Lately, the rich and restless of Silicon Valley have been appearing more often at the sort of formal events that call for black tie. It has not been going well.

At the Breakthrough Prize ceremony in April, for instance, Sam Altman wore a shrunken dinner jacket with low-rise trousers, which exposed a bit of shirt beneath his coat’s buttoning point, spoiling the line that should define this type of elegant attire. Similarly, Jeff Bezos wore a business vest with a tuxedo to his wedding over the summer, prompting Milanese bespoke tailor Nicoletta Caracenci to lament on Instagram, “[I’m] really suffering.” And at the White House state dinner last month, David Sacks posted a photo of himself alongside Greg Brockman, Elon Musk and Jensen Huang. Sacks and Huang wore long black ties that turned their celebratory outfits into something mournful, Brockman chose dull-black penny loafers, and Musk arrived in balloon-soled sneakers that looked as if they had been inflated with a bicycle pump.