7 Pics Of Sherri Shepherd's Worst Outfits That Prove She Desperately Needs A New Stylist
Popular TV host Sherri Shepherd has had a stunning transformation and been in the entertainment industry for decades. And along with her interesting opinions on her talk show, "Sherri," or her acting performances, one thing a lot of fans like to talk about is her fashion.
Shepherd has been working with stylist Willie Sinclair III for years, with the stylist putting together her talk show outfits and more. In late 2025, Sinclair showed off Shepherd's many New York Fashion Week looks that he styled. He wrote on Instagram, "You know we have to turn up the heat when Sherri hits the streets." While there have been a lot of great and fashionable ensembles over the years, including a few from Shepherd's first NYFW appearances, there have also been plenty of misses. So much so, that Shepherd may need to try a new stylist soon.
So what were the worst fashion looks for Shepherd? Here are some of the biggest style mistakes that we think she should've nixed.
Shepherd's all-pink look was too in your face
For one event, Sherri Shepherd decided to go for a bright pink look. And while she can definitely pull off the bright color, this outfit simply had too much of it.
With the sleeveless pink dress with a scalloped hem, a small bright pink purse, and strappy pink heels with studs on them, it was just way too pink for one night out. To make it better, the outfit definitely would've benefitted from having another color mixed in somewhere.
The TV host's holiday look was all over the place
Sherri Shepherd got all dressed up to go to a celebration for Macy's Thanksgiving Day Parade in 2024 in New York City. But by just looking at her outfit, you couldn't tell where she was headed.
The ensemble was all over the place. It featured a bright pink long coat with a fur collar and cuffs. This was paired with a gold sparkly shirt, black jeans, and sneakers. Sure, the jeans and sneakers were probably comfortable, but they didn't match the holiday vibe at all.
A long plaid shirt was a major miss for Shepherd
The former "The View" host went for a more casual look for a stand-up routine in Atlanta, Georgia, in 2024. But what should've been a simple, relaxed outfit was even stranger than some things she wore on her TV show.
Sherri Shepherd had on what looked like a long black jumpsuit, or a black top and pants. She then adding a long multicolored plaid shirt on top that covered the entire 'fit and knee-high cream boots. The black base and plaid overshirt made Shepherd look completely shapeless, and the bold colors of the shirt made the outfit even worse.
An awards show dress had Shepherd looking like a pom pom
In 2024, Sherri Shepherd had a big night when she won the award for Outstanding Host in a Talk or News/Information (Series or Special) at the 55th Annual NAACP Image Awards. For the awards show, she donned a gold dress and metallic heels that fit the vibe of the night, but the design of the dress itself was a big fail.
The dress featured tassel-like pieces all over, continuing into a high neckline. Altogether, it had Shepherd looking like a pom pom. And with all the pointy pieces, it even looked a little dangerous.
Shepherd's abstract dress drew attention for the wrong reasons
While attending the Daytime Emmy Creative Arts and Lifestyle Awards in 2023, Sherri Shepherd and her stylist went for an abstract and colorful look. But the dress really didn't work. It had stripes all over in orange, highlighter yellow, black, blue, and more.
The biggest issue with the dress was arguably the oddly placed circles at the front, which caught people's attention for all the wrong reasons. Without this detail, the dress wouldn't have been so bad. But as it was, it didn't work.
Odd cutouts and bright orange didn't work for the TV star
During a visit to SiriusXM studios in NYC in 2023, Sherri Shepherd's monochromatic look was a big fashion fail. The star posed for photos in an all orange look, with the outfit giving off a bit of a Velma from "Scooby-Doo" vibe.
That's not necessarily a bad thing. But what really ruined the outfit were the strange cutouts on the top's lower sleeves and under the neckline. They just felt totally out of place and looked odd on Shepherd.
Shepherd's white and feathered ensemble raised eyebrows
Sherri Shepherd is unafraid to try edgy and unexpected outfits. And while she sometimes pulls them off, other times, it's not worth the risk. In this case, Shepherd tried out a white and lilac purple outfit with a jacket, skirt, and boots.
The color combo wasn't the issue, with the hues looking great on her. But details like the feathery embellishments on the skirt and the boxy shape of the boots were odd, both alone and put together as a full outfit.