CSS to line break before/after a particular `inline-block` item

When rewriting the html is allowed, you can nest <ul>s within the <ul> and just let the inner <li>s display as inline-block. This would also semantically make sense IMHO, as the grouping also is reflected within the html.

<ul>
    <li>
        <ul>
            <li>Item 1</li>
            <li>Item 2</li>
            <li>Item 3</li>
        </ul>
    </li>
    <li>
        <ul>
            <li>Item 4</li>
            <li>Item 5</li>
            <li>Item 6</li>
        </ul>
    </li>
</ul>

li li { display:inline-block; }

Demo

$(function() { $('img').attr('src', 'http://phrogz.net/tmp/alphaball.png'); });

h3 {
  border-bottom: 1px solid #ccc;
  font-family: sans-serif;
  font-weight: bold;
}
ul {
  margin: 0.5em auto;
  list-style-type: none;
}
li li {
  text-align: center;
  display: inline-block;
  padding: 0.1em 1em;
}
img {
  width: 64px;
  display: block;
  margin: 0 auto;
}

<script src="https://ajax.googleapis.com/ajax/libs/jquery/1.11.1/jquery.min.js"></script>
<h3>Features</h3>
<ul>
  <li>
    <ul>
      <li><img />Smells Good</li>
      <li><img />Tastes Great</li>
      <li><img />Delicious</li>
    </ul>
  </li>
  <li>
    <ul>
      <li><img />Wholesome</li>
      <li><img />Eats Children</li>
      <li><img />Yo' Mama</li>
    </ul>
  </li>
</ul>

You are not interested in a lot of "solutions" to your problem. I do not think there really is a good way to do what you want to do. Anything you insert using :after and content has exactly the same syntactic and semantic validity it would have done if you had just written it in there yourself.

The tools CSS provide work. You should just float the lis and then clear: left when you want to start a new line, as you have mentioned:

See an example: http://jsfiddle.net/marcuswhybrow/YMN7U/5/

I've been able to make it work on inline LI elements. Unfortunately, it does not work if the LI elements are inline-block:

Live demo: http://jsfiddle.net/dWkdp/

Or the cliff notes version:

li { 
     display: inline; 
}
li:nth-child(3):after { 
     content: "\A";
     white-space: pre; 
}

An easy way to split lists into rows is by floating the individual list items and then the item that you want to go to the next line you can clear the float.

for example

<li style="float: left; display: inline-block"></li>
<li style="float: left; display: inline-block"></li>
<li style="float: left; display: inline-block"></li>

<li style="float: left; display: inline-block; clear: both"></li> --- this will start on a new line
<li style="float: left; display: inline-block"></li>
<li style="float: left; display: inline-block"></li>