O'Shea is obviously going for a more fashion forward crowd. For guys who like that kind of stuff, you have to admit it's also a little derivative. Like "hey metal iconography is really hot in fashion right now, let's do an ad campaign with Metallica." The last collection looks like it was inspired by pimps from a bad '90s film, which also falls into this whole "low brow/ low fashion" aesthetic that's really popular with Vetements, Gosha, Hedi SLP, etc. Is that really to be celebrated? Not just in terms of following the crowd, but even just that whole shift in general?
This all seems like a huge gamble.
First, Brioni is first and foremost a tailored clothing company. And the market they're going after doesn't really wear tailored clothing (traditional or otherwise). Even O'Shea himself is rarely pictured in a tailored jacket, and he looks like he's the company model right now for the sort of customer they're after.
Second, if they're able to sell tailored clothing to a more fashion forward audience, how long can that last? And what happens when that crowd leaves that for the next trend? Unlike all the other companies they're competing with, they have less aesthetic mobility (unless they're really just going to become a design house).
Third, why hire O'Shea? Whether you support the fashion forward shift or not, he seems like a weird pick. He doesn't have the design chops or vision to be truly exciting to anyone interested in fashion. And his taste is going to be considered awful for anyone with more traditional sensibilities. Brioni presumably has a huge budget; why couldn't they have gone with a stronger creative director? Is it just because O'Shea, as a person, is more likely to generate press?