The three-button jacket
Fashions exist even within classic menswear, and over the decades men have chosen one, two, three and even four-button suits. But generally the most common style has either been a two- or three-button.
At the start of the 21st century, three buttons were more fashionable than they had been in a long time. But it's important to differentiate true three- buttons and three-buttons that ‘roll’.
A true three- button jacket will have lapels that end, abruptly, just above the top of those buttons (see image above). When only the waist button (the middle one of the three) is fastened, this short lapel will create a sharp, awkward angle at the top of the jacket’s front. It has been designed to button the top two, and looks odd if they are both unfastened.
Most other jackets have some amount of 'roll' to them, so that when the top button is unfastened, the lapel rolls back and lengthens, ending somewhere above the waist button. This roll or lack of it is driven by factors such as the canvassing of the chest and the tension of the collar.
High fastenings (which three- or four-buttons naturally demand) look good on fewer people, as they shorten the plunge of the lapel and reduce that uniquely elongating, strengthening effect of a tailored jacket.
Nevertheless the style has been popular in the past when driven by specific fashions, such as the Mods. And they usually inherited parts of their look from earlier gentleman’s attire, where as little shirting was on display as possible – leading to the necessity of a high-fastening jacket or an ever-present waistcoat.
The ‘three-roll-two’ jacket
Often associated with but not exclusive to Italian bespoke tailoring, the ‘three-roll-two’ jacket is not designed to fasten its top button. As shown above, the jacket is only fastened at the middle button so the lapels roll naturally outward.
This is a nice, slightly more relaxed alternative to the button options that follow, and certainly more laid back than the 'true' three-button jacket.
An argument for a second button
So, you may well ask, what is the point of a second button? It seems redundant. Many commentators have shared this view, arguing that one button looks more stylish and three more practical, while a two- button jacket is just dull.
There are three principal reasons for adding the second button.
The first is practical – a little wind can turn your jacket fronts inside out, flapping them around and forcing you to repress them with your hands. Although you wouldn't normally button the lower button, you do have the choice when needed.
The second is a matter of style: one button is sharp, singular, not to say rakish.
Notwithstanding the jacket’s heritage – coming from the morning coat and riding wear – nor its superb modern manifestation (thanks to Huntsman and latterly Richard Anderson), this is a style. And some men don’t want a style – they want normal, they want unobtrusive, they want stolid. They do not want anything that could suggest a rake. For them, the two-button jacket is the most flattering and practical.
Finally, and perhaps least importantly for today’s man and modern style trends, a one-button jacket often looks best with high-waisted trousers.
Back when all men wore braces, their trousers all started around their belly button, so the waist of the trousers and of the jacket were both at the same point.
This meant that when they put their hands in their pockets, pulling apart the jacket, no shirting was on display. While this isn’t necessarily recommended for every modern man, a triangle of puffy shirt is hardly flattering and diminishes the upward-sweeping line of the lapels.
So as a one-button jacket means more of a cutaway front, there is more potential for displaying your waist and shirt in this way. Trousers on the natural waist are not required, but the argument for them strengthens. And few men wear trousers of that height today.
One versus two-button is a matter of personality, but consider the arguments on both sides.