As always the holy docs hold the solution!

From the Book of I/O Operators:

If what the angle brackets contain is a simple scalar variable (e.g., <$foo>), then that variable contains the name of the filehandle to input from, or its typeglob, or a reference to the same. For example:

    $fh = \*STDIN;
    $line = <$fh>;
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If what's within the angle brackets is neither a filehandle nor a simple scalar variable containing a filehandle name, typeglob, or typeglob reference, it is interpreted as a filename pattern to be globbed, and either a list of filenames or the next filename in the list is returned, depending on context. This distinction is determined on syntactic grounds alone. That means <$x> is always a readline() from an indirect handle, but <$hash{key}> is always a glob(). That's because $x is a simple scalar variable, but $hash{key} is not--it's a hash element. Even <$x > (note the extra space) is treated as glob("$x ") , not readline($x).

So there is no guessing or DWIM involved: it is actually a very simple rule.