
This assumes you meant typeset length (and that all the items are single line)
\documentclass{article}
\def\Itemize{\vbox\bgroup
\let\item\ItemizeItem
\let\endItemizeItem\relax}
\def\ItemizeItem{%
\endItemizeItem
\let\endItemizeItem\xendItemizeItem
\setbox0\hbox\bgroup\strut\ignorespaces}
\def\endItemize{\endItemizeItem\egroup}
\def\xendItemizeItem{%
\unskip\egroup
\setbox4\vbox{}%
\loop
\unskip
\setbox2\lastbox
\ifdim\wd2>\wd0
\setbox4\vbox{\box2\unvbox4}%
\repeat
\nointerlineskip
\box2
\nointerlineskip
\box0
\unvbox4}
\begin{document}
\begin{Itemize}
\item a
\item aaaaaa
\item aaaa
\item aaa
\item aaaaa
\item aa
\end{Itemize}
\end{document}
\itemmarkup (which makes it harder as the items are not explicit arguments of anything, and what do you mean by "length" characters in the input or typeset length isWlonger than..or not? – David Carlisle Feb 22 at 0:01