derek guy Profile picture
May 12, 2024 8 tweets 4 min read Read on X
I've been toying with different AI programs to see if they can suggest good outfits. They can't. They all fail because they don't understand the cultural language of clothing, so their suggestions are generic. Outfits are no better than clothing subscription boxes; maybe worse.
IMO, AI will replace fashion writers who generate generic advice like this. And just as there's a market for this now, there will be a market for this sort of AI-generated advice. I just don't think it leads to good outfits or improves people's relationships with clothes. Image
People suggesting that this can be improved miss an important point. For this to work, AI has to be able to read your heart (your personality, interests, cultural background, identity, emotions, etc). It has to figure out how you see yourself positioned in culture.
Here is a perfectly fine outfit that looks bad because it's on the wrong person. The outfit does not mesh with the person's "vibe" (or even the room). Image
By contrast, here are four different aesthetics that work for the person underneath the clothes. Each aesthetic is governed by different "rules." There are no real universal rules in fashion; everything is dependent on the aesthetic, which is, in turn, rooted in culture. Image
AI may give you something like this, which may be an improvement over how you dress now. But this is also pretty generic, and lots of people don't look as good as this model in the same clothes. Many also feel unsatisfied in these clothes, so they keep chasing trends. Image
For AI to work, it must understand the cultural language of clothing and read your heart. What do you want to express? What is your cultural identity? What is the culture you're in? Which clothes make you excited? These are not things AI can answer for you.
Image
Image
Example: you're wearing a navy sport coat with tan trousers. Should you wear

— suede tassel loafers to look bookish?
— gator penny loafers to look louche?

This is just within a single niche aesthetic; there are hundreds of other aesthetics. AI can't answer for you: "Who am I?"

Image
Image
Image

• • •

Missing some Tweet in this thread? You can try to force a refresh
 

Keep Current with derek guy

derek guy Profile picture

Stay in touch and get notified when new unrolls are available from this author!

Read all threads

This Thread may be Removed Anytime!

PDF

Twitter may remove this content at anytime! Save it as PDF for later use!

Try unrolling a thread yourself!

how to unroll video
  1. Follow @ThreadReaderApp to mention us!

  2. From a Twitter thread mention us with a keyword "unroll"
@threadreaderapp unroll

Practice here first or read more on our help page!

More from @dieworkwear

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
Image
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
Image
Image
Image
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
Image
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
Image
Image
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
Image
Image
Image
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
Image
Image
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
Image
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
Image
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
Image
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
Image
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
Image
Image
Image
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
Image
Image
Image
Read 8 tweets

Did Thread Reader help you today?

Support us! We are indie developers!


This site is made by just two indie developers on a laptop doing marketing, support and development! Read more about the story.

Become a Premium Member ($3/month or $30/year) and get exclusive features!

Become Premium

Don't want to be a Premium member but still want to support us?

Make a small donation by buying us coffee ($5) or help with server cost ($10)

Donate via Paypal

Or Donate anonymously using crypto!

Ethereum

0xfe58350B80634f60Fa6Dc149a72b4DFbc17D341E copy

Bitcoin

3ATGMxNzCUFzxpMCHL5sWSt4DVtS8UqXpi copy

Thank you for your support!

Follow Us!

:(