derek guy Profile picture
Dec 22, 2023 11 tweets 8 min read Read on X
Something I dislike about all these "how to improve your wardrobe" articles is that they give you a generic cookie-cutter shopping list. This is a terrible way to build a wardrobe because it just swaps out one generic thing for another. It's much better to: 🧵

sfstandard.com/2023/12/20/san…
1. Develop an eye for what fits

A lot of people confuse "fit" with "silhouette." Just because something is baggy doesn't mean it doesn't fit. "Fit" is much more useful when it's narrowly defined, such as collar gaps, pulling at the waist, hip pockets that flare, etc.
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2. Think About Silhouettes

Think of clothing as shapes, and figure out what kind of shapes you want to wear on your body. There are lots of possible shapes: carrot-cut trousers, straight trousers, rounded tops, elongating coats, wide shoulders, etc.

🔗: tinyurl.com/35yx8dmn



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3. Think of Clothing as a Cultural Language

Don't just combine random things. Think of what your outfit conveys in terms of cultural language. Do you like traditional tailoring, workwear, minimalism, maximalism, or avant-garde? What cultural histories do these draw from?

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When you think of clothing as a cultural language, it's much easier to figure out what to wear. For example, my friend @Barima_ON wears wild colors. But it's not just a mish-mash of random stuff. It draws from eras like the London peacock revolution. Outfit has cultural meaning
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In the original article, they have you swap one generic outfit for another generic outfit. In five years, they'll tell you to switch it again. You may not end up liking the clothes because: 1) they may not fit or flatter; 2) they may not feel like "you."


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Guys never look stylish when they do this because it just looks like they bought their wardrobe through a clothing subscription service. Here's Colbert in a sleek bomber, luxurious joggers, and minimalist sneakers. The outfit doesn't fit his "vibe." Image
Finding your aesthetic requires some experimentation, but it's not just buying into a cookie-cutter shopping list. Here are four great outfits with very different vibes/ aesthetics, but they all look great because they fit the person. Image
Years ago, I interviewed Keri Langerman, a costume designer who worked on Moonrise Kingdom. IMO, it helps to think like a costume designer, as they understand the communicative power of clothing. She gave some tips on how to do this here:

🔗: tinyurl.com/mrxjnub2
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This can all sound very daunting, as it's like learning a new language. But it's better than going on this endless cycle of updating your wardrobe with clothes you don't love. Some other useful articles:

🔗 Some things that can help you get started: tinyurl.com/3pt3s83t
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🔗 How to develop good taste:

🔗 How to judge quality in clothing:

🔗 How to think about color:

🔗 A guide on how to get started:

🔗 Other useful posts: tinyurl.com/mt6jhs6c
tinyurl.com/yc424cbx
tinyurl.com/46pvm37f
tinyurl.com/4b59x9tm
tinyurl.com/57etzujv
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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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