Martha Stewart Haircuts That Just Didn't Work For The Icon

Martha Stewart is known for many things. She's an entrepreneur, a self-made millionaire, a convicted felon, and, more than anything, a woman who will not be told what to do or how to live her life. And similar to Anna Wintour, Stewart is also known for having pretty much the same haircut, style, and color for eons.

"I have had the honor and privilege of working with Martha since 1989. For the most part, she's kept with a bob," master colorist at The Salon at Bergdorf Goodman in New York City, Parvin Klein, told Martha Stewart Magazine in 2021, adding that they always balayage her hair. "It's always good to make slight changes to tone and the contrast of highlights to keep the look fresh, but it is always elegant, classic Martha," Klein told the magazine. She even said that clients looking for a blond hairdo will frequently request "Martha's color." 

As her own hairstylist points out, Stewart usually sticks to a variation on the classic bob hairstyle. However, she does switch it up from time to time, and if we dig into Stewart's own archives, she's definitely had a whole slew of other cuts too. Despite Stewart's icon status, some of those looks just didn't work. 

In 2017, Martha Stewart took to the stage at the BottleRock Napa Valley Music and Food Festival. Although Stewart was there to do what Stewart does best — cook — it's hard not to be distracted by this haircut. Is she dipping her toe into the lob haircut trend? Are we looking at a mullet in the making? Or was she simply too busy to get a haircut? It's really hard to tell and doesn't do the icon justice.

Martha Stewart didn't include the date on this blast from the past she posted on Instagram in June 2024. But based on the big jewelry and tans, it looks like it could possibly be from the early 1990s or maybe even the late 1980s — but that's just a guess. Although the haircut is admittedly cute, it's hard to take it seriously. The vibe would better suit a college student than a woman in the midst of building her empire. Had Stewart gone for a super short pixie cut instead, it would have been a power move, giving her more of a don't-mess-with-me vibe.

Although Martha Stewart's very own hairstylist, Parvin Klein, pointed out that Stewart tends to stick to a bob, this is certainly not a bob — nor is it a bob that desperately needs a trim. If anything, it appears to be more along the lines of a shag or even the trendy wolf cut that some celebs were rocking in 2024. Stewart was attending the Comedy Central Roast of Bruce Willis (which aired in July 2019), so having a more cutting-edge look does make sense. Unfortunately, it just doesn't land right on her. 

So, let's just say the cut that Martha Stewart showed off at New York Fashion Week in 2024 was meant to be a lob. If that's the case, great! But it needs a little something extra, because as is, it's a cut that falls flat. Stewart's hair just doesn't have quite enough natural body to give the style the volume it needs. If it had layers to lend some depth and personality, that would be a whole other story, and this haircut likely wouldn't be on this list.

We all know someone that has only ever had a short haircut. Then, when one day they show you a throwback photo where they have long hair, you think to yourself, "Oh, that's why you keep your locks short." Well, that's exactly what we have here. Although Martha Stewart is undoubtedly beautiful with long hair, similar to her long pixie look, it just doesn't fit the mogul we've all come to admire and respect. That Martha Stewart is the one with the forever blonde power bob.