Derek Guy compared Ben Shapiro’s fashion sense to Ralph Lauren’s Polo Bear – and the shade was spectacular

Menswear expert and writer Derek Guy – @dieworkwear – has become the go-to account on Twitter/X for the bottom line on what is or isn’t a good idea in men’s fashions.

He isn’t only an essential follow because he knows what shoes to wear with that suit you like, but also because of his clothes-themed takedowns of people who are too big for their boots. Like when he compared Piers Morgan’s style to that of Kermit the Frog.

We’re not sure why anyone would invite Derek to pass comment on their style, unless they were confident that they were making smart choices. When right-wing commentator Ben Shapiro‘s team reached out, it soon became clear that his choice of clothes fell short of the standards adhered to by …Ralph Lauren’s Polo Bear.

The producer of Ben Shapiro's show reached out to me to see if I'd like to discuss Ben's attire on his show. Like with Piers Morgan, since Ben invited feedback, I will do a thread comparing him to a menswear icon—this time, Ralph Lauren's Polo Bear. pic.twitter.com/8BP0EBbWzL

— derek guy (@dieworkwear) May 16, 2024

This thread is superb – unless you’re Ben Shapiro.

1.

Unlike his colleagues, Ben's tailoring is not bad. Jackets have shape and fit him well. Compare his jacket to Peterson's, which looks like it was dunked in water (the small collar gap on Ben would be filled if he wore a dress shirt). Tonal seersucker in the second pic is cool pic.twitter.com/C7c1VK3xnn

— derek guy (@dieworkwear) May 16, 2024

2.

Unfortunately, a tailor can only do so much. They only make your clothes, not put them on you. For men of a certain social class, this task would have been historically performed by a valet. Such a relationship was hilariously depicted in the British TV show Jeeves and Wooster pic.twitter.com/8QB8GH4Oi6

— derek guy (@dieworkwear) May 16, 2024

3.

Most men today, including the ultra-rich, don't have valets, so they have to dress themselves. Ben is not very good at this because he doesn't understand the cultural language of clothing. He combines random things based on what catches his eye in the morning.

— derek guy (@dieworkwear) May 16, 2024

4.

For example, tan belts don't go with charcoal suits because tan leather was historically worn in the country and charcoal worsted was worn in the city. Likewise, a burgundy dress shirt with black jeans and tan sneakers says nothing except "I'm sad Express is closing." pic.twitter.com/TVmJjrHTpr

— derek guy (@dieworkwear) May 16, 2024

5.

Compare this to Polo Bear, whose outfits have a sense of culture and history. He knows how to marshal patterns, fabric, and color so that his outfits communicate something: a fishing vest with blue chambrays; a turtleneck with a pinstripe suit. Keep this in mind as we go forward pic.twitter.com/rImVU5ngez

— derek guy (@dieworkwear) May 16, 2024

6.

Ben here is wearing a tailored jacket with patch pockets (a casual detail). But the smooth, grey fabric is too close to what you'd expect to see on a suit, making the jacket too formal for jeans. It looks like he spilled something on his suit pants and had to change out of them. pic.twitter.com/Ln3qF6Dk3k

— derek guy (@dieworkwear) May 16, 2024

7.

Polo Bear knows that grey odd jackets need texture in order to convincingly pass as sport coats. The tweed herringbone here is perfect. Heavy textures and loud patterns make tailored jackets less formal, allowing you to bridge the gap in formality between your pieces. pic.twitter.com/ceppwLlLJR

— derek guy (@dieworkwear) May 16, 2024

8.

Here, Polo Bear is wearing a tailored jacket with jeans. Notice how he's reduced the gap in formality: a navy blazer and grey herringbone tweed are less formal than a suit jacket. He also wears them with textured knits, plaid shirts, and casual leather shoes. Success! pic.twitter.com/PWvxB5TzEe

— derek guy (@dieworkwear) May 16, 2024

9.

Here's another confusing outfit. The dressy navy jacket doesn't go with an untucked shirt, jeans, cowboy hat, and techy running sneakers. Ben seemingly thought the faint windowpane on his shirt and jacket would pull everything together. But he misses the bigger picture. pic.twitter.com/o5NFgTdV2c

— derek guy (@dieworkwear) May 16, 2024

10.

Polo Bear knows that if you want to create a Westernwear outfit, you need to wear things like barn coats, fringed leather jackets, chambray shirts, henleys, leather vests (if you're daring), and cowboy boots. The red bandana around the neck here is jaunty. pic.twitter.com/m5ExUsjWXF

— derek guy (@dieworkwear) May 16, 2024

11.

Successful outfits don't have to slavishly follow history. But see how Ben wears a cowboy hat with a blue dress shirt, jeans, and a black dress belt (confusing). Polo Bear creates a coherently rugged look: sportswear jacket, chunky knit, and hiking boots. Hat now looks at home pic.twitter.com/6ebVNTiEYL

— derek guy (@dieworkwear) May 16, 2024