Mr. Stone’s 11th Annual Best & Worst Dressed List For 2016

Posted on January 1, 2017 by Roger Stone

In our 11th year of Mr. Stones International Best and Worst Dressed, we thank Mr. Blackwell for inspiring this annual tradition, which I carried on under his name for nearly a decade.

I am honored to have assumed this responsibility and continue to cover Mens Fashion for The Daily Caller. As the state of fashion in America has declined rapidly, we have seen some really horrid faux pas, but 2016 has also brought some alternative styles that make sense for the growing Millennial population.

An important point we make each year is that what passes for style today is in fact fashion. After monitoring the worlds of media, sports, politics, music, and fashion we have narrowed down who has style and who truly does not.

Fashion is ever-changing, while style is timeless.
Some on this list will excel in both categories, while others offer a well-rounded understanding of both.

This years list is full of new faces and we are also debuting our Lifetime Achievement Award, which honors those who have demonstrated an everlasting dedication to style.


Kimberley Guilfoyle
The Fox News firecracker is another person rumored to be in consideration for a position with President-Elect Trump and we think shed make a strong addition to the team. Guilfoyle is primarily wears a wide array of colors during her segments hosting The Five, but the collection of black dresses we saw her wear at several events in 2016 that caught our eye. She has earned a spot for the first time on our Best Dressed, see you next year Mrs. Guilfoyle.

Milo Yiannopoulos: The alt-right provocateur and the face of Breitbart is known for his brash commentary against feminism, political correctness, Radical Islam, and other societal drags. A gay conservative, Yianopoulos is a clotheshorse who regularly visits Londons Saville Row for his formal-wear. On his Dangerous Faggot tour across Americas college campuses, he sometimes blends a traditional British style with more ostentatious elements. This is his first year on the list and we cant wait to see what he wears at the Deploraball ahead of DJTs inauguration.

Jim Brown:
Pro-Football Hall of Famer and actor Jim Brown isnt as spry as he was during his days as an NFL Fullback, but he certainly has not lost his drive to look good. His emergence from Trump Tower, weeks before the inauguration of President-elect Trump with linebacker Ray Lewis, was the first time many Americans had seen the legend on the national stage in years. He has always donned an all black suit, shirt, and sometimes tie combo with much enjoyment. However, at the tower and in the following media blitz, his ensemble was on point. His style inspired football greats like Shannon Sharpe not only on the field, but in their wardrobe.

Owen Shroyer: Dogged truth seeker/reporter on the rise. Shroyer is one of the rising talents at Alex Jones InfoWars alternative news network. Bombastic during his man on the street style reports, Shroyer is amazingly put together no matter the climate or setting. The cut/fit of his suits and shirts are form fitting, but not busting at the seams (Daniel Craigs Bond wardrobe). Our true admiration though is for his favoritism of a spread collar to accompany the thick knots of his ties.

Anton Yelchin: A tragic loss of an amazing acting talent. that was way too young to leave us. The raspy voiced Russkie was a simple dresser and often would arrive to red-carpet events with everything but a tie. While we dont normally like this in formal settings where suit and ties are customary, the way he carried himself in these instances let us know he was not doing so in a trashy fashion. Another item we enjoyed in Yelchins wardrobe were his thin cotton blend blazers that were somewhere in between a cardigan and evening jacket. Our heart breaks for his family and friends for those wanting to see one of his final works we recommend watching The Green Room, a superb effort by Jeremy Saulnier.

Jenny Lewis: Indie rocker Jenny Lewis might be a new favorite of mine, thanks to Alt Nation and XMU on Sirius, channels 34 and 35 respectively. She has been around the block with iconic bands like The Postal Service and several under Conor Oberts tutelage at Saddle Creek Records. As I became more interested in her cleverly crafted stories, we felt it necessary to review her fashion+style choices as well. The folksy wunderkind is part June Carter and part Emmylou Harris. Her promotional style is more hippie psychedelic, which we understand, but dont like for regular use. Where she really shines is with her onstage display, this is where she evokes old folk songs with sumptuous fabrics that lean to the dark end of the color spectrum. Rich burgundys, somber blacks. This is her first year on the list, following in fellow indie rocker Lykke Lis footsteps.

