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

Oct 8
Have you ever noticed that old clothes online sometimes look better than old clothes in your closet?

Why is that? 🧵 Image
It's often said that clothes were better made in the past. This is true to some degree, although the discussion is often narrowly focused on durability.

In this thread, I'll focus on something else: how clothes age, which affects how long you enjoy wearing them. Image
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I'll give you some examples.

A hundred years ago, denim was mostly woven on slow shuttle looms, which produced a narrow-width fabric that was finished with a self-edge (selvedge). This fabric was taken straight off the loom and given to factories.

YouTube bluelabamsterdam8250
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Read 17 tweets
Oct 4
This is a great question.

How much does a handmade necktie cost? And why does it cost as much as it does? 🧵
A couple of years ago, I saw Jesse Watters on Fox News say that Otaa ties are "the best ties in the world."

So I bought one.
Otaa is an Australian neckwear company that has been showing up a lot in American politics. Along with Jesse Watters, they appear to be favored by RFK Jr. and his top deputy, Jim O’Neill. Image
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Read 25 tweets
Sep 26
Let me tell you a beautiful story about this couch. 🧵

IG msviciousdesign
Some will recognize these motifs as Mughal paintings, which flourished on the Indian subcontinent sometime between the 16th and 18th century. But menswear nerds will recognize them as something else: Drake's of London.

Left: thrifted couch
Right: Drake's of London scarf Image
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Drake's of London is a menswear label that started in the 1970s, initially with men's accessories, but having since grown to a full line of apparel. They are known for many things, but this print is perhaps their most famous. It appears on scarves, pocket squares, and even ties. Image
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Read 24 tweets
Sep 16
Style lessons from Robert Redford, one of the most stylish men in the last century. 🧵 Image
A tailored jacket continues to be one of the most flattering things you can wear. However, for it to look good, it has to fit right. That means a jacket that bisects you halfway from your collar to the floor when you're in heeled shoes. Also trouser + suit jacket silhouette flows Image
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It also helps to know how to use this visual language, especially with regard to ideas about formality. For instance, a dark business suit cries out for a tie. If you don't want to wear a tie, try a more casual garment, like a sport coat. Image
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Read 19 tweets
Sep 15
Someone yesterday asked me why someone would ask a tailor to make a polo coat in such a way to imitate the look of a machine-made garment.

The answer holds a beautifully little story about the difference between European and American style. 🧵
Let's start with a test. Here are two tan polo coats. One is machine-made. The other is handmade. Can you guess which is which?

Please answer before moving on. Then you can scroll through the answers to see whether most people got it right. Image
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The first coat is machine-made. It's from an American ready-to-wear company called J. Press. The second is handmade. It's from a London bespoke tailoring house called Anderson & Sheppard.

You can spot the difference by how the edges are finished. Image
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Read 19 tweets
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

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