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AI And Footwear: Should You Trust AI With Your Shoe Advice?

Is The Future Here?

In today’s article I want to talk about AI and Footwear in what will hopefully become a miniseries.

AI (Artificial Intelligence) and AI-Powered Chatbots have been making leaps and bounds during the last year.

For just 20-25$ (or even using the free version) you can do research, ask for advice and compile lists and recommendations on all topics.

Of course, this extends to shoes and clothing.

But how reliable is it really in early 2024?

Let’s find out.

Can AI Help Me Find My Sizing?

AI and footwear (and clothing) is a combination that will only keep getting more interesting.

Combinations, colors and of course sizing is very important and oftentimes a tedious task for men.

If you asked me to reply simply if “AI can help you find your dress shoe sizing” I would say no, or at least partially yes.

I have been working with dress shoes for 6 years now and I have tremendous knowledge when it comes to sizing different brands.

Different lasts, shapes and feet, people asking for measurements and Brannock devices.

It makes it complicated.

So while AI can browse the web and get some things right, it will often get it wrong.

AI also performs better when you feed it precise information, so every word matters.

Let’s look at some case studies I did myself.

1. What is My Carlos Santos 401 Sizing?

My first question was simple.

Give me sizing advice on carlos santos 401 last. I wear usually UK 8 (US 9D) Dress Shoes.

AI and Footwear
What is my Carlos Santos 401 Dress Shoe Size – AI Answers

Very interestingly (and smartly), it browsed the web and retrieved information from Misiu Academy and The Noble Shoe.

These are all articles and tips I wrote myself, so in this case they are bound to be correct.

For 99% of the people with a regular width foot, last 401 of Carlos Santos will run large.

It is important to note that AI will always tell you to consult with the retailer or manufacturer.

2. What is My Size on Carlos Santos & Other Brands

Here, we approach the same question but asking without too much of a sentence structure, feeding basic information.

I usually wear UK 8 (US 9D Dress Shoes). What is my size on Carlos Santos, Carmina, Edward Green, Allen Edmonds?

Notice the reply.

Second Question - AI and Footwear
Second Question – AI and Footwear

In the first response, it gets it right because it is quite simple.

The same applies to number 4, because they tend to run quite standard for most things.

For Carmina though, it states that they fit similar to Carlos Santos which is not correct.

You should size down half for all Carlos Santos lasts but 389/462/453 for example compared to the Rain and Forest.

Simpson on the other hand is a narrow last that needs half a size up.

In this example, a UK 8 would choose:

  • Carlos Santos UK 7.5 (Lasts 316, 397, 445, 401, 387, 234, 362)
  • Carlos Santos UK 8 (Lasts 389/462)
  • Carmina UK 8 (Forest, Rain)
  • Carmina UK 8.5 (Simpson)

This is exactly why you need to be more wary.

In number 3, it is very confused as it repeats Edward Green, asks you to size down from G&G and compares it to Carlos Santos.

If everything was phrased very clearly and with much detail, it probably would’ve been much more accurate.

ChatGPT also uses Bing as a search engine which is utter rubbish.

3. List Me The 10 Best Dress Shoe Brands

The next question is one that is funny and we can compare to my infamously popular Best/Worst Dress Shoes.

List me the 10 best high quality, luxury leather dress shoe brands for men that are Goodyear Welted or Hand-Welted.

Here’s the reply.

It found a website I never heard of before and listed what it found there.

Best Brands - AI and Footwear
Best Brands – AI and Footwear

Most brands are correct, but this is clearly an affiliate marketing website with links and commissions.

Church’s would never be in this list and some of them are contentious if you are a connoisseur.

If you ask the same question but ask to include multiple sources, it becomes a little better but I would still not recommend it.

4. Don’t Let it Draw For You!

Basic AI available to the public is notoriously bad when it comes to drawing certain elements.

It cannot generate belts, loops, fingers and other things correctly.

When I asked it to “Draw me a classic high quality dress shoe appropriate for formal wear” it came up with a hideous shoe for example.

Oxford lol
AI generated Oxford of some short

At least it was an oxford?

Thinking about it, it’s not such a bad attempt but it is something you should not rely on if you are looking for new shoes.

Reach out to reputable bloggers, retailers, ask for advice from real people instead.

5. List of 5 Dress Shoes

We already know there’s no such thing as a “Best X List” since it varies a lot and is highly controversial.

Nonetheless, when asking ChatGPT to show me 5 Dress Shoes that are important for someone that is starting from scratch I got a basic answer.

Oxford, Derby, Monk Strap, Brown Brogues and Loafers.

Given that Brogues fall into many categories and there are no Chukkas or Chelsea Boots in there, I consider it a bust.

Asking for a specific model and brand for each gave another answer which is generally laughable.

  • Allen Edmonds Park Avenue: Popular answer, not bad on deep sale and accessible to the USA.
  • Loake Aldwych Mahogany: Not a bad start, though you can do better
  • Clarks: There’s nothing to say about them, they are garbage
  • Magnanni: Magnanni is not worth your money
  • G.H. Bass & Co. Weejuns: I don’t have to comment here either

Since I gave it no budget, I expected to find expensive great shoes like Yohei Fukuda, Meccariello, Bemer, Carmina, Yeossal and the list goes on.

Of course, it browses the web for popular websites such as GQ and others and this is the result.

So What’s The Verdict?

I hope you enjoyed this little analysis of a topic not often tackled by many on AI and Footwear.

In its core, AI is still in its infancy, yet it’s still mighty impressive what it can achieve.

You should not rely on it and it is definitely not the way to go about researching dress shoe brands or asking for sizing advice.

If you do delve in this ecosystem, make sure to write very detailed, well-structured questions.

Despite that, always reach out to actual knowledgeable humans with expertise that can assist you further.

If you enjoyed this article and would like to see more, let me know in the comments!

Thank you for reading,

Kostas Mandilaris,
Misiu Academy


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