JSFiddle - React, Tailwind, and code Playground

HTML

<div class="item-list">
    <ul>
        <li class="column-1">test</li>
        <li class="column-1">test</li>
        <li class="column-2">test</li>
        <li class="column-2">test</li>
    </ul>
</div>

CSS

.first {
    background:green;
}

JavaScript

//$('div.item-list > ul > li.column-1:first-child,div.item-list > ul > li.column-2:first-child').addClass('first');

$('div.item-list > ul li').closest('.column-1').closest('.column-2').first().addClass('first');
//$('div.item-list > ul li').closest('.column-2').first().addClass('first');