I think there's a third very specific category of "men who care but don't know how, but they love making systems out of things to help solve their problems." You might find one or two of these kinds on Hacker News.

Totally agree & I started in this category so I can sympathize. I spent more $ & time in dressing rooms than I care to admit to figure out what specific outfit combinations worked and how different brands fit. Having something like this that worked well would've been an amazing starting point, and I was hoping that Pinterest's visual search feature would eventually become something like this (as that'd get me to actually use Pinterest). I think more men would dress well if it weren't so hard!

So we just need Garanimals for grown ups?

There's men who care because society cares but don't want to spend all the effort gaining the instincts themselves. Probably also useful for people who come from, for example, poor families and never had guidance on such things growing up so would need to devote extra effort to gain the instincts.

Well, I think what they need is to look at a blog like https://putthison.com/. It’s easier to read a few articles on there than to try to use some janky app everyday.

You must be confused, they said they want to look good...

I for one would love to be well dressed, but I don't know how.

We exist, but it's not something you exactly brag about :)

Read through r/malefashionadvice and their wiki, they have a bunch of info on how to improve your style. Specifically, they have threads every day called What Are You Wearing Today which has people take pictures of themselves and what they're wearing specifically (brands, name of clothing SKU) which you can then pick up to buy if you like it, or find alternatives for it.

https://www.reddit.com/r/malefashionadvice/wiki

Start reading fashion magazines and tear out the pictures of stuff you like. Then when you see something you like at the mall or Macy's, get it. If there's stuff in your closet you don't wear (or don't like to wear), fold it and put it in storage and if you haven't needed it for 6-12 months, give it away and replace it with a garment of the same type that you like.

You can probably get this integrated into some other lower friction point than the phone/browser, such as a smart display or assistant. Could also be useful for shopping to make sure the person actually has the right clothes to make the combos. Problem is, until they crack the combos, there is no product.