derek guy Profile picture
Aug 26, 2025 19 tweets 11 min read Read on X
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

Thus, when people say my preferences make men look "old," I don't take it as an insult. I think older men have a more intimate connection with the period in which men looked best in tailoring, so it's great if something looks like a style only an old man would wear. Image
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My favorite shoes tend to be the sort of thing associated with older men, such as tassel loafers. They look great with suits or sport coats, especially garments in fusty materials such as tweed and flannel. Oxford cloth button-downs + tweed jackets + tassel loafers = great. Image
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I like derbies for the same reason: they don't have the sleek formality of oxfords, but they're more versatile, which makes them useful in a dressed down world, where you might want to tone down your tailoring. But derbies come in many flavors: plain, cap toe, wingtip, etc. Image
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IMO, plain is too plain. Cap toe is equally boring. And a wingtip is too gentlemanly.

This leaves the split toe, which I like partly because they are favored by men whose style I admire, such as Bruce Boyer and Yukio Akamine. Image
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What is a split toe?

A split toe is simply a derby with an apron front (sometimes called a lake). And going down the middle of the toe is a seam, giving the style its name. Today, this is considered a dress shoe, most often worn by older men in "dress clothes." Image
But this was not always so. At the famous John Lobb of St. James in London, you'll find bespoke shoemakers referring to this style as the "navvy cut." The term navvy refers to a kind of navigational worker who built the infrastructure that made the Industrial Revolution possible Image
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Starting in the 18th cent, Britain began building big canals, which allowed for the cheaper transport of goods and coal. The actual work of building these canals fell on navvys (navigators), who were often recruited from the rural poor: displaced peasants, farm workers, etc. Image
These navvys built much of the nation's infrastructure, such as railways, roads, canals, tunnels, and sewers. When London's population swelled from one to seven million in the 19th century, the city struggled with overflowing sewage in the Thames River. The navvys solved this. Image
These navvys wore split-toe derbies because the open facings allowed for a more comfortable and forgiving fit. The seam going down the middle of the toe also allowed the shoemaker to save material by creatively cutting the pattern, resulting in cheaper footwear. Image
Modern split-toes are unique in that they often show a bit of craftsmanship. On the left, we see what's colloquially known as a "pie crust apron," which can only be made by hand. On the right, we see a machine-sewn apron. IMO, the handmade version is much better looking. Image
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This wavy, crimped seam is made by attaching a bit of waxed thread to a flexible boar bristle. The shoemaker tunnels the thin bristle about halfway through the leather, pushing it out to the other side, and then repeating the process. Hence the name "split and lift" stitch. Image
The actual split toe seam is done with the same technique, only on the reverse side.

In bespoke, some makers will offer a braided stitched apron, as you see here. These are not split toes, just derbies, but the technique can be applied to any apron. Shoes by Nicholas Templeman: Image
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Details can make a split toe more or less formal: material (smooth calf, grained calf, suede), color (black, dark brown, tan), and shape (sleek vs rounded). Here are two split toes, but considerably different in vibe. Second is easier to wear with jeans. Image
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In fact, there are plenty of split toes that would not look out of place with something as causal as a chore coat, which is not something you can say about an oxford. The chunky, rounded silhouette here with a thicker sole throws the design back to its workwear origins. Image
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To me, Seiji McCarthy in Tokyo makes particularly handsome split toes. They are casual enough to be teamed with jeans, but wouldn't look out of place with gray flannel trousers and a tweed sport coat. Or even many suits. Image
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There are so many variations of this design. Ultimately, the toe seam will read as "old man" to some, a mark of connoisseurship to others (meaning, menswear nerds). I love them bc I associate them with men whose style I admire. And a beautiful working class history. 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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