Don Draper is a pre-modern urban gentleman. Some of his values would not measure up to today’s standards, and his suits fit him in a hybrid 1960s/2010s kind of way, but he has the clothing and swagger of a gentleman of the time. In fact, his style has been a heavy influence on men’s fashion over the past seven years, even inspiring a recurring collection at Banana Republic.

There is one very subtle detail the modern urban gentleman can and should purloin from Mr. Draper for very little cost indeed: the pocket square.

The pocket square is an all-too-often forgotten accessory to the gentleman’s suit. Many men do not even realize the suit jacket pocket is a pocket; the suit is most often sold with the pocket sewn shut, and it is up to the consumer to take a seam ripper to it. And just like pants with belt loops require a belt, a suit jacket pocket dictates a pocket square.

(Another item to correct for the record right from the start: a pocket square and a handkerchief are not the same thing. The gentleman generally keeps his bodily fluids to himself.)

Much like the necktie, the pocket square is an outlet for personal creativity. That doesn’t mean it comes without guidelines, however. Always remember that each style choice is an extension of the image the wearer wishes to project at that moment in time. That image is reflected in the color, pattern, fold, reveal, and fabric of the pocket square.

Color and pattern

The newly minted gentleman may hear a play-it-safe “rule of thumb”: match the pocket square to the tie. Yes, but no. To match is not to duplicate. The local department store sells a downright atrocity, the tie and pocket square set, that more often than not pushes two lackluster items cut from the same cloth. Just as you wouldn’t wear a denim shirt with jeans of the same wash, this is not what is meant by “matching.” It looks bad even on Beckham.

To match, instead, means to complement. The Modern Urban Gentleman often bases the primary color of his pocket square not on the primary color of the tie, but of the shirt, and matches the accent color of the square to the tie (example 1; example 2ish).

The same don’t-duplicate rule applies to the pattern. Pair a solid tie with a paisley square, or even microdots with polkas. Keep in mind that the shirt color and pattern also factor into the equation. Balance the conservatism of one or two with the flair of the other: If the shirt is a 2 on the flashiness scale and the tie is a 3, the square can be a 7. Don’t be boring, but don’t overwhelm with a mishmash of hues and designs.

Also match the square to the setting. As mentioned above, style is a projection of self. If the gentleman is attending an event where he shan’t speak above a whisper, his clothes should match that volume. Going to the opening of a modern art gallery? Indulge your wildest Etsy fantasies.

The fold

The setting also determines the way a gentleman folds his pocket square. There are any number of online tutorials that teach how to complete any of the many fold options. Explore and learn.

The most conservative and traditional way to fold a pocket square is the Draper-style square fold. The style reflects Draper’s staid manner, and will communicate the same message for any gentleman. Some even place an index card inside the square to give it a crisp, fastidious shape. This fold is a safe bet for a job interview or any other meeting of gravity.

Another traditional fold is favored by Roger Sterling: a square with two, three, even four peaks. Much like Sterling himself, the peaked fold is ostentatious, even a bit affected, and is not endorsed by the Modern Urban Gentleman.

A third option is a modified square fold — a devil-may-care, purposefully messy, but smart-looking choice. Follow the same folding rules as for the crisp square, but intentionally leave the corners and sides uneven to project the same rough-hewn attitude. This fold works best for a heavier material with some texture. The modified square is the Modern Urban Gentleman’s staple fold.

The “puff” fold is also casual, yet more traditional than the modified square. It’s a favorite of Prince Charles, as well as magicians the world over. Lay the pocket square flat, gather fabric from the middle in one hand, and with the other hand, twist and flip the rest of the square up behind the puff. The puff fold looks great in a New Year’s Eve tuxedo and is perfect for laid-back parties. Just be careful to avoid falling into clown territory.

Final details

Once the pocket square is folded, the gentleman must find the right amount of “reveal.” Draper allows the slightest sliver of square to peek above his pocket. The Modern Urban Gentleman advocates about a half an inch in business settings, and up to two inches as the sun sets.

A note on fabric: silk is, as with neckties, the most common fabric of a pocket square. It is also the most formal and should be the exclusive choice of the gentleman in a tuxedo. Linen and cotton pocket squares are also available and are acceptable in less formal situations, so long as they are clearly distinguishable from a handkerchief.

Just five years ago, pocket squares were nigh impossible to find in a store. Thankfully, the tide has shifted. Choose wisely and economically: unlike a suit or even some neckties, a pocket square is not a long-term investment — though it should last quite some time. Spend no more than $40, such as on this Paul Stuart tipped cotton, which will contrast nicely on a dark suit. For the bulk of the gentleman’s pocket square collection, the Modern Urban Gentleman again refers readers to The Knottery ($6 to $18) and The Tie Bar (most $8 to $10).

The key to the pocket square is to hit the right note for the setting. The Modern Urban Gentleman is a member of a martial arts association. One of the senior members of the organization subtly projects his elan in the way he wears his pocket square: Before training, when the situation calls for seriousness and focus, the man arrives with a crisply folded square cloth in his jacket pocket; as he walks out the door at the end of the day, ready to enjoy steak, Scotch, and fellowship, his pocket square is an elegant puff of confidence.

Gentlemen: emulate this man.