Good morning. Andrew here. For the last decade or so, men have been pairing sneakers with suits and blazers at the office — myself included. But a shift is underway: Loafers and traditional dress shoes are officially making a comeback. DealBook contributor Calum Marsh takes us inside the evolving landscape of work-from-office fashion. Also: Sarah Kessler has a fascinating Q&A with the head of a start-up that is building an A.I. model designed to operate as an autonomous C.E.O. And don’t forget to test your news IQ with this week’s quiz. (Was this newsletter forwarded to you? Sign up here.)
The return of dress shoes
Ben Kriz, a men’s fashion writer, remembers the point at which the sneakers he wore to the office no longer seemed cool. “All the older guys at the office started wearing sneakers with their suit trousers and sport jackets,” said Kriz, who was then in his 20s. So he opted to distinguish himself — by donning a pair of buffed and burnished loafers. Kriz is, by profession, geared toward staying ahead of the trends. But young people in workplaces everywhere are catching up to him. After years of flagrantly casual office attire that followed workers back to the office after the pandemic, young people are now increasingly going in the opposite direction: turning up for work in dress shoes. Earlier this year, Esquire described the trend as the loafer’s “big generational shift,” describing how younger consumers “were bypassing sneakers in growing numbers.” And in January, The Times UK deemed 2026 “the year of the loafer.” Derbies and oxfords have also unexpectedly become hip. At the same time, wearing sneakers to work — whether the upscale brands like A.P.C., Common Projects, Zegna and Maison Margiela or the classic Adidas and Nike — has become a sign of something else entirely. “It’s the classic generational reaction: If your boss comes in wearing sneakers, the natural reaction is to do something different,” Kriz said. “It’s like what happened with jeans.”
While the office sneaker might still seem to some a way to modishly break stodgy business attire rules, younger workers have been clear on the point: Kicks at work now scan as uncool. Big sneaker brands are feeling the pain. In a January report, Bank of America concluded that the sneaker industry was entering a period of slowing growth and possibly decline, even downgrading Adidas, maker of Stan Smiths, by two notches to a “sell” rating. The surging interest in formal footwear fashions has simultaneously been a boon for both high-end luxury retailers and heritage brands with classic shoe offerings, like Allen Edmonds, the Wisconsin-based retailer. Nick Wooster, the brand’s consulting creative director, said that they have “absolutely” seen a recent increase in interest in their handmade leather loafers and derbies among younger customers. “Sneakers dominated for a long time, and they are not going anywhere,” he said. “But a great loafer or derby works in a meeting, it works at dinner, it works on a plane. Classic shoes tend to do that better than anything else.” Even sneaker brands are trying to be more dressy. Brendan Dunne, the senior director of customer community and engagement at the footwear resale site StockX, said that while “we’re definitely seeing a shift” that has brought formal styles back to the office, it’s “a little more nuanced than just consumers giving up sneakers to go after loafers.” In fact, he said, “sneaker brands themselves are absorbing formal aesthetics,” releasing more formal versions of their own hallmark shoes. Puma unveiled a variation on a classic Mary Jane in 2025; both Adidas and Nike have released low-profile ballet flats; and a number of the top sports brands have gone all-in on patent leather shoes that skirt the line between sneaker and something more formal. “I think the appetite for something different, and in many cases dressier, is real,” Dume said, but some consumers are “still reaching for it through sneaker brands.” He pointed to the New Balance 1906L, its “sneaker loafer,” as a case in point: StockX has seen more than 15,000 sales of the model since it was introduced last year. (Though some critics will claim that the so-called “snoafer” was a flop.) “What we’re seeing right now is something we’ve seen before,” said Matt Halfhill, the founder and chief executive of Nice Kicks, a media company that focuses on sneaker culture, said that, since about 2023, in offices all over America, “we’ve had this quiet luxury, leather loafer, growing up thing,” but he predicted that, as in the past, younger consumers would eventually return to sneakers again.
Yang-Yi Goh, the senior style editor at the men's wear magazine GQ, told DealBook that after the pandemic, “people just wanted to feel a little more dressed and put together,” particularly at the office. “I think over the last half decade or so we’ve seen more and more young men investing in loafers, derbies and the like,” Goh said. So much so that in one story for GQ he recently edited, a writer said he was looking to give up his loafers. He’d noticed all the guys he was with were wearing matching shoes.
