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Derek Guy: What Rishi Sunak and Keir Starmer are getting wrong about menswear

Rishi Sunak and Keir Starmer (Credit: PA Images / Alamy Stock Photo)

5 min read

Twitter sensation Derek Guy – aka ‘the menswear guy’ – looks at what Rishi Sunak and Keir Starmer are getting right with their style choices… and where the pair are going wrong

Whether they like it or not, how politicians dress sends a message to their constituents, shaping voters’ perception of them. 

When done effectively, their clothing choices present the best version of themselves, making them seem relatable and authentic while also inspiring confidence in them as leaders. When done poorly, their clothes distract from their political message. 

Even the scantiest garments can become sticky political points. The mere rumour that John Major tucked his shirts into his underwear – an idea floated by Alastair Campbell – ended up haunting the former prime minister throughout his political career and undermining his authority.  

So, in this election year, how do the two leading candidates stack up in terms of dress? And how can they improve? 

Rishi Sunak

If he weren’t the head of state of one of the most powerful nations in the world, it would be believable that Rishi Sunak secretly runs a menswear blog. He may be the most trend-conscious politician in British history. 

Strangely, his sense of dress is more fashion-conscious than the average man but also two decades out of date

The leader of the Conservative Party has been spotted wearing £95 sliders from the high-fashion streetwear label Palm Angels, £335 all-white minimalist trainers from the quiet luxury brand Common Projects, and £450 suede loafers from Italian fashion house Prada. So, the theories that his tailor, Henry Herbert in London, intentionally cuts his suits to be unusually trim – with cropped jackets, high buttoning points, razor-thin lapels, and often floodwater pants – in order to make him look taller are hard to swallow. 

Rishi Sunak
Rishi Sunak in March 2023 (Credit: Alexi / Alamy Stock Photo)

In most areas of dress, the Prime Minister dresses like a newly minted man who started shopping lavishly 20 years ago. It’s more likely that he has stuck with that silhouette because it’s the fashionable Thom Browne-led style he wore when he first started building a better wardrobe. Strangely, his sense of dress is more fashion-conscious than the average man but also two decades out of date, as the bleeding edge of fashion has long swung towards fuller silhouettes.

Sunak’s success in getting to No 10 proves that his expensive, high-fashion taste is not career-ending. But in a tough election year, one wonders why he doesn’t just opt for more traditional attire by visiting one of the many bespoke tailors on Savile Row, such as Henry Poole. Yes, the suits will be expensive, but with a conservative cut and a label hidden inside the in-breast pocket, no one would know. 

He should also see a shirtmaker on Jermyn Street, such as Budd, who will provide him with shirt collars with points long enough to reach his lapels (rather than the stingy collars he wears today). And pick up a tie from Drake’s, which will be available in widths that match the width of his new lapels (again, instead of the skinny lapels he wears now). Such outfits will be more timeless and flattering – and less likely to generate headlines.

Keir Starmer

Labour leader Keir Starmer’s tailoring is considerably better than that of most politicians, partly because his suits are cut in such classic proportions. His suit jackets bifurcate him about halfway from his collar to the floor; his lapels end halfway from his collar to his shoulder joint. His trousers are neither too slim nor too full, and his shirt collar points are long enough to reach his lapels, creating that smooth, uninterrupted line under his chin, leading the viewer’s eye up to his face. Most importantly, his jackets always hug his neck and never exhibit any pulling that would indicate an overly tight fit. 

Black dress shirts rarely communicate what the wearer wishes

Keir Starmer
Keir Starmer in September 2022. (Credit: Belinda Jiao / Alamy Stock Photo)

If it weren’t for the fact that Starmer needs to shorten the sleeves on some of his suit jackets – so they show that requisite half inch of shirt cuff and stop swamping his hand – one might think his suits are custom-tailored. For a man who has tried to present his party as a government-in-waiting, his suits telegraph a time-tested dependability. 

Where he stumbles is when he fastens the bottommost button on his suit jackets – a surprising faux pas for a man who has spent most of his life in tailored clothing. He also often wears dark worsted suits without a tie, presumably to seem more casual and relatable to voters. While that has increasingly become the norm in professional environments, Starmer would look much better in a navy blazer and wool trousers when going open collar. 

Finally, he should re-evaluate his penchant for navy dress shirts, which are so dark and inky that they can pass for black. Black dress shirts – a favourite among divorced men trying to rebrand themselves as young when hitting nightclubs – rarely communicate what the wearer wishes. 

These are the tiny details that someone like Starmer can’t afford to miscalculate in such a tight election year.

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