derek guy Profile picture
Apr 5, 2024 12 tweets 7 min read Read on X
Style Lessons from George Costanza

In this thread, I will talk about some dos and don'ts of men's tailoring using one of my favorite style icons, George Costanza. 🧵Image
1. Don't wear suit jackets by themselves

If you do, make sure the jacket can convincingly pass as a sport coat. DeSantis' is obvs wearing a suit jacket bc the fabric is smooth and shiny. George is wearing a slightly textured jacket with brass buttons (making it a blazer).Image
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2. Formal suits should be worn with ties

By formal suit, I mean something you'd wear to a business meeting. Navy or grey, made from a smooth, sometimes shiny wool. These really benefit from having a bit of decoration between the jacket's front edges.Image
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3. Always tuck in your shirt

Casual outfits can go either way, depending on the outfit and the shirt. But outfits that involve traditional tailoring don't look right with an untucked shirt, even in casual iterations such as with chinos or jeans.Image
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4. Don't wear jackets that are too tight

A lot of guys nowadays are wearing jackets that are too small for them. You can check this in a few ways. First, see if you can comfortably fasten the coat. Second, see if you can comfortably hug someone. Should have room for movement.Image
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5. Beware of low-rise trousers

Low-rise pants can work in some aesthetics, but they are rarely good for tailoring. This is partly because you never want your shirt to show beneath the coat's buttoning point when your coat is fastened. Consider high-rise pants—trust me.Image
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6. Don't wear shirts that are too slim

Again, there should be room for movement. An easy way to see if your shirt is too small is to look for lines where the fabric is pulling, especially across the placket. George's shirt here is perfect.Image
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7. Dark top; light bottom

While not a hard rule, you will have more success if you buy dark jackets and light pants. Black or charcoal trousers can be hard to wear in a classic tailored look. Stick to trousers in light grey, mid-gray, and tan, then jackets in brown and navyImage
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8. Beware of collar gaps

A tailored jacket's collar should always hug your neck, even when you're moving. When shopping, if you see the collar lifting off your neck, move on.Image
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9. Check for balance

When trying on a jacket, check to see if the jacket hangs evenly from front to back. Tailors call this "balance." The front can be lower or level with the back, but it should never be higher than the back. This can be a challenge for barrel-chested guys.Image
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10. Don't wear black dress shirts

Especially in dressy materials like a very smooth poplin. If you want to wear a black button-up, try a casual material like a black denim Western shirt or needlecord. Or better yet, a knit like George here. It's more tasteful.Image
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If you enjoyed these looks, it's perhaps worth pointing out that they appeared on television nearly thirty years ago. The fact that George Costanza remains a style icon is a testament to the timelessness of these guidelines. Ignore them at your peril. 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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