this stuff online. There are long threads about where to get shirts like those mid-century Brooks Brothers originals, handwringing over the presence of interlinings, arguments about orthodoxy, etc. Image
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The thing about Senator Whitehouse is that he often wears an oxford cloth button-down in those exactly correct proportions, material, and details. Image
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It's even more evident when you see people get it wrong. RFK Jr.'s collar points are too small (no roll). Ron Johnson and Bernie's collars are too controlled (likely lined). Roger Stone's buttons are placed too far apart, making his collar look like it's giving birth to a tie. Image
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Senator Whitehouse's collar is exactly like those mid-century originals—tasteful spread, beautiful roll, imperfect wrinkles that convey a kind of casual American spirit. Image
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It's a wonderful, distinctly American look, but admittedly one that will only appeal to the kind of guys who spend all day reading menswear blogs and forums. It makes me happy to see one "in the wild" worn by someone who likely never even thought about his choice. 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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