The nice thing about Win32 is that it does not try to talk you out of any of this. It just gives you the messages, the handles, the drawing APIs, and enough rope to ...

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A nostalgic deep-dive into Win32 API programming, specifically how to create non-rectangular windows using region objects (HRGN), bitmap-driven shapes, and layered windows with per-pixel alpha. Three working C examples are provided: an elliptical window, a bitmap-shaped window using magenta as a transparency key, and an animated desktop mascot using WS_EX_LAYERED and UpdateLayeredWindow. The post also reflects on why custom-shaped windows largely disappeared — the effort of reimplementing all default window behaviors (dragging, resizing, hit testing, DPI) is high, and desktop UI culture shifted toward reliability over visual novelty.

Direct Win32 API, Weird-Shaped Windows, and Why They Mostly Disappeared