The reason a block box appears to wrap when its previous sibling is a float with 100% width is because it's not actually the box that's wrapping, it's its inline content that's wrapping.
The reason this doesn't happen with a flex container is because floats cannot intrude into flex formatting contexts. In fact, the same thing happens with block formatting contexts — if you apply overflow: auto
or overflow: hidden
to the following sibling without display: flex
the following sibling will seem to disappear altogether. (This implies that the first paragraph is true only when the block box does not establish a block formatting context.)
Since your float is 100% width, the flex container's (auto) width is reduced to 0. Its inline descendants don't wrap underneath the float, because those inline descendants are participating in an inline formatting context that's within an anonymous flex item, which itself doesn't wrap since it's the only flex item in the flex container. This flex item is overflowing the flex container; however the flex container itself doesn't overflow the containing block since its used width is 0, allowing it to sit next to the float.
The reason the flex container will wrap if it is display: inline-flex
instead of display: flex
is because an inline-level flex container behaves just like any other inline-level content, wrapping around a float. In this case, it's the flex container itself that wraps — its inline content is still formatted as an anonymous flex item, because flex layout is identical regardless of whether the flex container itself is inline-level or block-level.