Say What You Will About Trump Adviser Roger Stone’s Politics. But His Style Knowledge? Unrivaled.

Alexandra Mondalek
Roger Stone, a longtime political provocateur and adviser to President Trump, leaves a courtroom in New York on March 30. (Photo: Seth Wenig/AP)

“My guy looks like a Czarist Mr. Peanut,” is how one Twitter user described Roger Stone after glimpsing a photo of the longtime Trump adviser on Inauguration Day. Other choice descriptions in the merciless, 80-plus tweetstorm, retweeted by thousands and covered in the fashion press: “Babadook,” “the villain in the kids’ movie that stars a talking car,” “a Count Olaf disguise.”

In the photo, Stone is standing with his wife and wearing a three-piece morning dress ensemble, replete with a top hat and pair of circular, black-framed sunglasses that are requisite to his persona.

It was not the first time his style has been bait for Internet trolls. In one appearance on the Alex Jones Show (where he is a frequent guest), the 64-year-old wears the same black glasses as he did on Inauguration Day, but with a Kangol wool hat and a leather jacket. Again, the trial-by-Twitter was harsh, dubbing him a “racist Spike Lee” and “mummified Bono.”


But Stone, who meets with Yahoo Style at a New York City Starbucks in a bold getup consisting of an Anderson & Sheppard three-piece custom suit and navy knit tie, is not one to be easily thrown off his fashion course.

“Everybody has their own style,” Stone says. “When young men want to talk to me about clothes, which is fairly often, I say to them, ‘You don’t want to look like me, you want to look like you. You’ve got to develop your own style.'”

He’s developed his, appropriately enough, with a careful eye on political history. “I’m wearing brown suede shoes and a gray suit,” he notes, sipping his sixth espresso quad shot of the day (“totally, totally addicted”). “That was completely unacceptable until 1938, when Edward, Prince of Wales, came to New York, and he was wearing the gray suit and calf shoes — reverse calf, or suede, as we know them today — and suddenly that was the style.” 

Stone worked as a campaign manager for Kristin Davis, who once supplied escorts to then-New York governor Eliot Spitzer. (Photo: AP Images)

Also part of his look during the Yahoo Style interview: a pair of circular-framed prescription glasses, these from E.B. Meyrowitz and Dell Opticians in midtown Manhattan (“They have been around so long, they made glasses for Theodore Roosevelt,” Stone notes); and a 30-year-old Louis Vuitton tote, stocked with a New York Post and the New York Times and fitted with custom straps that can fit over his shoulders, broadened from years of bodybuilding. By Stone’s side is Kristin Davis, a woman once known as the “Manhattan Madam,” imprisoned in 2015 for providing escorts to clients including former New York Gov. Eliot Spitzer. She was providing “moral support” to Stone earlier in the day, as he appeared for jury selection in a defamation case against him.


While many eagle-eyed Twitter users may be newly acquainted with Stone because of his fashion sense, he’s been a presence in politics for more than 40 years. There was the Nixon administration, wherein he was the youngest person to be called to speak before the Watergate jury (now it’s his back tattoo of former President Richard Nixon’s face that may be more well-known.) He co-founded the National Conservative Political Action Committee in 1975, which helped propel Ronald Reagan to the presidency. And today he works as a political consultant, best known as “the dirty trickster” who sabotages the governing dreams of Republican opponents by any means necessary.

Oh, and he’s being investigated by the FBI for possible connections between Russia’s interference in the U.S. election and the Trump campaign. He says he has nothing to hide, and welcomes an invitation to testify to Congress — in public, under oath, with no immunity.

Stone has been an on-and-off adviser to President Trump for more than three decades, way before the current leader entered the political stage. Of Stone, Trump told the New Yorker in 2008: “Roger is a stone-cold loser. He always tries taking credit for things he never did.” More recently, though, the Trump-Stone thermostat has warmed. “Roger Stone was just banned by CNN their loss! Tough, loyal guy,” Trump tweeted in February 2016.


Over the last few months, Stone has embarked upon a media blitz promoting not only a new book, The Making of the President 2016: How Donald Trump Orchestrated a Revolution, but also a new Netflix documentary of which he is the subject, set to premier at the Tribeca Film Festival in late April. And to be sure, he’s defending not only his political record, but his sartorial record too. 

It’s something he’s been at for a while on social media, as, much like Trump, Stone is prolific, if not totally unfiltered, on Twitter. He was quick to defend the Alex Jones Show outfit, tweeting, “Some people are so lacking in style that they don’t get the homage to Bobby Seale and Panther Style.”


