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This Fashion Trend Makes You ‘Look Rich,’ According to a Celebrity Stylist

He also warns men to avoid a certain summer footwear trend.

Celebrity Styles

Photo Illustration by Victoria Sunday/The Daily Beast/Getty Images

Are flip-flops OK to wear to dinner? Does pairing your suit with sneakers look way too casual, or casually cool? And how can a simple color combination make you “look rich”?

As trends come and go, it can be difficult to keep up—unless you have a world-renowned guide like Law Roach, a celebrity stylist and Project Runway judge who does not follow trends; he sets them.

Roach, who grew up in Chicago and now lives in Los Angeles, has a sharp eye and rich historical expertise that has made him the sought-after stylist for A-listers like Céline Dion, Kerry Washington, and Ariana Grande.

Law Roach is a celebrity stylist and a judge on “Project Runway.”

Law Roach is a celebrity stylist and a judge on “Project Runway.”

Disney

Often referred to as the “Image Architect,” the 47-year-old has a masterful, borderline prescient approach to red-carpet fashion that has helped turn Spider-Man star Zendaya into a style icon whose ensembles go viral time after time.

Following his appearance on Obsessed: The Podcast, Roach shared his unfiltered thoughts on the current trends—Law’s laws, if you will—he’s obsessed with, and those he is far less enthusiastic about, with the Daily Beast.

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Kitten Heels

Law Roach said he calls kitten heels “the Michelle Obamas” after the former first lady. Pictured here with Barack Obama in August 2013, and on stage in August 2025.

Law Roach said he calls kitten heels “the Michelle Obamas” after the former first lady. Pictured here with Barack Obama in August 2013, and on stage in August 2025.

Aude Guerrucci/Pool via Getty Images;Arturo Holmes/Getty Images

Kitten heels can be a comfortable yet fashionable alternative to higher pumps, but Roach shared some guidelines to keep in mind.

“I think there is a time and a place,” he said, adding that the pair should have a closed, pointy toe for it to be “chic” and “sophisticated.”

“We like to call them ‘the Michelle Obamas,’” Roach revealed with a laugh. “Even though she’s not wearing kitten heels that much anymore, that’s what we nicknamed them.”

Flip-flops on the street

Jennifer Aniston in New York City in 2013, and Alexander Skarsgård at the Sundance Film Festival in January 2026.

Jennifer Aniston in New York City in 2013, and Alexander Skarsgård at the Sundance Film Festival in January 2026.

NCP/Star Max/FilmMagic;Dia Dipasupil/Getty Images

Flip-flops have slowly made their way from beachwear to beyond. In 2026, multiple male actors attended industry events wearing the toe-baring shoe.

True Blood actor Alexander Skarsgård wore Valentino flip-flops on the red carpet of the Sundance Film Festival, and Wicked actor Jonathan Bailey attended a photo call for Jurassic World Rebirth in London wearing designer flip-flops by The Row.

Roach said he was not a fan of the controversial shoe choice outside the beach.

“Especially on boys. I don’t wanna see boy toes when it’s not necessary,” the celebrity stylist said.

Peplums

Kate Hudson at the 98th Oscars and Rachel McAdams at the Hollywood Walk of Fame, both pictured in January 2026.

Kate Hudson at the 98th Oscars in March 2026 and Rachel McAdams at the Hollywood Walk of Fame in January 2026.

Jamie McCarthy/Getty Images;Mario Anzuoni/Reuters

“Peplum is debatable,” Roach said about the controversial silhouette.

“I think certain body types could really benefit from a peplum because it gives the illusion of a hip and a smaller waist.”

Sneakers with a suit

Robert Downey Jr. speaks during CinemaCon in 2026, wearing a metallic green suit and sneakers, and David Beckham arrives at “Good Morning America” in 2024 wearing a tan suit with white sneakers.

Robert Downey Jr. on stage during CinemaCon in 2026 and David Beckham arriving at “Good Morning America” in 2024.

David Becker/Getty Images;Jose Perez/Bauer-Griffin/GC Images/David Becker/Getty Images;Jose Perez/Bauer-Griffin/GC Images

For sneakers with a suit, Roach only offered a two-word comment: “Not obsessed.”

Skinny jeans

Shailene Woodley wears skinny jeans and flats on the set of “Count My Lies” in 2026, and Reese Witherspoon leaves her office building in Beverly Hills in 2015 wearing skinny jeans and red pumps.

