How to start a new column in flex column wrap layout

Question

I want my data to be arranged in columns (top to bottom, left to right) and every heading inside the data should start a new column. There are three constraints:

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Answer 1

Apparently, the correct solution is to use the break-before or break-after property:

A break is forced wherever the CSS2.1 page-break-before/page-break-after [CSS21] or the CSS3 break-before/break-after [CSS3-BREAK] properties specify a fragmentation break.

At the time of writing, most browsers implement the *-break-* properties incorrectly or do not implement them at all. Consider this answer ahead of its time.

The following demo works in:

• FF33

.grid {
  display: flex;
  flex-direction: column;
  flex-wrap: wrap;
}
.grid .head {
  width: 25%;
  background: orange;
  border-bottom: thin dotted;
}
.grid .data {
  width: 25%;
  background: yellow;
  border-bottom: thin dotted;
}
/* force column breaks */
.grid .head:nth-child(n + 2) {
  page-break-before: always; /* FF33 */
}

<div class="grid">
  <div class="head">Column 1 (3 items)</div>
  <div class="data">item 1-1</div>
  <div class="data">item 1-2</div>
  <div class="data">item 1-3</div>
  <div class="head">Column 2 (4 items)</div>
  <div class="data">item 2-1</div>
  <div class="data">item 2-2</div>
  <div class="data">item 2-3</div>
  <div class="data">item 2-4</div>
  <div class="head">Column 3 (2 items)</div>
  <div class="data">item 3-1</div>
  <div class="data">item 3-2</div>
  <div class="head">Column 4 (1 items)</div>
  <div class="data">item 4-1</div>
</div>

Chromium Version 73.0.3683.75

Does not respect the column break:

Answer 2

I don't think there is a way to do this with flexbox, however, if we use column-count we can take advantage of the properties:

‘break-before’, ‘break-after’, ‘break-inside’

In particular:

We can set break-before: column; on each 'head' element, where the column value means:

Always force a column break before the generated box.

(similarly if we were using break-after:column this would force a column break after the generated box )

NB: Browser support is currently limited to IE (!!)

.grid {
    columns: 4;
    column-gap: 0;
}

.grid > div {
  background: lightyellow;
  border-bottom: thin dotted;
}

.grid .head {
  background: gold;
  border-bottom: thin dotted;
  break-before: column; /*                                                                      

                                                        
            

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Answer 3

If you can dynamically add a div before each head (except the first), it may be possible. Credits go to Tobias Bjerrome Ahlin. Tested on Chrome, Firefox, Safari and IE11.

.container {
  display: flex;
  flex-wrap: wrap;
  flex-direction: column;
  height: 200px;
}

.item {
  background-color: #A2CBFA;
  border: 1px solid #4390E1;
  margin: 2px;
}

.break {
  flex-basis: 100%;
}

<div class="container">
  <div class="item">item 1</div>
  <div class="item">item 2</div>
  <div class="break"></div>
  <div class="item">item 3</div>
  <div class="item">item 4</div>
  <div class="item">item 5</div>
  <div class="break"></div>
  <div class="item">item 6</div>
  <div class="break"></div>
  <div class="item">item 7</div>
  <div class="item">item 8</div>
</div>