Michael Smerconish: Despite our heated differences during the 2016 election, Smerconish always looked good when we were battling on the airwaves. Don Lemon should look to him if he wants to get back in our good graces. Congrats, now lets Make America Great Again!

Jon Yapo: Foley & Lardner Public Affairs Advisor Jon Yapo leads a group of well dressed Dandies in the all important I-4 corridor of Central Florida, flanked by GrayRobinsons Chris Carmody and Southern Strategy Groups Alex Setzer. His haberdasher is by appointment only and only works on recommendation from an existing client. What we admire about Yapos vibe is his attention to detail. Every part of his ensemble is made not only for style, but to accentuate something about his personality or lifestyle, from the interior of his jackets to the pocket squares. Yapo could end up in the Hall of Fame if he plays his cards right and sets us up with his guy. Mr. Yapo joins the list for the first time and is expected to be a repeat in 2017.

Zendaya: Her style is so iconic, Barbie made a doll based on her look, and the actress, singer and dancer can switch from feminine to masculine looks without dropping the style ball. Still, maybe don’t wear a mullet again, OK?

Tomi Lahren: Ms. Lahren of Glenn Becks The Blaze burst onto the scene during the 2016 election style with her poignant video essays and killer looks. She is the primo blonde bombshell you always failed to land after meeting her in the College Republicans. Mastering a style that accommodates a rotating wheel of colors and cuts, Lahrens outfits ranged from revealing to quintessential WASP Ivy League. This is her first time on the Best Dressed list and likely wont be her last.

Carly Fiorina: Listening to Carly Fiorina shriek about Geo-political issues makes anyones head want to explode. However, she was the undisputed style and fashion boss in the stable of GOP contenders for President in 2016. Business chiq defined her, as she wanted to appear serious, while regularly selecting a bold color or texture with her wardrobe. Women looking to master walking in high heels, review this video of Fiorina walking onto the debate stage to Kelis Bossy.

Blake Lively: In 2016, this 29-year-old mother of two and wife of Deadpool actor Ryan Reynolds proved to be a master of street style, pregnancy style and Hollywood glamour. Some fashion writers even suggested First Lady Michelle Obama was stealing fashion looks from Lively when Michelle appeared with the president at a Christmas event with Marines in Hawaii this year. Actress Blake Livelys sexy maternity style made a mark on 2016 fashion.

Ben Gibbard: We have wanted to place Death Cab for Cutie front-man Ben Gibbard on our Best Dressed list for several years now. Fortunately, he seems to have given his hipster indie shtick some consistency in 2016. While Gibbards Million Dollar Loan was meant to galvanize Millennial votes for Hillary Clinton, we have to recognize his immense influence among 18 to 35 year old Indie Millennials who actually voted Trump. The women want to marry him and the men dress like him. Gibbard favors the slim fit button up shirt, with the sleeves rolled up midway. The top button is buttoned or left open with an accompanying sweater. Neutral grays, blues, charcoals, and blacks are staples for Gibbard. We dont see formal wear often from him, but thats okay he gave us Transatlanticism after all. Well be firing up their single The New Year to march into 2017!

Justin Trudeau: Canada’s 44-year-old prime minister has some of the best tailored suits among world leaders, which are no doubt helped by his fit physique. Seriously, the man is known for doing push-up challenges.

Elle Fanning: Anything the younger sister of Dakota Fanning hits the streets with is on point. She looks particularly magnificent in cream and royal/navy blue colors. I first saw her when browsing Amazon Prime and finding this years Neon Demon and started my research afterwards. Unlike other young female stars, she is not looking to emulate the grotesque styles of Miley Cyrus or god forbid Lena Dunham, who has landed on the Worst Dressed list again this year. Elle Fanning could compete with Pippa Middelton, no doubt.