So say what you will of his ultraconservative politics, but Stone’s style record is inimitable insofar as it abides by classic rules of dressing: Don’t wear light colors if you’re heavyset. Don’t send your suit to the dry cleaners too often or it will bubble. A double-breasted navy blue blazer is a staple. A proper fit is paramount.

And while most of his Internet hot takes tend to indulge his far-right conservative followers (“The more upset Hillary supporters are about losing the more I enjoy it. Now we must send Hillary Clinton to prison for her crimes,” for example), he quips on fashion just as well. In 2015, he wondered whether Yeezy, Kanye West’s clothing line, is a joke, calling it a “fashion wreck.” More recently, he took a page out of the POTUS tweet playbook when he called Meryl Streep’s Givenchy dress at the Golden Globes “a disaster” and “sad.”

Roger Stone talks to reporters on March 30, wearing the circular, black-framed glasses for which he’s known. (Photo: Seth Wenig/AP)

He is also men’s fashion editor for Tucker Carlson’s conservative site the Daily Caller and has his own style blog, Stone on Style, on which he features an annual best- and worst-dressed lists. Last year’s bests were Fox News host Kimberly Guilfoyle and disgraced former Breitbart editor Milo Yiannopoulos. The worst? Hillary Clinton and Rand Paul.

He shares plenty of highly detailed fashion musings with Yahoo Style, on everyone from the Kennedy brothers to Thom Browne. “I think [JFK’s] style, which is your absolute unalloyed, preppy, Ivy League —  which is also true of Bobby and Teddy as well, they were all great dressers — is not premeditated,” he says on the former. “It’s interesting that John Kennedy pioneers the two-button suit. Until then, most men’s suits were three-button, with that top button pretty high. The two-button suit [that] we consider the epitome of American style was made in London by a British tailor, to Kennedy’s specifications. He described the suit, and they made it. Once he was seen in it, that was it. The three-button suit was gone, the two-button suit was standard.”

Stone likes Browne, but notes it’s not a look that would work on him because of his “heavy thighs and heavy calves” from years of running. “That’s what started me on custom clothing. I didn’t have any choice,” he says. “I had 44-inch shoulders but a 30-inch waist. So buying… a suit off the rack meant the jacket would fit, but when you altered the pants, the pockets in the back would be right next to each other and that doesn’t work. I had to get things made to have them fit right. Once you do it, you become addicted.”

Now he lets Alan Flusser make him custom suits that duplicate something he says he saw on ’30s jazz singer Cab Calloway. The New York City–based Flusser, he says “has a taste level, in terms of fabric and fit, that you can’t find anywhere else in the United States.” He can’t say the same for “Wall Street types,” who are, Stone believes, “confusing expensive with good — expensive with stylish. They’re not necessarily the same thing.” These men might wear “Zegna suits, Britton suits,” he notes, but “I think a lot of these guys operate on the price tag, rather than whether the fit is right for their body type.”

Roger Stone addresses the conservative group America First in March. He spent much of 2016 campaigning for Trump. (Photo: Michael Ares/Palm Beach Post via AP)

Speaking of suits, when asked who within the Trump orbit he’d most like to give a style makeover, Stone quickly names press secretary Sean Spicer, whose outfits have elicited jokes from the public and criticism from the president. “He’s got very, you know, classic Ivy League, prepster-inspired clothing, but he needs higher quality. His lapels are too small, his suits don’t fit, and his choice of neckwear is spotty,” Stone says. “He has to be given credit, though. He’s trying and clearly improving.”

Of Trump himself, Stone confirms much of what’s already been said about the president’s style — that he’s a “Brioni man” who invented the solid red power tie in the ’80s. When asked whether the man who branded himself a nationalist champion on the campaign trail should favor U.S. clothiers, Stone says, “It would probably be good if he bought American,” adding that a small, Tennessee-based menswear manufacturer, Hardwick, did make a recent gesture. “I just saw like two days ago, they’re sending the president a suit,” he says. “Legally he’s allowed to accept if he donates it to the Smithsonian when he leaves office. I think that’s a step in the right direction.”

And while Stone is not officially tied to the Trump administration in its current iteration, he’s never too far from Washington drama. In fact, he’s about to be at the center of it — a fact not lost on this image-conscious operative.

“I’m already planning what I’ll wear for Congress,” he says. “For the hearings.”

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Alexandra Mondalek is a writer for Yahoo Style + Beauty. Follow her on Twitter @amondalek