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 corporate and 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 — or too intimidated to ever dream of betraying his client.
In the case of a villainous character (usually the Big Bad, though not always), this can also be used to show how evil he is (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.
- In an E-Trade advertisement, the E-Trade baby does this, talking to the audience while Enzo takes his measurements.
- Walter from The Mask gets fitted for a new suit to signify his ascendance to the role of proper Big Bad. It also helps show off just how huge he is.◊
- Turned into comic relief during the JMS run of Spider-Man. New nemesis Morlun was introduced with lots of grim foreshadowing about how evil and powerful he was. That's exactly what the narrative captions were talking about while the art showed him having a suit fitted. Morlun's dialogue, though, was focused on whether or not the new outfit made his butt look big.
- 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 Porter taken care of.
- In The Tourist, Reginald Shaw has a Mob Boss Suit Fitting, even insisting that the tailor remain when his mooks arrive. He takes a report from his cronies and uses the tailor's measuring tape to strangle one of them when he makes a mistake. Only at the end of the scene does he comment to the tailor, mentioning that the suit fits him very nicely.
- A variation in The Untouchables (1987), with Al Capone talking business while getting a straight-razor shave from a barber.
- Played for Laughs in the Louis de Funès movie The Wing or the Thigh, where the temperamental director of a restaurant guide is dictating a review of an establishment while a tailor is taking his measurements for a new suit. Of course, as he walks along dictating, he drags the poor tailor all around the office.
- Primo Sindone is seen getting a suit fitted in Analyze This. The discussion he has with his underling starts out mundane (wanting to see a movie but there's nothing good on) before turning to the movie's plot.
- James Cagney in The Public Enemy may be the Trope Maker (although the tailors taking measurements, rather than Powers and his accompanying mook, discuss a certain recent liquor warehouse heist).
- How to Succeed in Evil (the novel for sure, probably the podcast too) features, actually, many of these. Edwin Windsor's tailor is not just such a consummate discrete professional that a consulting supervillain can talk freely in front of him, he's actually one of his closest and most dependable cronies. Edwin's favored mode of re-centering himself and rebuilding his morale after any big setback is by having a new suit fitted.
- Played with on Star Trek: Deep Space Nine, in the season 4 premier "Way Of The Warrior". Captain Sisko calls Garaknote in for a fitting while he's having a staff meeting concerning the Klingons' plans to invade Cardassia. Garak is even mindful enough to ask Sisko if he's sure he doesn't want him to come back after the meeting instead of taking Sisko's measurements now.
- 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.
- Daredevil: Wilson Fisk has his suits personally tailored for him by Melvin Potter, who designs them to be knife and bullet resistant. He even loans Melvin's services to Leland Owlsley after Leland gets threatened by Matt Murdock. Matt eventually finds out about Melvin and gets him to build him similar body armor, and becomes his main gear supplier by the start of season 2. Midway through season 3, Melvin is later forced by Fisk to build an identical Daredevil suit for Benjamin "Dex" Poindexter.
- Robin of Sherwood: The Sheriff in "Herne's Son", looking over new robes from his tailor while extorting gold from Sir Richard.
- "Pax Soprana", a first season episode of The Sopranos, shows Corrado "Junior" Soprano, newly designated head of the DiMeo crime family of New Jersey, being fitted for a new suit. His tailor tells "Uncle Junior" that the tailor's grandson recently committed suicide due to drugs sold to him by a member of the Soprano crew. Junior promptly has the dealer killed.
- In the Charmed episode "The Wedding from Hell," one scene is about a demonic being (alias Jade DeMon) having her wedding dress fitted by a tailor.
- Hitman: Tommy Clemenza's clothing store. Tom keeps 47's old outfits and a weapon or two in the back room.
- This Robot Chicken spoof of Star Wars has Emperor Palpatine flipping out at Darth Vader over the phone for losing the Millennium Falcon, only for Alphonso the barber to cheerfully suggest hiring a bounty hunter.
Palpatine: (hangs up) I just want to sit in a hot bath and cry!
Alphonso: You're looking for some guys? What about a bounty hunter? You know, a guy who looks for a guy for money! My sister's dating one!
Palpatine: Alphonso, you're a lifesaver!!!