derek guy Profile picture
Mar 5, 2024 25 tweets 11 min read Read on X
Let's talk about how to buy better dress shirts. 🧵 Image
When Brooks Brothers invented the ready-made suit in 1849, they set into motion a long chain of events that eventually led to the near collapse of custom tailoring. In the early days, ready-to-wear was quite crude. Today, it's sophisticated. Most ppl should shop off-the-rack. Image
Dress shirts are the one area where custom tailoring still holds an edge over ready-to-wear, but much depends on how much you're already spending. Dress shirts can range anywhere from $20 to $2,000.

Pictured below: Brioni vs J. Crew Image
Above a certain price (say, $100), I think you should at least take a look at custom tailoring. This is partly because of how a shirt is built and how the fabric behaves. But to understand this, we have to review some very basic info about how clothes are made.
Every garment starts with a pattern, which is like its architectural blueprint. In bespoke, this pattern is ideally drafted from scratch. In made-to-measure, it's digitally adjusted off a block. In ready-to-wear, a company comes up with a pattern and hopes for the best. Image
When the pattern doesn't match your body, this shows up in the form of lines (e.g., puckering, pulling, wrinkling, etc).

Another fundamental rule about tailoring is that it's easier to hide a bad fit with heavier fabric, as the fabric will drape better.
Shirts have to be made from lightweight fabrics, which means that it's very easy to spot a bad fit. Notice all the pulling along this shirt's placket. This indicates the shirt is too tight. Image
You'll never completely eliminate wrinkles on a dress shirt because the fabric is so lightweight and your body moves (be reasonable). But just look at how clean this looks. This is a bespoke shirt from the French shirtmaker Charvet (one of the best in the world). Image
By contrast, a shirt is too tight when you see pulling across the placket and lines forming under the armhole, stretching across the chest. If you see a line going from the neck to the armhole, the shirt's shoulder slope doesn't match your shoulder slope.
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Nowadays, a bad fit often comes as a result of a shirt being too tight. But it's also possible for something to be too baggy. To be sure, bagginess can be a legitimate aesthetic. But compare the clean fit on the left with the baggy fit on the right.
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There's also the matter of style. As men's clothes have shrunk in the last 20 years, so have their details. It's common nowadays to find shirts with short, nubby collars. To me, a tailored outfit looks much better when the collar points reach the lapels. This creates clean lines
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A shirt collar is also typically made with some kind of interlining. Depending on how the shirt has been made, this can cause the collar to be very stiff, curl, or behave strangely. A good design is about finding the right interlining for the wearer's desired look.
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You can see the challenge: a good shirt is full but not baggy, cut for your body in a way so the fabric drapes cleanly. It should not cling or pull. The collar should have a pleasing appearance. A spread collar should reach your lapel; a button-down should have a full roll
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It can be difficult to get this in RTW because designers are constantly following trends and may not be making shirts that fit you. One solution to this is to find a custom shirtmaker if you can. Image
If you live in a major city, this is easy.

NYC: CEGO and Geneva
Los Angeles: Anto and Divij Bespoke
San Francisco: Tailor's Keep

Divij Bespoke, Ascot Chang, Budd Shirtmakers, and Dege & Skinner also tour the US for trunk shows. Contact them for their schedule. Image
Bespoke shirts typically start at ~$200. You can expect to be asked to buy a few shirts in the first order to justify the labor required to draft your pattern. If $200 is too expensive or you don't live in a major city, there's made-to-measure, which starts at ~$100 Image
Made-to-measure means your pattern was adjusted off of a block. Sometimes, this means you can't account for certain things, such as asymmetrically sloped shoulders (and everyone has a dropped shoulder, usually on the side with your dominant hand). But the fit can be pretty good
One of my favorites is @ProperCloth. They will make a custom shirt based on measurements of your body or your best-fitting shirt. They make everything: dress shirts, casual shirts, and even polos. You can also order fabric swatches first to see how they feel.
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I like their Soft Ivy Button-Down and Soft Roma Spread collars best. When you get your first shirt, wash and wear it a few times, then check how it looks. They allow free remakes on first-time orders, so you can nail the fit. They offer great value

🔗: blst.to/K9A9qRM

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Some people, including my friend @DavidLaneDesign, have also gotten good results through Luxire. They have a workshop in India, and they're flexible with regard to sizing and styling.
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When working with Luxire, I think it helps to know a little about tailoring. And to have some patience, as you're doing custom tailoring remotely. You may have to end up doing a remake or two before nailing something down. But they do good work.

🔗: blst.to/skms3aK

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Lastly, if you're looking for something a bit more bohemian, try Post Romantic. They have workshops in Pakistan's Punjab region, making them among the most price-competitive. I particularly like how they're able to source unique fabrics, such as handloomed indigo cotton & silks.
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My friend @urban_comp has used them with great success. Fit is less clean than Proper Cloth but these are also not supposed to be boardroom business shirts—they're fun, bohemian styles to be worn with casualwear

🔗: blst.to/bTwdiEG

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There are countless other options. Many reputable clothiers (e.g., @JPRESS_1902, @TheArmouryNYC, @HallMadden) have MTM shirt programs. Consider how much you value having someone in person to guide you through the process and fit you. It can be helpful to have that service.
The great thing about finding a custom shirtmaker is that once you nail the fit, ordering a new shirt is very easy. You no longer have to rely on brands to come up with the right design for you. You can also buy stuff designed to be tucked in. Image

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More from @dieworkwear

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
Nov 24, 2025
Here is a guide breaking down what goes into quality men's footwear. This is focused on men's shoes, as women's shoes, depending on the style, will have different construction techniques and thus standards. 🧵
First, let's set a standard. What does it mean for a pair of shoes to be "good quality?" In this thread, I define that standard to be two things:

— Do the shoes age well?
— Can they be easily repaired?

In short, you should want and be able to wear the shoes for a long time. Image
We'll start with the part most people see: the uppers.

Quality uppers are made from full grain leather, which shows the natural grain of the hide (pic 1). Low quality uppers will be made from corrected grain, where bad leather has been sanded and given a chemical coating (pic 2) Image
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Read 20 tweets
Nov 23, 2025
When I was on a menswear forum, one of my most controversial opinions was that certain coats look better when they're worn open, while others look better when they're closed.

For instance, which of these two outfits look better to you? 🧵 Image
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If you shop for an overcoat today, there's a good chance you'll land on a single breasted. As suits and sport coats have receded from daily life, the types of outerwear that men historically wore with them have also slowly disappeared. Image
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If you look at the past, men had all sorts of designs to wear over their tailored clothing: polos, Ulsters, Balmacaans, Chesterfields, paletots, wrap coats, etc. They were offered in a wider range of materials: gabardine, camelhair, covert, heavy tweeds, etc. Image
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Read 8 tweets
Nov 22, 2025
The reason why this looks off is bc the coat is built from many layers of material — haircloth, canvas, and padding — which sits on top of another jacket with similar structure. This can make you look a bit like a linebacker. If you find this to be the case, switch to a raglan 🧵
A raglan is defined by its sleeve construction. Most coats have a set-in sleeve, which is to say the sleeve attached to a vertical armhole, much like a shirt. A raglan, by contrast, has a diagonal seam running from the neck to armpit. Historically, this was put on raincoats. Image
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A raglan construction is a bit more waterproof that its set-in sleeve counterpart because there's not vertical seam in which water can sit and eventually penetrate. But most importantly, it's completely devoid of padding. This results in a softer, rounder shoulder line. Compare: Image
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Read 4 tweets

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