- 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.
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- In an E-Trade advertisement, the E-Trade baby does this, talking to the audience while Enzo takes his measurements.
Films — Live-Action
- 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anything else, because Frankie is an underling rather than a boss, and some of the suits he is trying on are both a bit outdated and will change very quickly between takes.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, with Al Capone talking business while getting a straight-razor shave from a barber.
- Played for Laughs in the Louis de Funès movie L'Aile ou la Cuisse, 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.
- 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 buisness. Although Scales is just there to talk, Fleming insists on buying him a suit as well.
- In Daredevil, Wilson Fisk introduces Leland Owlsley to his tailor Melvin Potter. Fisk himself doesn't need a fitting, of course, because Melvin already makes all of his suits and knows his measurements. The scene is used more to introduce Melvin, as he's the source of all of Fisk's knife- and bullet-resistant clothing. Melvin later supplies Matt Murdock with similar body armor, and becomes his main gear supplier by the start of season 2.
- Robin of Sherwood: The Sheriff in "Herne's Son", looking over new robes from his tailor while extorting gold from Sir Richard.
- 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!!!