Mob Boss Suit Fitting

Related to Badass in a Nice Suit, Man of Wealth and Taste, and Sharp-Dressed Man - those suits have to come from somewhere. This is a scene where the boss is conducting his regular business while a tailor is taking his measurements for a new suit. Most frequent in mafia stories, though also common in political thrillers.

This can be done as an Establishing Character Moment to depict a character as clearly being the boss, as it implies he's very comfortable with the idea of the other characters as his subordinates. Bonus points if he talks freely around his tailor about things that should be kept secret, as this shows the tailor himself may also be a subordinate.

In the case of a villainous character (usually the Big Bad, though not always), this can also be used to show he is a Complete Monster (or at least a Corrupt Corporate Executive), ordering out atrocities with mundane nonchalance to show that these are his routine operations. The likelihood of the tailor surviving this encounter is inversely proportional to how nervous he seems while accomplishing his task.

In the case of a character who is on the hero's side, the amount of interaction between the boss and the tailor will reveal much about the nature of the boss.

The boss pays more attention to the tailor's work (usually in a negative fashion) than the business at hand: almost always a case of Obstructive Bureaucrat.
The boss pays absolutely no attention to the tailor, merely complying with the necessity of standing still and moving as needed: usually a sign of Badass in a Nice Suit, and the sign of a Reasonable Authority Figure.

Note that simply having a scene where a character is fitted for a suit does not qualify for this trope. This trope is when a suit fitting is happening while the character is in some way conducting his business. As such, it's something of a subversion of Villains Out Shopping; this villain doesn't see a shopping trip as any reason to put his work aside.

Examples of Mob Boss Suit Fitting include:

Advertising

In an E-Trade advertisement, the E-Trade baby does this, talking to the audience while Enzo takes his measurements, as shown here.

Film

There's a scene in Snatch where Frankie Four Fingers talks with his boss Avi while being fitted for a suit in London. Played more for comedy than anything else, because Frankie is an underling rather than a boss, and some of the suits he is trying on are both a bit outdated and will change very quickly between takes. (For example, he'll be fully in a suit for one take, then a couple of seconds later he'll be half dressed in another, totally different suit from a different era).
In Payback, Carter, one of the Co-Dragons for the Big Bad who is presented as running the city where the story takes place, is seen putting on a suit as he gives orders about how he wants Villain Protagonist Porter taken care of.

Live-Action TV

Played with: there was an episode of Star Trek: Deep Space Nine where Sisko calls Garak in for a fitting while he's having a staff meeting. This is so he can unofficially pass some information to Garak about a planned invasion of Garak's homeworld.
I'm almost positive Lex Luthor has been shown in this kind of scene.^{[please verify]}
The Cape had a scene with Peter Fleming and Scales meeting at a tailor to discuss business. Although Scales is just there to talk, Fleming insists on buying him a suit as well.

Radio

The "political" version was Played for Laughs on a radio episode of Royal Canadian Air Farce, when then-Prime Minister Brian Mulroney was being fitted for a suit while discussing the upcoming federal budget with the Minister of Finance. Both men were asking Mulroney questions; his answers were to both at once and resulted in a very dapper suit and a very unpopular budget... which Mulroney could then avoid the blame for by saying he was talking to his tailor.