The Trendiest '90s Haircuts For That Retro Sitcom Star Look

As we've seen these last few years, the 1990s are back in a major way. From the Y2K fashion that just won't quit, to the reemergence of the lower back tattoo, to even the musicians who have recently announced tours (Justin Timberlake, anyone?), it feels like 1995 is here all over again. Which, for those who experienced the '90s and loved them and those who weren't quite old enough to really embrace them, is fantastic news.

One of the most exciting trends of the '90s were the hairstyles. Whether you loved or loathed The Rachel, the iconic cut that Jennifer Aniston popularized on "Friends," you certainly know what it is — hence it's forever status. But as much as this cut dominated the headlines in the '90s and still remains at the forefront of hairstyles that all but moved mountains, it's certainly not the only '90s 'do to choose from if you're looking to lean into this current Y2K trend. Whether you want to relive a haircut you had back in the day and loved, or pay homage to a certain actor or character with a hairstyle you're finally courageous enough to try, there's certainly a trendy '90s haircut for you.

Originally popularized by Rachel Green, this face-framing cut has been reinvented easily a dozen times since the 1990s. In fact, even Jennifer Aniston herself breathed new life into the classic style when she showed up to the 2024 Golden Globes.

Of course, asking for The Rachel is an easy haircut to request from a stylist, because everyone knows that it is. But while that's true, it doesn't mean not every type of hair is going to work for it. "The Rachel [haircut] works best on hair with a lot of layers as it will give your hair more body by surrounding your face in a heart shape and framing it perfectly," hairstylist Luke Williams tells Real Simple. It also helps if your hair has natural fluffiness to it or if you're able to keep it on the fluffy side by washing it often, so it falls perfectly.

Although Winona Ryder was never on any sitcoms in the 1990s, sticking to only movies, the pixie cut that she rocked through most of the decade and in various lengths will always have an important place in hair trend history. "The pixie cut has been an iconic style throughout the years," hairstylist George Northwood tells British Vogue. "It's now very of the moment once again... Personally, I'm a fan of the '90s take on the pixie — think Winona Ryder and Princess Diana — who both had very wearable versions with a slightly longer fringe and more texture."

Like asking your stylist for The Rachel, the pixie cut is also a pretty straightforward request. However, your hair texture and thickness will play a role in how your stylist will go about giving you the best pixie for your hair type.

As the shortened version of the "flipped bob," the flob is a high-volume style that wasn't just a mainstay on the runways in the 1990s (think Cindy Crawford and Christy Turlington), but was popular amongst mere mortals too. "The flob cut has the line and length of the bob but the top layers have much more texture, so it's lighter on top and easier to flip around," celebrity hairstylist Marc Mena tells Glamour, adding that a regular bob when flipped can feel a bit heavy, so it's the layered top that makes all the difference. "The flob is cut and parted all around — in the middle, on the left, and then the right — so the ends are just texturized and it gives the hair movement," says Mena. These days we're seeing the flob again on actresses like Zendaya and Aubrey Plaza, and it's still just as every bit as fun as it was in the 1990s. It's also giving serious mob wife aesthetic vibes. 

Princess Diana was only 36 when she died in that tragic car accident in Paris in August of 1997, but her impact on the world will last forever. Not to reduce her to just a fashion icon, because she was so much more than that, we still need to recognize the fact that Princess Di nailed it when it came to trendsetting.

"Diana has always been a style icon and the bob never goes out of fashion," artistic director Suzie McGill tells Glamour UK. "Diana always sported a bob, sometimes hitting just past her cheekbones and sometimes slightly longer at the back, but what was always a statement look of Diana's bob was the deep side parting and the volume and layers within her hair." It's those layers that immediately take the classic bob to a whole other level. As much as it's beautiful and trendy, if you ask your stylist for it, remember that while layers always look good, they can be quite challenging when you try to grow them out.

Although these days we've seen the blunt bob cut on everyone from Bella Hadid to Hailey Bieber, there's someone who popularized it even before them: the one and only Britney Spears. At the height of her career, one of the many hairstyles that Spears rocked was the blunt bob and, despite the fact that it was a look that had been around for quite a long time already, she certainly made it her own.

When asking for the blunt bob, in addition to showing your stylist a photo of Britney just because, make sure to talk about what length is best for the bob based on your hair texture. For example, straight hair that's medium thick is going to call for "invisible layers in the back," as hairstylist Andy Lecompte tells Brydie. While "if you have thick, curly hair, it's best to keep the length around your collarbone," says Lecompte.

When it came to covetable curls in the 1990s, you didn't need to look further than Hilary Banks' glorious locks on "The Fresh Prince of Bel Air." For six seasons, Parsons' beloved character wowed audiences with not just her style, but her ability to steal pretty much every scene. While the 1990's classic series has been off the air for almost 30 years, those curls remain just as trendy as every (think Kerry Washington at the Sundance Film Festival last month), because natural curls never got out of style. 

"If it's curls all the time, a lot of shape and releasing excess weight can enliven your curls to new heights," hair stylist Jonathan Van Ness tells Elle UK. "I always recommend consulting with a stylist who specializes in curly cuts about what will work for your lifestyle and aesthetic." There's no one type of curl so, as Van Ness points out, a specialist is really going to be your best bet.