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I love the fact the ElementaryOS is so high on the list. I am a happy user
Well... the list is alphabetical.
When someone comes to me and asks how to improve their knowledge of front-end or interaction design, I always recommend reading through these guides.

Why? Companies like Apple, Google, and Microsoft have put a ton of work into identifying usable patterns which have become convention across platforms.

If you want to be a better designer or front-end engineer, take advantage of the work these companies and organizations have done by identifying and sharing these guidelines!

I certainly appreciate learning from history rather than repeating mistakes --- Understanding the change over time lets you at least identify why some things worked and some things didn't. This allows you to make new work more easily and more completely.
Not sure how he overlooked: https://material.io/
I remember we were like 70% of the way done with a big product (already in use/sold) following Material Design patterns.

A new designer joined the team and was very upset because "Google is not known for good design. Apple is."

The Win32 counterpart to the UWP-centric design guidelines are here[1], titled "The Windows Interface Guidelines — A Guide for Designing Software".

Much more practical to designing native desktop software, whether you are using Win32/WinForms/QT or otherwise for your rendering engine. IMHO this is what makes a program 'intuitive' and 'natural' to many working adults ages 25+, which is often the target demographic, even if the program will not look 'modern' or have high "design award" value.

EDIT: and is even available in dead tree form: [2]

[1] https://www.ics.uci.edu/~kobsa/courses/ICS104/course-notes/M...

[2] https://www.amazon.com/Microsoft-Windows-Experience-Professi...

The reason, in my opinion, that the patterns outlined here for Win95 are really nice is that they assume the user knows how to do very little.
So much focus on apps and (web) SaaS products these days, that even Microsoft has recent guidelines only for (simpler) Windows apps it seems. For more complex (Windows desktop) applications I prefer the older guidelines, as https://docs.microsoft.com/en-us/windows/win32/uxguide/how-t...

This one is even older (and outdated), but good to add to the archive: https://docs.microsoft.com/en-us/previous-versions/ms997506(...

Looks like sibling post (https://news.ycombinator.com/item?id=26030070) has an older guide as well. Have you used that one / could you comment on which one of these older guides has the biggest ROI?
Actually haven't used that one, it's even older it seems. Just got it to compare, so can't tell you yet which one to recommend.
For something about HCI why is the font so ridiculously oversized? Very hard to read.
I don't get this either. It's a weird trend and goes against some fundamental rules. There is a text width and font size that is comfortably readable. It's essentially a bug!
Two examples worth mentioning...

Inductive User Interface

Long before Electron became popular, Microsoft explored the idea of creating desktop apps with screens that mimicked the look-and-feel of web pages. An example of this was Microsoft Money 2000 (yes, that's how old is the idea of creating apps with a web-like interface).

Microsoft called it 'Inductive User Interface', and you can still find the documentation for this type of desktop app design on their website:

https://docs.microsoft.com/en-us/windows/win32/appuistart/in...

Windows Phone design language: Metro

This video presentation (from 2010) explains the design principles behind Windows Phone 7.

I've long felt that Windows Phone was the best thing that Microsoft ever designed (heavily influenced by Zune). The visual design and interaction design made for a refreshing change from Android and iOS:

https://channel9.msdn.com/Blogs/Jaime+Rodriguez/Windows-Phon...