Yes,
clear doesn't apply to inline elements. Well, .. it does officially, but because of the way inline elements work it won't have the desired effect.
In the demonstration below the span element won't pop-up above the UL if there isn't enough room for it. Try increasing the width of the DIV to see the effect.
Code:
<!DOCTYPE html>
<html>
<head>
<title>Page Title</title>
<style type="text/css">
.style1 {
width: 100px;
float: left;
outline: 1px solid blue;
}
div {
width: 100px;
}
</style>
</head>
<body>
<div>
<ul class="style1">
<li><input type="checkbox" value="1">Value</li>
<li><input type="checkbox" value="1">Value</li>
</ul>
<span style="clear: both;">Hello</span>
</div>
</body>
</html>
But you don't really want to do this; just use a block-level element (P or DIV).
Added: Actually, the clear:both has no effect on the in-line element. The W3 says
you can apply it to in-line elements but it's ineffectual.