Gradually, brands at all levels of the markets got in on the game, including Allen Edmonds and Wolf & Shepherd, and luxury labels like Tom Ford, Loro Piana and Cole Haan. (The Cole Haan versions are the ones Roman Roy wore.) Wolf & Shepherd even had the N.B.A. Hall of Famer Steve Nash playing basketball in its “dress sneakers.”
“Eventually, dress sneakers started appearing on ESPN sports commentators,” Guy said. Then Silicon Valley embraced them as a way to signal that the “move fast and break things” founders had reached a (slightly) more professional stage of business. From there, it was but a short jump to the wardrobes of the bankers who loved them — or at least their valuations — and wanted to demonstrate like-mindedness.
Which may be a reason that, as social media and its covert addictive strategies are literally, and increasingly, put on trial, the association may be losing its appeal — along with its symbolic shoe. While it offers the appearance of executive dress, the reality is a little less buttoned-up, and that discrepancy between pretense and reality suddenly seems telling.
My colleague Andrew Ross Sorkin, the editor of the DealBook newsletter at The New York Times and the author of “1929,” who is known to wear dress sneakers, thinks “the loafer is making a comeback” among the Wall Street set when it comes to what they wear with their suits — at least according to his anecdotal observations.
“This may be a belated post-pandemic rebound,” Sorkin said. It could also be a reaction to current fears about unemployment and the need to look as if you take your job seriously.
Or perhaps it is simply an acknowledgment that, as Guy said, the dress sneaker is sort of the footwear equivalent of “T-shirts with a tuxedo printed on them.” In other words: a kind of kitschy middle ground. In shoes, as in life, it may be time to commit.
Your Style Questions, Answered
Every week Vanessa will answer a reader’s fashion-related question, which you can send to her anytime via email or on X. Questions are edited and condensed.
