Glam's Favorite Celebrity Hair Moments From The '90s

The '90s introduced some truly wonderful and truly wacky hairstyles, some of which you'll be seeing everywhere. While some of these trends were embarrassingly regrettable (we're looking at you, mall bangs!), others were so chic they're making a comeback among today's celebs. A-listers including Bella Hadid, Dua Lipa, Billie Eilish, and Kim Kardashian have all rocked seriously '90s-inspired 'dos lately. Even some of those '90s trendsetters themselves, such as Jennifer Lopez, have recently brought back looks they haven't worn in nearly three decades.

Since it's clear that the '90s aesthetic is back, at least for a little while, Glam dug through the internet archives to unearth some of the best (and worst) celebrity hair moments of the time. If you're looking for some inspiration for your take on '90s hairstyles or just some cringeworthy laughs, follow us on this journey as we remember our favorites from the decade of sometimes amazing, sometimes awful, but always unforgettable hair.

No hairstyle is more emblematic of the '90s than "The Rachel," a multi-layered lob with highlights galore. The 'do was named after Rachel Green, Jennifer Aniston's character from "Friends," and when she debuted the cut on the show, women everywhere ran to their stylists to get the look. As Chris McMillan, the celebrity stylist who created the haircut, shared with Hello! Magazine, "I told her she should grow her fringe out, get some highlights ... We cut the length and added all in these layers to blend the bottom to the bangs," he said, "and the rest is history."

For the entire decade of the '90s, Jennifer Aniston and her alter ego, Rachel Green, were pretty much #hairgoals. In addition to "The Rachel," Aniston's messy buns held together with a variety of chunky claw clips became a go-to look. The style was simple but chic, and it taught us all how invaluable a good claw clip is, especially when you have to leave the house in a hurry.

For Black women and girls of the '90s, Brandy's signature braids were the equivalent of "The Rachel." In an essay for Stylist, Leah Sinclair explains that, in "a sea of whiteness," Brandy's braids showed that Black hair is just as beautiful and trendy as white hair. This was a powerful message, since Black girls and women had long been encouraged to make their hair conform to white beauty standards.

Big, poofy hair was emblematic of the '80s, but Cindy Crawford successfully updated big hair to make the style sleek enough for the '90s. Instead of opting for lots of volume on the top, Crawford's classic '90s look created volume all over mixed with perfectly placed, subtle waves. In fact, she revealed that old-school velcro rollers were the secret behind her enviable volume. "I love Velcro rollers because I find them foolproof," she told Coveteur. "It's very hard for me to get tension on my hair when I'm blow-drying it with a round brush."

Madonna became a style icon when she exploded onto the music scene in the early '80s, and she continued to shape high fashion throughout the '90s. When she rocked an ultra-high, clip-on ponytail during her Blond Ambition tour, Madonna started yet another massive trend, with Warner Bros. Records VP Liz Rosenberg telling People in 1990, "Lots of women – and men – are showing up at her concerts with this hairdo. It's really catching on." Ponytails everywhere moved from the back of the head to the top, often held in place with an ostentatious scrunchie — here are a few scrunchie hairstyles that'll take you back.

Lisa Bonet, a.k.a. Denise Huxtable on "The Cosby Show," showed America what it looked like to be unapologetically Black, rocking her natural hair throughout the show. During the third season, dreadlocks became her signature look and has ever since. As Dorcas Siwoku points out in an essay for Unruly, Bonet never felt the need to conform to Hollywood's beauty standards, always opting for her own sense of style. In fact, her daughter, Zoe Kravitz, shared with Asos (via HelloBeautiful), "She is the most true artist I have met. She doesn't change for anybody."

When Lisa Bonet left "The Cosby Show" to star in "A Different World," we all met Cree Summer and gained another natural hair inspiration. In an interview with Curly Nikki, Summer revealed that her hair has always been au naturel, which is rare for Black women in Hollywood. Though she wasn't a fan of her mass of curls back then, Summer was delighted that her all-natural style inspired many to embrace their own. In fact, it wasn't until after she left "A Different World" that she "fell in love with" her hair.

Drew Barrymore embodied "it girl" in the '90s. She solidified her ultra-cool status when she chopped her hair at the beginning of the decade. The ear-length bob gave her an edgy, but sweet, aesthetic that fit her perfectly. Eventually, Barrymore added blunt baby bangs to her bob, which became her signature look — one replicated by countless women and girls throughout the decade.

