The Menswear Guy judges the wardrobes of three ‘normal’ men challenging a fashionable mayor

Derek Guy, known for offering men’s fashion advice and the occasional hot take as the Menswear Guy, just so happens to be a San Francisco resident. He’s not especially invested in November’s mayoral race — “I’m very detached from San Francisco politics,” he said — making him an electorally neutral fashion arbiter. 

So we asked the style expert to offer insights into how the leading male mayoral candidates dress and where they might make improvements while they’re out there glad-handing the public and kissing babies.

Regarding Mayor London Breed, who is given to monochromatic powersuits in bold hues and frequent changes of hairstyle, all Guy would say is that she “falls into the ‘She looks nice’ category.” He’s a menswear expert, he insists, so asking for his thoughts on women’s fashion would be like asking an English professor to hold forth on German lit. 

Fair enough. But the Menswear Guy wasn’t as modest when commenting on Breed’s most serious challengers — philanthropist and Levi Strauss heir Daniel Lurie, former interim Mayor Mark Farrell, and Supervisor Aaron Peskin — who present very different sartorial stories. 

Here, in Guy’s words, is what the candidates’ fashion choices say about them.

Jeans are a part of his brand, and he’s wearing a white shirt to kind of cling to the idea of business professionalism. I think it would be better if he wore a blue Oxford button-down, or even a chambray work shirt — which his company [Levi’s] also sells. 

There are photos of him wearing suits with the last button buttoned, which he should not do. He doesn’t wear tailored clothing. He’s a very thin man, and if I were advising him, I would say put on jeans and a light-blue Oxford shirt and wear a tweed jacket. Or, in the summer, you can do a cotton sport coat, and that would give you the professionalism you want to project.

If he does wear a tailored jacket, I wouldn’t wear the jeans. I don’t know what model he wears, but probably 501s. I would say go to the Levi’s Vintage Store that does historically accurate versions of things they did in the past and get 1947 501s. The ones he walks around in are too low-rise for a tailored jacket.

Note: The Standard texted Lurie about his preferred style of Levi’s. “511s!” he replied.

He’s often wearing a charcoal or navy suit with a tie, and I think he should stick to that. It’s not the best, but it’s not a terrible cut. There are photos of him with a suit with no tie — I think if you’re wearing a dark, worsted suit, you should wear a tie. Without one, it’s like the night sky with no stars.

In some instances, he’s wearing what I would kindly describe as “middle-class sneakers.” Thirty years ago, if you were running for office, you would never wear sneakers, but there’s a new category that’s still sneakers but telegraphs that you’re middle-class, not like Jordans or Air Force 1s. The new sneakers are ugly. I think he should throw on dress shoes. 

He dresses not, like, schlubby, but like a normal dude. San Francisco is a very dressed-down town, so naturally he will dress down, but if you just campaign in jeans or tailored trousers and a dress shirt with a jacket, you would look better if you wear dress shoes instead of sneakers. Aesthetically, it’s not very pleasing. 

The most notable thing is he wears a terrible tie knot, a really fat tie knot. He doesn’t cinch them very well, so you end up getting almost no discernible shape, and it looks kind of ugly. But most ties are ugly. 

The other thing is he often has really bad taste in shirts. He wears this really bad shade of blue or lavender. If you don’t have a very good eye, you’ll never go wrong with white or light blue. That will never look bad with a tailored jacket. If you’re not really into clothing, just don’t experiment with color, ’cause you don’t have the eye. 

If you’re wearing tailored trousers, get them in gray or tan. If you’re wearing jeans, just get blue; if you’re wearing chinos, get tan. And if you’re not into clothing, be very careful about where you buy ties. Just go to Brooks Brothers or Ben Silver and choose a very conservative tie. They will be very safe.