Winona Ryder: The all but forgotten mega-star of the late 90s and early 2000s captivated us in a way we have not seen her with this years Netflix original series Stranger Things. Ryders latest public appearances have showcased her Johnny Cashesque ability to make anything in black look like a million bucks on her petite frame. We have occasionally seen deep blackish blues, which look even better on her. This is her first year on the list and we cant wait to see what season two of Stranger Things has in store.


Hillary Clinton: Were not sure if the two-time failed presidential candidate has ever worn anything resembling acceptable style or fashion. 2016 brought us the Dr. Evil version of Hillary Clinton and many other smock style outfits that reminded us of third world despots and upstart super-villains. At times, many even reasoned her oversized and bulky collection was housing some type of medical device to keep the campaign going. There is absolutely no hope in her becoming Commander in Chief or a style icon.

Rand Paul: The son of libertarian icon Ron Paul has shown absolutely no interest in rehabbing his odd and poorly sized suits. Were not asking him to trade his JC Penny multi-blend suit for a $10,000 properly tailored Brioni. Were just asking he get a shirt with the proper sized color and a decent tie knot.

Cenk Uygur: The increasingly corpulent co-founder of The Young Turks is always shilling for the revolution, but he cant even dress for the revolution. All black protest gear with a bandana over the face would let him access his inner commie. His obsession with drab sport coats, often times with a Hanes multi-pack type cotton shirt underneath does not inspire. It makes him look more like a third rate community college professor.

David Brock: The top Clinton aide who ran a relentless smear campaign against me under his Media Matters banner was once a sharp dresser. He was also once a conservative, which means he has not only committed crimes against freedom but also against fashion. Its hard to understand how he cant put together a proper outfit, considering the fact that he has made tens of millions in Clinton Cash under questionable circumstances. Brock consistently has problems matching the proper knot with the right collar and his hair is either deflated or molded into an electrified patch of silver.

Ana Navarro: We wish for her a brain. Past that, its possible that she is on the same level as Hillary Clinton with her fashion and style choices. Her odd affinity for scarves and other neck garments is the most egregious offense of many. The only thing worse than listening to her talk is enduring the horrors that will befall your eyes when you look at her. No self-awareness about her body type and her color selection is reminiscent of a Crayola highlighter pack.

Jared Leto: Leto tries really, really hard to be cool (and to be a half-decent actor). He just can’t do it. Between his ever-changing mess of hair and closet of ill-fitting, ugly patterns, it’s no wonder GQ named him its worst-dressed man of the year in 2011. Unfortunately, little has changed. Idiotsville.

Michael Moore: The slovenly blob like existence known as filmmaker Michael Moore is relegated to wearing baggy shirts, hoodies, and other garb that should only be for fourteen year olds playing Call of Duty in their parents basement. Were not sure what we expect from him, but if he could alter his shape, he could start wearing normal clothing. As that will likely never happen, he might be the first person to earn a spot in our Hall of Shame in 2017.

Amy Poehler: One of America’s leading funny ladies didn’t have a great year, opting for ill-fitting gowns that do nothing for her. Maybe her outfits are all a part of one big joke we don’t yet get. Also, she’s just turned into an ass. Right?

Lena Dunham: If you can look at Lena Dunham without projectile vomiting, you have a strong constitution. 2017 will bring us the end of her HBO series Girls, which should have ended after its first outing several years ago. She is essentially the female version of Michael Moore and her leftists ramblings are even worse. In 2016 she posted photos of herself on the can and in a mermaid tale. That alone is enough to place her on the Worst Dressed, a picture is worth a thousand words.


