derek guy Profile picture
Sep 10, 2024 18 tweets 9 min read Read on X
Some style lessons from Gerard Basquiat, a Haitian immigrant whose son helped define the New York art scene and neo-expressionism. 🧵 Image
In tailoring, the term "gorge" refers to the seam that connects a jacket's collar to its lapels. This determines the shape and placement of the lapel's notch. The most classic placement creates a horizontal line running from the notch to the collar points.
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As a counter reaction to 1990s Armani, which had excessively low gorges, men's tailoring has seen gorges creep up over the last 20 years. It's not uncommon to see a notch lapel almost sitting on top of the shoulder. Or peak lapels flying off the shoulder.
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Something interesting about Gerard Basquiat's tailoring is that he always wore a notch that was basically level with his collar points. In this way, the notch is never too high or low; it's just classic. Compare to Ted Cruz's overly high gorge.
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Interestingly, Gerard carried this proportion into the later part of his life, bucking ready-to-wear trends. This again looks very tasteful (compare to the peak lapel a bit up-thread, which was flying off someone's shoulder). Image
People often think about clothes just in terms of sizes (small, medium, large). But a more defining aspect is their shape. Gerard's tailoring had tremendous shape, as evidence in the lapel's roll at the buttoning point. Compare to Cruz's lapel, which is pressed flat like panini
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Men are often reluctant to wear a higher-rise trouser because they don't want to look like an old man. But in a tailored outfit, the trouser rise serves a function: it covers up the bit of shirt fabric that would otherwise peek out from beneath the coat's buttoning point.
A suit is simply a garment where the jacket and pants have been made from the same cloth. This should create a coherent whole. When shirt fabric flashes beneath the jacket's buttoning point, it disrupts the line and spoils the sense of elegance.
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Gerard's sense of elegance is carried into his accessories. When wearing dark worsted suits, Gerard wore small dress watches on a leather strap. This looks much better than chunky sport watches, such as Cruz's Tag Heuer chronograph, which are better for casualwear.
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I suspect Gerard wore a Cartier Tank. His son's friend, Andy Warhol, also famously wore a Tank, once quoted as saying: “I don't wear a Tank to tell the time. In fact, I never wind it. I wear a Tank because it's the watch to wear.” Maybe Gerard suggested the style to him.
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Gerard's sense of quiet sophistication is also reflected in his ties. This spotted one reminds me of something Gore Vidal once wore while hanging out with JFK. Very demure, very tasteful.
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It's hard to talk about how to choose tasteful ties without spinning out an entire thread. But it's a generally good idea to stay away from overly shiny materials or busy designs. Jacquards, where a pattern has been woven into the silk, can also be dangerous. These are ugly:
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Most men today don't wear ties; they often look for ways to dress down tailoring. When doing so, I encourage you to never wear dress shirts with black buttons or contrast linings, as these look cheap and tacky. Go for something more classic, like Gerard's skipper collar polo.
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Additionally, when wearing knitwear, consider getting something that's a bit more textured. Texture is an easy way to add visual interest to an outfit, which is helpful when you can't layer with a coat or jacket.
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They can also be warmer and more rugged. Here's Gerard wearing a heavy woolen Shaker knit with a collared shirt and cotton pants while feeding his son at a park. A good dad outfit. Image
Ultimately, you will look great if you choose clothes that fit and flatter, develop an eye for details, and add dimensions such as tasteful textures and patterns when possible. Image
It also helps to keep clothes clean.
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To end, here are some of my favorite photos of Jean-Michel Basquiat. These were taken by Yutaka Sakano in 1983 when the artist was visiting Tokyo. As such, he's also wearing vintage items from Japanese designer Issey Miyake. Note the concept of "shape and drape" here.


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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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