derek guy Profile picture
Aug 5, 2025 10 tweets 6 min read Read on X
I disagree. I will tell you what's wrong with his jeans. 🧵
Let's start with an experiment. Here are two men wearing tailored jackets with jeans.

Which do you think looks better? Image
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If you choose the outfit on the right, then we have the same taste. But why does he look better?

The answer stems fro a basic rule of classic tailoring: the jacket needs to have a certain relationship with the trousers so as to form a harmonious whole. Image
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This means the jacket's line has to flow into the trousers. And the trouser rise has to be high enough to hide the shirt that would otherwise peek below the jacket's buttoning point, disrupting the line. See how the outfit on the left is more harmonious than the right. Image
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The problem is that jeans aren't cut like trousers — and they shouldn't be, as that will make them look weird. Jeans are commonly lower in the rise and smaller through the fork. They are also typically a bit slimmer through the leg. This results in a different silhouette. Image
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This distinction can really disrupt a tailored outfit. On the left, we see how low rise, tapered trousers exacerbate the worst of this look (orphaned suit jacket with jeans, which looks like a sartorial mullet). The outfit on the right is even worse, as the man looks like Gru. Image
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There's a rich history of men wearing tailored jackets, but when they're successful, you'll notice a theme: the jacket is casual (a sport coat, not a suit jacket) and often made from textured materials like tweed. The jeans are slightly higher in the rise and fuller in the leg. Image
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Low-rise jeans have to be styled differently. There are many groups who have worn them stylishly in the past, so you have to find the original images to understand their cultural language. Those groups don't include people who wear classically cut sport coats. Image
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If you're looking for jeans you can wear with sport coats, consider Buck Mason's Full Saddle cut, Levi's Vintage Clothing's 1947 501s, Rubato Lot Nr1, Orslow 105 and 107, and The Armoury by Nigel Cabourn. Todd Shelton can also make custom jeans if you can't find what you need. Image
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wtf a military drone just flew over me?? Image

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More from @dieworkwear

Apr 15
Someone asked if I could tell them where to buy a pair of good chinos. In this thread, I will tell you, but my answer is not simple. On the upside, I think this is a better approach when shopping for clothes and you can apply it to any kind of item. 🧵 Image
A simple answer will go something like this: "Such-and-such makes the highest quality chinos." Or "this brand provides the best value." While potentially useful in some respects, I don't think this gives you the fullest picture.

Instead, let's start at the beginning.
During the 1898 Spanish-American War, US troops stationed in the Philippines wore sand-colored pants made from a heavy cotton twill woven in China. Since the Philippines had been under Spanish colonial rule at this time, the locals call these "pantalones chinos" (Chinese pants). Image
Read 23 tweets
Apr 4
One day, "It" will happen, by which I mean sudden and unexpected news that you want to celebrate. In such cases, you will want the right outfit. 🧵
What do I mean by "It?" I mean that joyous moments are not always something you can plan for. Perhaps you received a pay raise or got accepted at a waitlisted school. Perhaps a loved one is now cancer-free. Such moments can be sudden and unexpected — and you want to be prepared. Image
Of course, you can always celebrate in the same clothes you wear to bed. But IMO, this diminishes the moment. Thus, it's nice to special outfits for "It," even if you don't wear them all the time. It's similar to toasting a special glass of champagne and drinking water. Image
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Read 14 tweets
Mar 21
In the 1950s, Irving Penn traveled across London, Paris, and NYC to take portraits of workers in their work clothes. These clothes at the time were not considered glamorous — they would not have shown up on fashion runways — but they demonstrate a simple aesthetic principle 🧵 Image
Consider these outfits. How do you feel about them? Are they charming? Repulsive? Stylish?

If you consider them charming and stylish, as I do, then ask yourself: what makes them charming and stylish? Why are you drawn to the outfits? Image
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As I've mentioned before, I think outfits look better when they have "shape and drape." By shape, I mean the outfit confers a distinctive silhouette. If these men took off their clothes, we can reliably guess their bodies would not be shaped like this: Image
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Read 14 tweets
Feb 20
Let me show you a wardrobe you can build with $1,700 🧵
NAVY SPORT COAT

If you're just dipping your toes into tailored clothing, start with a navy sport coat. This is something you can wear with a button-up shirt and pair of trousers, or something as casual as a t-shirt and some jeans. It's easily the most versatile jacket. Image
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Key is to get something with texture so it doesn't look like an orphaned suit jacket. Spier & Mackay has great semi-affordable tailoring. Their navy hopsack Moro is made from pure wool and a half-canvas to give it shape. Classic proportions and soft natural shoulder

Price: $358 Image
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Read 16 tweets
Feb 16
There's a pervasive belief that we no longer produce clothes in the United States. This is not true. In this thread, I will tell you about some great made-in-USA brands — some that run their own factories, while others are US brands contracting with US factories. 🧵 Image
I should first note this thread focuses on well-made, stylish clothes produced in ethical conditions. For me, producing in the US is not enough. It means nothing if the clothes are ugly, crappy, or produced in sweatshop conditions. My article for The Nation below. Image
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JEANS

Gustin produces MiUSA jeans using raw Japanese denim. "Raw" means the fabric hasn't been pre-distressed, allowing it to naturally fade with use, reflecting your actual body and lifestyle. I like their fuller 1968 Vintage Straight fit. They also do lots of other stuff. Image
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Read 17 tweets
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

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