Employers cut 23,000 jobs last month. An unexpectedly downbeat jobs report — which also revised down gains reported in previous months — may buy the Federal Reserve more time as it considers whether to raise borrowing costs to combat persistently high inflation. But while the new numbers suggest a weaker economy than many perceived, which strengthens the position that rate increases aren’t immediately necessary, forthcoming inflation data will play an outsize role in the central bank’s decision making. The Trump administration laid out a plan to scrutinize A.I. models. Its framework would review only “closed” models, like those from Anthropic and OpenAI, which do not publish their underlying code. It does not plan to review “open source” models, which have computer code available to the public to download and modify. That could be a boon to companies like Meta that have used open source to create products that compete with the leading A.I. companies. Google announced a major shake-up. Demis Hassabis, the chief executive of the Google DeepMind lab, will become chair of the unit and chief scientist of Google’s parent company, Alphabet. Koray Kavukcuoglu will take over the daily operations of Google DeepMind. And Jeff Dean, Google’s previous chief scientist, is starting a new A.I. company. Other big deals: Iran said it’s nearing a deal with Oman to restore safe passage through the Strait of Hormuz. FIFA’s president apologized for a plan to attract private investors. And the software company Airtable, which had a peak valuation of $11 billion, said it would sell itself for about $1.29 billion. How to build an A.I. C.E.O.Artificial intelligence wasn’t quite cool yet in 2017 when Sam Pasupalak sold his A.I. start-up Maluuba to Microsoft for $160 million. Now, A.I. is on every C.E.O.s lips, and Pasupalak is not impressed. “Everyone’s so excited with the A.I. software engineer,” he said, “But it’s so easy.” For his new start-up, Pasupalak and his co-founders, Sumit Pasupalak and Kaheer Suleman, have set their sights instead on something that is less defined and logical than programming: running the whole business. Their company, Skyfall AI, aims to automate the role of C.E.O. And it’s currently shopping for a handful of software as a service (SaaS) companies — which offer software tools to customers via the cloud — to test their technology. Pasupalak spoke with Sarah Kessler about the idea. What makes automating a C.E.O. difficult? Large language models, LLMs, will never be able to plan on a longer horizon because they’re based on next word direction. A C.E.O. does a lot of high stakes decision making under uncertainty. And has a lot of sample efficiency. Sample efficiency? The human brain operates at like 20 watts an hour. So it’s 480 watt hours in 24 hours. For an LLM, a big reasoning decision might require a thousand watt hours. I think that’s extremely inefficient and expensive. So in order to circumvent these problems, we have two research focuses. One is world modeling, and one is continued learning. Your first environment for testing A.I. at business building was the game Roller Coaster Tycoon. Now you want to buy businesses to use as experiments. How is that going? We are at the final stages of closing the first SaaS acquisition. We intend to buy a bunch of companies by the end of August. We’re going to platforms — like acquire.com, TrustMRR and others — where you can buy micro SaaS businesses. And they have like up to a few hundred thousand in monthly recurring revenue, because we don’t want to spend more than a million dollars in the experiments right now. Next year, if these experiments succeed, we’re going to go to 10 million to a 100 million dollar businesses. What will the process actually look like once you buy this company? We want to move from the co-pilot experience to a fully autonomous experience, like how I interact with my managers or my researchers or my employees: They are able to carry out the entire tasks end to end without me being involved. With the businesses we are acquiring right now, we don’t want the employees to be there, or to have minimal involvement. So basically we should be setting the revenue goal, and the company should figure out, how do I run the go-to-market channels? What should be the exact customer acquisition channels that should be running? Do I need to do product enhancements if the sales are not going as fast as possible? It has to make all the decisions that a C.E.O. would make for your specific start-up. And so a lot of unsolved research problems, obviously, but that’s the challenge. What is left for humans to do? Human relationships within work can never be operationalized. I don’t think A.I. can motivate employees. But will there be employees to motivate in the vision of this autonomous company? These first businesses we’re trying to automate will have, let’s say, only one to three employees or something like that. But this will democratize the technology so that everyone can be an entrepreneur. If you have an A.I. C.E.O. that can do all your operational tasks, then almost everyone in the world can be an entrepreneur. That unlocks economic value and for the entire world at a much bigger scale than it is right now. When an assistant won’t cut itThis question comes from a recent Times article. Click an answer to see if you’re right. (The link will be free.) Executive assistants are old news. Now a growing number of executives want a “chief of staff,” with job postings for the role increasing 85 percent since 2020, according to Indeed. The difference? An executive assistant “figures out what time something goes on the calendar, but a chief of staff figures out whether it should go on the calendar at all,” said Clara Ma, founder and C.E.O. of Ask a Chief of Staff, a networking platform that brings together chiefs of staff across various industries. According to a survey she conducted, how much does the position typically pay? We hope you’ve enjoyed this newsletter, which is made possible through subscriber support. Subscribe to The New York Times. Thanks for reading! We’ll see you Monday. We’d like your feedback. Please email thoughts and suggestions to dealbook@nytimes.com. Follow DealBook on Instagram: @nytdealbook
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