<html>
<head>
<style>
/* 
The aspect-ratio preserving object-fit:cover property causes the 10x100 image to be scaled to 100x1000 and then centered.
The shape-outside is clipped to the image-shape's margin-box, which means that most of the scaled image will be clipped away.
*/
#image-shape {
    float: left;
    -webkit-shape-outside: url("data:image/svg+xml;utf8,<svg xmlns='http://www.w3.org/2000/svg' width='10px' height='100px'><rect width='10' height='100' fill='blue'/></svg>");
    width: 100px;
    height: 200px;
    margin-right: 50px; /* expose shape-outside property failures */
    object-fit: cover;
}

#content {
    font: 50px/1 Ahem, sans-serif;
    -webkit-font-smoothing: antialiased;
    color: green;
}
</style>
<div id="content">
  <img id="image-shape"
    src="data:image/svg+xml;utf8,<svg xmlns='http://www.w3.org/2000/svg' width='10px' height='100px'><rect width='10' height='100' fill='blue'/></svg>">
  </img>
  X<br>X<br>X<br>X<br>X
</div>
</body>
</html>