How can I make a display:flex container expand horizontally with its wrapped contents?

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It’s curious that most browsers haven’t implemented column flex containers correctly, but the support for writing modes is reasonably good.

Therefore, you can use a row flex container with a vertical writing mode. This will swap the block direction with the inline direction, and thus the flex items will flow vertically. Then you only need to restore the horizontal writing mode inside the flex items.

.container {
  display: inline-flex;
  writing-mode: vertical-lr;
  flex-wrap: wrap;
  align-content: flex-start;
  height: 350px;
  background: blue;
}
.photo {
  writing-mode: horizontal-tb;
  width: 150px;
  height: 100px;
  background: red;
  margin: 2px;
}
<div class="container">
  <div class="photo">1</div>
  <div class="photo">2</div>
  <div class="photo">3</div>
  <div class="photo">4</div>
  <div class="photo">5</div>
  <div class="photo">6</div>
  <div class="photo">7</div>
  <div class="photo">8</div>
  <div class="photo">9</div>
</div>

This approach may have its own bugs in edge cases, especially if you mix advanced layout techniques like floats and nested flexboxs. But for most cases it seems to work properly.

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