derek guy Profile picture
Apr 21, 2025 21 tweets 12 min read Read on X
Rumors are going around that Pete Hegseth might be on his way out. I don’t know if that’s true, but just in case, I want to do a thread on his style. To me, Hegseth’s wardrobe reflects a common pitfall guys fall into when they first start caring about clothes. 🧵 Image
When men start dressing with more intention, they often fall into the trap of cranking every knob to 11—volume, gain, treble, bass. The thinking is: more = better. But like in music, maxing out every setting doesn’t lead to clarity—it leads to noise. Image
We see this in how Hegseth dresses. His belt buckle is USA. Pocket square is USA. Socks are USA. Open up his jacket and what do you see? USA. Image
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If there’s ever a chance to customize, he takes it—monogrammed shirt cuffs, contrast buttonholes, lapel pins galore. No flourish is left behind. Image
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With dark worsted pinstripe suits—the hallmark of conservative business dress—he skips the standard black oxfords and opts for bright tan shoes, simply because they catch the eye. And to drive it home, he throws on yellow socks to match his tie. Image
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The problem is that his clothes don't fit very well, and no amount of flourish or flair will hide this fact. He commonly wears clothes that are slightly too tight, sometimes resulting in a collar gap, as seen here

Trousers are a bit too low rise, sometimes revealing the flash or shirt fabric beneath the coat's buttoning point. Or, at times, his necktie. Image
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No matter your personal style, the most important elements of any outfit are fit and silhouette. Without those, everything else falls flat. Compare the more classic proportions on the left: longer jacket, wider shoulders, lower buttoning point, higher rise pants. Image
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Tailoring is meant to flatter the body, not reproduce its lines. On the left, the llama has a human-like shape, even though that’s not its natural build. Hegseth’s tailoring hews too close to his actual build, which makes things look a bit tight. Image
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Even in plain worsteds and without a single flourish, an outfit can look great if the tailoring is right. The first priority should always be fit and silhouette—everything else is secondary.

Examples below from Atelier Willow and Assisi, both in South Korea Image
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The second step is to think of your outfit as a whole—not just as a collection of pieces that excite you individually. Tan double monks might be fun, but they’re too casual for a charcoal pinstripe suit. Historically, tan shoes were for leisure, not business. Image
Business attire calls for "serious" shoes, typically lace-up oxfords in conservative colors such as black, dark brown, or mid-brown. They signal formality and restraint, which is exactly what conservative business dress is meant to convey. Image
It's admirable that Hegesth likes to wear his patriotism on his sleeve (or all over his body). But everything comes off very ham-handed and with no appreciation for this country's great clothing history. (Also, belt with black tie is .... very inelegant). Image
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I'd like to suggest some more sophisticated choices. Instead of an aggressively cut back spread collar (awful, tacky, too European) with a Windsor knot, he should honor this country's history with a button-down collar worn with a four-in-hand. Image
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The button-down, of course, is that style that Brooks Brothers introduced in the early 20th century and soon became a hallmark of classic American male dress. When cut properly, the collar points are long enough to create a soft, angelic roll. Can be worn with or without a tie. Image
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He should also ditch these suits. In the first pic, we see stiff, padded shoulders. In the second image, we see side vents (the flap at the back). And in the third pic we see machine-made pick stitching—the hard dimples along the lapel's edge. Image
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Those dimples are made to imitate the look of a handsewn European suit. Since the lapel is made from multiple layers of material, European tailors finish the edge with this gentle pick stitch. This results in soft dimples, not hard ones. Can look lovely if done well.
American clothiers typically finish their suit jackets and sport coats with a machine-sewn lapel, but they do a straight line so that there's no contrivance. See how the edge here doesn't have dimples—it's just a straight line of machine sewing. Doesn't try to imitate hand sewing Image
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Classic American tailoring is also distinguished by its soft shoulders, hook vent, and dartless front, which gives the jackets straighter sides. Image
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This is the style that carried American men from the hopping jazz clubs of the Roaring 20s through the Great Depression and onto campuses of a booming postwar America. The style suits any build, which is what makes it so democratic. Image
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As you start to dress with more intention, I encourage you to:

1) Prioritize fit and silhouette
2) Resist the temptation to turn every knob up
3) Think of dress as social language informed by history

IMO outfit on left is more sophisticated and American than one on the right. 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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