Navy suit trousers don’t usually cause a stir, at least not in politics where they abound. Unless, that is, they hover two inches above the shoe, as Rishi Sunak’s did on a visit to a gas plant in Aberdeenshire on Monday. The prime minister might be wearing shorts in Disneyland right now, but images of his shrunken trousers flooded social media long before he boarded the plane, accompanied by armchair theories that it was surely a trick to make the 5ft 6ins PM appear taller.

Menswear critic Derek Guy disagreed. “Lots of conspiracy theories on why Sunak wears such short trousers … but my theory is simple … Sunak is a vaguely trend-aware guy, but just a little behind the times,” he wrote on Twitter, his preferred medium. “I don’t think he has a grand theory for how short sleeves and pants make him look taller”.

Derek Guy is a menswear writer, critic and prolific Tweeter based in the San Francisco Bay Area. Evasive about his age, he hides behind his Twitter avatar – a drawing of Nixon’s debonair attorney general Elliott Richardson – and describes himself “a guy who lives alone with a cat”. Guy, who writes on his blog Die Workwear, began writing about fashion in the mid-00s, first on blogs and then, in 2011, via Twitter. Back then, it was the medium through which Beyoncé announced her pregnancy and Osama bin Laden’s death was first leaked. “I was just making in-jokes to guys who were interested in clothing”.

Today, Guy has almost half a million followers, though notoriety came at a price, largely the algorithmically curated “For You” tab which landed him in the feeds of people who didn’t follow him. After calling out the marking up of a US watch company, he saw his following balloon. “It was very stressful [at the start]. I thought I was getting cancelled,” he says. “Now I just can’t keep up with the replies.”

Guy says he is as shocked as anyone by his sudden ubiquity, and that he still doesn’t know why his tweets have got so much traction. He also says he is a fashion nerd who only writes about menswear because he doesn’t have the required “language” to talk about womenswear.

baffling to me how the wealthiest UK prime minister in history could live just steps away from savile row, the single greatest concentration of skilled bespoke tailors, and end up paying $2k for a MTM suit with sleeves and trousers 2-4" too short pic.twitter.com/0IYg87ZB1O— derek guy () July 31, 2023

Still, in most other circles he has become as beloved for his granular takes on cashmere as his critique of male politicians on the 2024 campaign trail. His tweets are somehow censorious without being mean, with Guy insisting he only punches up. “I would never do it to some guy on the street,” he says. “[Critiquing fashion] is different to critiquing other forms of culture. I could tell you you have bad taste in music, but if I say your clothes are ugly I am telling you you are ugly,” he says. And while he’ll happily unpack Jordan Peterson’s strange fabric choices ranges, he thinks it’s “distasteful to comment on people’s dress – even though yes, I do it all the time”, he says. “I just don’t find cruelty to be fun,” he says.

Guy tends to target politicians in the US who “dress poorly”, and doesn’t know enough about UK politics to fully comment. But as anyone in politics attuned to the nuance of presentation while fending off accusations of spin knows there is usually one sartorial solution: the centrist blue suit. From Sadiq Khan to Keir Starmer, it is versatile, uncontroversial and ubiquitous. Guy says he is familiar with this look. “My politics means that I target people on the right,” he says. “But I think all politicians dress equally badly”.

He’s only really aware of Jacob Rees-Mogg, Boris Johnson and Sunak. But he knows that the PM gets his suits tailored at Henry Herbert, a tailoring company in London’s Holborn area known for its younger clientele. He suspects they are working off a block pattern. “They’re either made to measure or they’re drafting a bespoke pattern, made to be a 2000s silhouette”.

“It’s very weird that his suits fit like this when he lives in London, has access to tailors, and [has money],” he says. “I suspect [the suit] was meant to look trendy. But if he just went to a more traditional Savile Row tailor he’d probably get something that [fit better]”. The Guardian contacted the tailor but has yet to receive a response although, earlier this week, its owner, Alexander Dickinson, told Yahoo that this style is generally worn by “young [guys] in the city”. Sunak is 43.

It’s really only a trendy look for men in their 40s, not their 20s he says – or rather “guys in their 40s who were wearing trendy clothes 20 years ago, which he maybe was?”. So, less a lapse in style and more a bid to make himself look less stuffy? “Yes. He chose a hip tailor because that’s him – a man who is vaguely aware of trends,” Guy says. This also explains why he wears Palm Angel sliders, £190 Timberland boots and £450 Prada loafers, pieces typical of a wealthy middle-aged man. Guy also credits – or blames – Sunak’s “fashion-conscious” wife. “She probably just doesn’t want him in a fussy suit,” he says.

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Guy became interested in clothing in the late 90s after growing up around “guys who were part of the Lo-Life”. This subculture was defined by its members who wore Ralph Lauren Polo shirts and came at a time when hip-hop was starting to intersect with fashion. “I admired the dress and became more interested in Ralph Lauren, and that’s when you start to learn about its tweeds and button downs, and then tailoring,” he says.

He admits to spending a lot of time on Twitter. Sometimes people will send him photos, which is why he was tweeting images of Spain’s King Felipe at 2am after Wimbledon, although he often repurposes his previous writing and uses his own picture archive.

As for Sunak’s suit, he blames the market rather than the man. “You have to be an enthusiast to get a good suit, and the majority of people aren’t – you can’t just walk into Tom Ford.” He pauses. “It’s also hard to find people [you trust] who will tell you if something fits.”

This article was amended on 5 August 2023. An earlier version misspelled the name of King Felipe of Spain as “Philippe”.