Shailene Woodley on the set of “Count My Lies” in 2026, and Reese Witherspoon in Beverly Hills in 2015.

XNY/Star Max/GC Images;Bauer-Griffin/GC Images/XNY/Star Max/GC Images;Bauer-Griffin/GC Images

“I think skinny jeans are never gonna go anywhere. They’re kinda like termites,” Roach said with a laugh.

Adding, “You try to get rid of them when they come back again... but I don’t really mind skinny jeans in certain contexts.”

Oversized suit jackets

Gwyneth Paltrow arrives at Milan airport during the Milan Womenswear Spring/Summer 2026 Fashion Week, wearing an oversized black blazer in 2025 and Cate Blanchett attends the world premiere of “The Lord of the Rings: The War of the Rohirrim” wearing an oversized tweed blazer in 2024.

Gwyneth Paltrow arriving at Milan airport for Milan Fashion Week in 2025, and Cate Blanchett at the world premiere of “The Lord of the Rings: The War of the Rohirrim” in 2024.

Isabel Infantes/Reuters;Andrea Cremascoli/GC Images via Getty Images

The oversized suit jacket has slowly transformed from a trend into a staple, but Roach felt divided about the style.

“I’m in the middle because we’ve seen it for so long, but I think in the right variation at the right place, it could be cool,” he said, adding that he was currently more into a well-tailored look.

Naked dresses

Doja Cat and Kylie Jenner at the 2026 Met Gala.

Doja Cat and Kylie Jenner at the 2026 Met Gala.

Arturo Holmes/MG26/Getty Images;Jamie McCarthy/Getty Images

“The naked dress is very controversial for me because I really felt a certain type of way earlier in my career about the naked dress." Roach said, adding, “I thought it was just unnecessary.”

But with time, his opinion has evolved.

“I do think when it’s done really, really well, and it’s not naked just for the sake of being naked or shock value, it works,” Roach said.

T-shirt dresses

Zendaya attends the "Spider-Man: Brand New Day" Photocall at UGC Cine Cité Bercy on June 24, 2026, in Paris, France.

Zendaya attends the "Spider-Man: Brand New Day" Photocall at UGC Cine Cité Bercy on June 24, 2026, in Paris, France.

Stephane Cardinale - Corbis/Corbis via Getty Images

Some of the trends Roach was a big fan of included statement belts, capris, and T-shirt dresses.

On June 24, Roach styled Zendaya in a black Spiderman T-shirt with no bottoms for a red carpet in Paris.

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Roach said he was “obsessed” with the look.

“I think this is a new trend that we’re gonna see a lot of, and it didn’t happen on purpose. It was kinda accidental the way that this shaped up,” he revealed.

Roach explained that the outfit, which he described as “really cool,” was not the original plan, but came together due to the historic heat wave in France.

“It was 105 degrees in Paris,” he explained. “Let’s just throw the T-shirt on with the pumps.”

Law Roach attends the pink carpet wearing a monochrome gray suit for the 2025 Victoria’s Secret Fashion Show, and Jessica Chastain attends the Zimmermann Womenswear Fall/Winter 2026-2027 show wearing a monochrome orange blazer and outfit in 2026.

Law Roach at the 2025 Victoria’s Secret Fashion Show and Jessica Chastain at the Zimmermann Fall/Winter 2026-2027 show in monochromatic outfits.

Kylie Cooper/Reuters;Pierre Suu/Getty Images

Monochromatic separates

Roach also pinpointed two styles he personally enjoys wearing.

“I wore a monochrome look yesterday. I love it. I think it’s sophisticated, and I think it always makes you look rich,” he said.

Sharon Stone walking the runway during the Vetements Menswear Spring/Summer 2027 fashion show at Paris Fashion Week, and Law Roach at the Actor Awards in March 2026.

Sharon Stone walking the runway during the Vetements Menswear Spring/Summer 2027 fashion show at Paris Fashion Week, and Law Roach at the Actor Awards in March 2026.

Victor VIRGILE/Gamma-Rapho via Getty Images;Caroline Brehman/Reuters

Shoulder pads

Another trend Roach approves of is shirts with shoulder pads.

“I am obsessed with shoulder pads,” he said. “I actually went shopping, and I bought some just button-down shirts that have shoulder pads. I think it’s really cool and it gives a nice proportion.”

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