derek guy Profile picture
Jan 17 16 tweets 9 min read Read on X
I disagree. This outfit is terrible and I will show you better ways to wear a polo. 🧵 Image
It's hard to look good in a polo for all of the same reasons it's hard to look good in just a button-up dress shirt or a t-shirt. The garment typically has no silhouette. Polos are relatively simple garments with straight seams and a short placket. Image
Like the fedora, it's also saddled with bad social connotations: rich pricks who run on family ties, golfing uncles, and business casual guys at networking conferences where there's plated cantaloupe. Image
Some people will point to stylish mid-century outfits worn by golf legends such as Arnold Palmer. But immediately, what do you see? The addition of layers, a distinctive silhouette (shape and drape), and the rule of thirds. Image
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What is the rule of thirds? The rule of thirds is not actually a rule, but just a gentle suggestion. It's the idea that an outfit can be made better if you break up the silhouette into thirds—top half is 1/3rd; bottom half is 2/3rds.

For example, which looks better? Image
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Bezo's outfit suffers from the same problem. It wouldn't matter if he tucked in his polo (this would look dumb with jeans, anyway). The pants are too low rise, so the outfit is broken into halves, not thirds. Image
I say this is a gentle suggestion because there are many good outfits that don't follow this "rule." But you can read more about the idea in this thread about t-shirts.

So how does one wear a better polo? The first is to get away from the business casual connotations. Instead of a simple button placket, as you'd find on a Lacoste polo, consider something like a skipper collar. Instead of pique cotton, consider another material. Image
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Here are these two ideas in action. Compare the build on Bezos vs Picasso. Bezos has a larger drop between his chest size and waist size. Picasso has less differentiation between shoulders, waist, and hips (he's kind of shaped like a tube). Image
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But which of these two outfits is more stylish? I think Picasso's. He's wearing a polo shirt made from a textured terrycloth and built with a unique collar. The outfit has aura. Image
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Another possibility is to get a polo built with a collar band. Most polos are built in such a way that the collar flops over. We see this in other photos of Bezos from the same day. Notice how the collar simply folds over. Image
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Some polos, however, are built with a collar band, like you'd find on a button-up shirt. The collar band connects to the shirt's body and fold-down collar, allowing the collar points to stand up and behave like a dress shirt. This can be useful for layering. Image
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This is important because polos are one of the easiest ways to dress down a tailored jacket, so long as you don't get the ones Bezos is wearing. And a tailored jacket is important bc it adds a finishing layer and creates a distinctive silhouette. Image
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If you can't wear a tailored jacket, or if you don't want to look overly traditional, you can always go back to the original points above: distinct collar, unique fabric (not pique cotton), rule of thirds. These outfits look good bc polo is not suction fit. Image
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IMO, many people who purport to be interested in style are actually interested in other things—body types, position in society (power, wealth), and ideas about prestige. But to me, this outfit is vanilla bland. Does not matter if it's on a buff body. Outfit is still boring. Image
I only write about style, not about how to look "hot" (assuming your intent is to attract a partner). But I will throw it to others. Do these people (or outfits, if you wish) look "hot?"

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More from @dieworkwear

Sep 15
I disagree that Obama wore "slick suits."

Let me tell you about Obama's tailoring. 🧵
I've seen people here suggest Obama was a stylish president. I couldn't disagree more. Outfits like these read better in 2025, but during the slim-fit, Euro style craze of his presidency, Obama was routinely panned for his "frumpy dad style." See Vanity Fair. Image
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His style transformation really came post-presidency. I suspect, but don't have proof, that this is partly the influence of his wife, who is quite stylish. Even his suits look better now. See clean shoulder line + shirt collar points reaching lapels + nice four-in-hand dimple. Image
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Read 16 tweets
Sep 9
Although it's rarely expressed in outright terms, people often use a very simple heuristic when solving fashion problems: they wish to look rich, which is often disguised as "respectable."

I will show you why this rarely leads to good outfits. 🧵 Image
In 1902, German sociologist Georg Simmel neatly summed up fashion in an essay titled "On Fashion." Fashion, he asserted was simply a game of imitation in which people copy their "social betters." This causes the upper classes to move on, so as to distinguish themselves. Image
He was right. And his theory explains why Edward VIII, the Duke of Windsor, was the most influential menswear figure in the early 20th century. By virtue of his position and taste, he popularized soft collars, belted trousers, cuffs, Fair Isle sweaters, and all sorts of things. Image
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Read 25 tweets
Sep 6
It's funny to see people imbue traditional men's tailoring with their own prejudices. They assume every man who wore a suit in the far past must be a staunch conservative like them. The truth is much more complicated. 🧵
This bias, of course, stems out of the 1960s and 70s, from which many of our contemporary politics also spring. I don't need to belabor this point because you already know it. The framing is neatly summed up in this Mad Men scene — the rag tag hippie vs man in a suit.
Thus, people assume that men in suits must always be part of the conservative establishment. But this was not always so. The suit was once a working man's garment. When Keir Hardie, founder of the Labour Party, arrived for his first day in Parliament, he wore a suit. Image
Read 17 tweets
Sep 6
Which of these two jackets do you prefer?

There's no "right" or "wrong" answer here, so feel free to go with your gut. I will then give you my views below. 🧵 Image
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In men's tailoring, the area below the jacket's buttoning point is colloquially known as the "quarters" among menswear enthusiasts. Or the "front edge" by actual tailors. These terms refer to the edge of the coat, connecting to lapels. Image
Some suit jackets have very closed quarters, such as you see on the left. In this way, the jacket forms a Y-shaped silhouette.

Other suits have open quarters, such that the front edge sweeps back on the hips, as you see on the right. This forms an X-shaped silhouette. Image
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Read 6 tweets
Aug 30
Here are ways to dress up in the summer if you wear menswear. 🧵
We will start with the most formal and work our way down, so that you can adjust things in ways that make sense for you.

The first and most obvious choice is to wear a soft-shouldered suit rendered in a material such as linen or seersucker. Seersucker can even be tonal (pic 4) Image
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However, when it comes to dressing for the heat, it's important to remember that the fabric's weight and weave are more important than fiber. A 10oz tropical wool — known for its open weave — will wear cooler than a densely woven 14 oz linen because it allows air to pass through Image
Read 23 tweets
Aug 26
I will tell you why I think the split-toe derby is the greatest dress shoe of all time. 🧵 Image
Let's first start with some terms. The term oxford refers to a footwear style where the facings have been sewn into the vamp. By contrast, the term derby refers to a style where the facings sit on top of the vamp.

On the left, we see an oxford. On the right, we see a derby. Image
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I believe that men wore tailored clothing best from the 1930s through '80s. If you share this premise, there are certain ideas about how an outfit should be put together, such as how oxfords look best with suits, while derbies go with suits or sport coats

Read 19 tweets

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