How to Fold a Pocket Square – Mad Men Styles

There are many, many ways to fold a pocket square but don’t be overwhelmed by the variety. There are 85 ways to tie a tie but you probably stick to one, maybe two, classic styles. Here’s how to fold a pocket square, illustrated by the dapper gentleman of Mad Men.


The choice of fold reflects not only the style but the personality of the wearer. Don Draper sticks with a humble flat fold that still let’s his power show throw while the former big bosses Roger Sterling and Bert Cooper opt for more ostentatious and uncommon folds. Their distinctive styles have been immortalized in these posters by Christina Gee. The right choice is up to you but remember, an accessory should add to an outfit but not become the focal point – that should always be you.

The simplest, most common, and Don Draper‘s choice of pocket square is the flat fold. It’s pretty much what it looks like, a square or rectangle (depending on how deep the pocket is) with a 1/4″ visible. While it’s not complicated, this little details adds so much to a suit or tuxedo. When in doubt, go with white. Or for more visual impact, add some stripes, color, or pattern to the mix.

The puff or casual fold is for a less formal look that still impresses. This fold is best suited for patterned pocket squares like paisley, tartan, or polka dots. For more presence, there’s Roger Sterling‘s signature crown fold, also known as “three tips up“. Or go the next step with Bert Cooper‘s distinctive four-fold pocket square. Both work with pattered or solid color pocket squares.

Here’s how to wear a pocket square and check out these easy to follow folding instructions to try out these different folds at home.