derek guy Profile picture
Jan 17, 2025 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

Jul 12
I will tell you how to find a tailor. 🧵
For the purposes of this thread, I will assume you mean an alterations tailor, which is someone who alters clothes you bought from a store. I will not cover bespoke tailors, who are people that make clothes from scratch. That kind of discussion goes beyond what I can cover here. Image
Like any trade, the clothing business can involve a bit of insider baseball. To find a good tailor, call a few stores that sell high-end clothes. For men, these will be suits that retail for $3,000 and up. For women, it will be things like suits, eveningwear, and bridal gowns. Image
Read 16 tweets
Jul 2
Stephen Miller's suit here shows one of the biggest problems with men's tailoring today. 🧵
I should first emphasize this thread is not meant to body shame. I mean that sincerely. Few men are built like Adonis, so when shopping for clothes, most will have their own fit challenges, including muscular figures. This thread is only meant to highlight a tailoring issue.
Let's first do an experiment. Which suit do you think looks better?

Left or right? Image
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Read 18 tweets
Jul 1
Here's an explanation of when you can wear a suit jacket on its own. 🧵
But first, let's play a game. Here are two men wearing gray tailored jackets with blue pants. Which outfit looks better to you? Ignore physical attributes of the people underneath and focus on the outfits. Then reply with your answer. Image
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If you said the right looks better, then we have the same taste. In this case, we can again go back to history to understand our views.

As I've said before, our notions in traditional men's tailoring largely derive from Britain, where suits and sport coats were invented.
Read 16 tweets
Jun 28
If you're looking for fabrics that you can wear in the summer, it's useful to consider three things: weight, weave, and fiber. If you only pay attention to one of these dimensions (say, linen), you will miss the bigger picture.

Let me show you. 🧵
If you're shopping for shirts, then some of the better summer materials include linen, seersucker, madras, and very lightweight, open weave cottons. In the photo below, you can see a swatch of voile, which is a featherweight 2/3oz cotton that's so open, it's almost sheer. Image
You can see here why most men don't wear it. Without a jacket, the material can almost be indecent (although it's more forgiving in non-white colors like light blue). For this reason, some tailors double up the front, like you see on the right, but this limits the breathability. Image
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Read 18 tweets
Jun 26
As a general matter, my advice isn't really "go to this store" or "buy this brand." Rather, I encourage people to think about clothes in a certain way.

Let me show you how to shop for a good suit. 🧵
My advice isn't really about brands or stores because everyone has unique fit challenges they have to solve. Perhaps you have forward pitched shoulders or a barrel chest. Or maybe you have big thighs and a prominent seat. No single suit will work for everyone. Image
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When shopping for a suit, it helps to know how they're made. Suit jackets and sport coats are unique in that they're made from layers of haircloth, canvas, and padding, which are shaped through darts, pad stitching, and ironwork. This is how you get the 3D shape. Image
Read 18 tweets
May 26
A lot of attention is paid to craft traditions in Western Europe and North America, such as handsewn Hermes leather goods and bespoke Savile Row suits. But the uneven focus leads some to believe that things made outside of these places are low quality.

This is not true. 🧵 Image
When I was on a menswear forum, there was a guy whose style I greatly admired. Like others on the forum, Niyi Okuboyejo loved men's tailoring. He had a technical understanding of how a jacket should hang from the shoulders. He also knew how to put things together in a classic way Image
At the same time, he also knew how to do things in his own voice and style, but in a way that looked good and not haphazard. Sometimes this was about adding a funky tie; other times, it was playing with materials and silhouette. All of these are still suits and sport coats! Image
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Read 17 tweets

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