Hamish Bowles: Enjoying a second year on the Best Dressed List, the American editor of Vogue is likely to find himself earning our Lifetime Achievement Award in 2017. Always in evolution, Bowles was BOLD in 2016. We saw a lot of patterns and varying prints, with floral ruling the day most often. But Bowles ability to harness the energy and respect of these bold selections is not something you or I could pull off and thats okay. We watch, we respect, we applaud.

Rufus Sewell: If you have not caught up on The Man in the High Castle on Amazon, Season 2 is now available to live-stream. Last year, we saw Mr. Sewell favor tan and cream colors on the red-carpet and at promotional events. This year his use of dark blues and blacks has been a welcome change of pace. As usual, the English gent remains well-tailored. Daniel Craig should take note of this. Sewell enjoys form fitting cuts, but allows the fabric room to breath.

Paul Feig: His Ghostbuster reboot did not go over well with some, but we thought it was fun. Feig has quite the portfolio, and we particularly enjoy his work on the American version of The Office. Mr. Feig, who spends most of his time behind the camera, does not see that as an excuse to look like a slob. I have always enjoyed his dedication to the double breasted suit and how he leans towards window pane designs in his suit fabric.

Jennifer Lawrence: We always knew she would excel far past her stellar performances in the Hunger Games series. 2016 brought more energy and zing to Lawerences wardrobe. She is so insanely gorgeous, one could argue that shed look good in one of Kayne Wests oversized brown hobo t-shirts and that would be a correct thesis. Veering from 2015 style that was reminiscent of the Mad Men era, we saw many adventurous choices from her this year. Lawerences red dress at the Golden Globes was fascinating.

LIFETIME Achievement Award

Shannon Sharpe:
A visit to the wide shouldered Hall of Fame tight ends closet should be required of every young man entering the NFL. They should know how to not only put together a proper outfit, but also what a properly cut suit looks like. Just because you are making more money than you can count, does not mean you can get away with wearing ANYTHING. Sharpe has always understood that being well dressed not only improves your own self-esteem, it also garners respect from your teammates and colleagues. Sharpe is flashy but reserved at each and every turn, and puts an end to the myth that some pro-athletes muscular build does not allow for them to be comfortable and visually appealing in formal wear. He was already inducted into our Hall of Fame in 2015 and earns a Lifetime Achievement Award this year.

Larry Kudlow: Another 2015 Hall of Fame inductee. Its safe to say that Kudlow has not had a fashion or style slip-up in decades. The conservative economist and CNBC commentator is the whole package, making superb choices across the board. Each element is unique but integrated, you wont see a tie pattern clashing with the suit or shirt. Easily one of the best dressed men on cable television, its no wonder Kudlow has earned our Lifetime Achievement Award.

Ivanka Trump: The next President Trump? Smart, beautiful, and down to earth. Sometimes children of successful titans of industry obsess over designer and price tag, making style a distant third. This has never been the case for Ivanka, who has even developed her own $100 million dollar fashion empire. Last year she was on our Best Dressed list and this year she will be the first person ever in the history of our Best & Worst dressed to earn a Lifetime Achievement Award without already being the the Hall of Fame. First female president in the making ladies and gentlemen, Jackie Kennedy would be proud.

Josh Mankiewicz: He has been on our Best Dressed list many times before and even landed in our Hall of Fame in 2015. In 2016, we watched Mankiewicz expand his pocket square collection and lean towards interesting textured ties. As always, his tailoring is amazing and each piece of his ensemble makes the whole effort stronger, there arent any distractions or weak links. We are honored to give him our Lifetime Achievement Award.


Anthony Scaramucci The SkybridgeCapital co-founder and managing partner is one of several finance guys who are being considered for a top role in President-elect Trumps administration, where he would offer advice on how to jump-start our economy. He is in the same realm of style that people like Larry Kudlow prefer, but needs to make bolder color choices to really take it to the next level. One thing we are impressed by are his knots, as so many simply do not know how to fashion a proper knot.

Onward to 2017, where we will Make America Great Again!



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