derek guy Profile picture
Jan 19, 2025 22 tweets 12 min read Read on X
Let's talk about how trousers should be hemmed. 🧵 Image
As usual, there are no hard and fast rules on hemming. Everything depends on the aesthetic you're working within. In some aesthetics, it's fine to have a very cropped leg (pic 1). In other aesthetics, it's fine to have a stacked leg (pic 2). Depends on the look! Image
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You can't be dogmatic about hemming bc much depends on the overall silhouette (including shape of pants). These silhouettes would look wrong if you didn't have fabric pooling around the ankles. Granted, there's a fine line btw intentional pooling and sloppy—so beware. Image
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But with classic men's tailoring—meaning outfits involving suits, sport coats, tailored trousers, and such—you're pretty safe going with one of two options. These are nicely outlined in this Fantasy Explosion tee for Bloomingdale’s 150th Anniversary souvenir capsule collection. Image
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There's what we'll call a "shivering break." Or what your tailor may know better as "no break." This means the trousers just kiss the top of your lace-up shoes (e.g., oxfords, derbies). This distinction is important bc slip-ons and boots can affect the break. Image
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A shivering break is nice because it creates a clean, uninterrupted line from the top of your pants to the hem. This is particularly good if you trousers have pleats (which, if you wear high-rise trousers, I think you should consider). Image
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One problem with a shivering break is that, depending on how the trousers are finished, there can be a gap between the back of your hem and the shoes, potentially exposing your socks. You can see this *almost* happening here, but not quite. Image
One solution is to ask for a slanted hem, or what's sometimes called "military hem." This can be done to plain hem trousers or cuffed trousers (although the second requires a bit more skill). This way, the front just kisses your shoe while the back covers any exposed sock. Image
The other option is to get a single break (on the Bloomingdale's t-shirt, they divide this into "small break" or "deep break." You may annoy your tailor if you ask for this level of specificity). This just means the trouser line breaks *once* over the shoe. Image
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Stylistically, a single break is the more conservative option. The danger is that, if you wear belted trousers, your pants will slip a little throughout the day (inevitable unless you wear suspenders). This can turn a gentle break into a deeper break. Be aware. Image
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Finally, there's the question of whether you should get cuffs. According to lore, King Edward VII popularized cuffs in 1890 when he started rolling up his trousers to keep the hem dry in bad weather. This is why some tailors still call this detail "turn ups." Image
In a 1922 issue of Vanity Fair, there were these illustrations of the Duke of York, Prince of Wales, and Prince Albert. The editors wrote: “In England, fashion never overrides the practical, and when it is raining in London, the Englishman’s trousers will always be turned up.” Image
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Given this history, cuffs are considered a casual detail—most at home on country suits (where one might trudge through the mud) rather than the slick worsteds worn for business in London.

Compare: cuffed country suit on the Duke; plain hem business suit on King Charles Image
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Today, the rule is much less strict. But cuffs should never be put on the most formal trousers, such as black tie rigs. Image
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To me, pleated trousers cry out for cuffs. Americans have also historically cuffed their trousers, as we're more casual than our British counterparts. If you're an American patriot and wearing American-style tailoring (e.g., sack suits), cuff your pants. Image
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Otherwise, it's up to you. Cuffed trousers have the advantage of putting a bit of weight at the end of your trousers, helping them hang better. IMO, this is especially nice as you walk, so your pants are flapping all over the place. Image
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Whether cuffed or plain hem, you can also ask your tailor to finish your pants with a strip of durable fabric tape. Ideally, this tape should be placed in such a way that it prevents the edge from fraying. It will also add a tiny bit of weight. Image
If you want to be annoying, you can also ask your tailor to finish your cuffed trousers with a buttonhole along the inseam and outseam. This will allow you to unbutton your cuffs and brush out any debris, which can otherwise wear down the material over time. Image
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A stylish graphic designer friend of mine once put matter of cuffs in font terminology. Cuffs, he said, are like the serifs on a font. They look right with very traditional outfits (pic 1), but more modern styles are often better uncuffed (pic 2). Image
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If you're unsure, always ask for cuffs. You can always take them out, but you can't put them in once your trousers have been hemmed. In terms of size, 1.75" is considered classic for cuffs. But a 2" cuff says "I like clothes." Image
Either way, the most important thing is to avoid this. If your pants look like this, get your trousers hemmed. If they were hemmed but eventually look like this, consider how your pants may be falling down. You may need a belt, suspenders, or a tailor to take in the waist. Image
Two corrections for clarity:

— The first tweet should say "crease," not "pleats." A shivering break (or more commonly known as "no break") can help create a clean line. Useful on creased trousers (as pictured).

— Second tweet should say "aren't flapping," not "are flapping." 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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