The legendary Barbra Streisand kicked off the crimped hair trend, which persisted into the '80s, thanks to pop stars including Cindy Lauper. In the late '90s, Christina Aguilera brought crimped hair back, and we all followed her lead. Remember spending hours with a hot crimping iron or putting dozens of braids in wet hair so those zig zags would appear when you took them out in the morning? We do.

When Jennifer Lopez hit the scene in 1990, her natural curls were on full display. As Johanna Ferreira explains in Mamas Latinas, Latinas have often straightened their natural curls to fit the expectations of American beauty. At the beginning of her career, Lopez was a proud Latina, unafraid to rock her natural curls. We love to see it!

Our '90s queen, Britney Spears, single-handedly made braided pigtails cool when she wore them with her iconic schoolgirl outfit in the "Baby One More Time" video. And, since pretty much every girl in America did whatever Britney did back in the mid-to-late '90s, braided pigtails became the hot hairstyle for a minute.

But before Britney made braided pigtails cool, Spice Girl Emma Bunton took pigtails from the schoolyard to the red carpet as Baby Spice. Her signature high pigtails became the go-to hairstyle for all girly-girl teeny boppers because the look created a perfect balance between innocent sweetheart and sexy superstar.

Before Missy Elliott, finger waves — gelled, S-shaped waves in short, slicked-back hair — were associated with Old Hollywood glamour. But Elliott made the style synonymous with '90s hip hop, celebrity stylist Chuck Amos told Fashion Magazine. When she rocked the style in her music videos, the rest of the '90s hip-hop elite followed suit, cementing the trend that's still popular with Black women. "Foxy Brown, Lil' Kim, TLC—all the girls of that era were doing it," he said.

Winona Ryder wasn't anything like the other Hollywood "it girls" of the '90s. She was weird, but in a good way, which made her a patron saint of weirdos everywhere. When she absolutely slayed a messy pixie cut, the style immediately became the look for anyone looking to express their alternative aesthetic. Eventually, the cut made its way into the mainstream, becoming one of the iconic looks of the decade.

No one really knows how the '90s butterfly clip trend started, but we do know that at some point in the late '90s, everyone had butterfly clips in their hair. They even became a red carpet accessory, with superstars such as Tyra Banks, Drew Barrymore, and Kirsten Dunst adorning their formal updos with the adorable clips.

The '90s were an incredible decade for Black fashion. But, arguably, the boldest statement in '90s Black fashion were the head wraps sported by singer Erykah Badu. As Iris Cuppen writes for Diggit Magazine, Badu's unique, Afrocentric style became "a radical symbol of [B]lack femininity in the male-dominated world of R&B and – more importantly – hip hop." Badu was a proud Black woman who wasn't going to shy away from that.

Each of the Spice Girls made their unique contribution to '90s fashion. Baby Spice's contribution was her iconic pigtails, while Ginger's were those chunky, blonde highlights that perfectly framed her face. When the trend was adopted and adapted by teen royalty of the early 2000s, including Lindsay Lohan, Kelly Clarkson, and the Olsen twins, chunky highlights became the dye-job everyone requested.

"Baywatch" star Pamela Anderson was the definition of sex appeal in the '90s, and her blonde messy updo was the epitome of glam. It even got its own name: the Pammy Updo. We all tried, with varying levels of success, to nail this look for school dances and weekend nights out. Now, the look is coming back with a vengeance, with icons such as Cardi B and Kim Kardashian recreating the Pammy Updo.

Entire books have been written about the impact "Clueless" had on '90s fashion. Just one impact was making headbands one of the decade's hottest accessories. Though headbands have been popular in nearly every decade since the '20s, the style favorite changes regularly. In the mid-'90s, Cher and Di popularized thick, fabric headbands in every color of the rainbow.

"No Doubt" frontwoman Gwen Stefani's punk, rave-inspired look was copied by millions who wanted to show how different they were from "those other girls." One of her signature, quirky hairstyles was dubbed "space buns" — two buns on the crown of the head. The style was so easy and interesting that it caught on immediately.

When Halle Berry emerged on the scene in the early '90s, she already had the unique pixie cut she'd sport throughout the decade. Her short, sometimes curly style was distinctly different from many starlets of the time, and, as Us Weekly reported, Berry credits the style for her success. She believes her unique look, which made her feel "like my best self," caught the eye of casting directors, giving her the edge when competing for her early roles. "I had no hair to hide behind, it was just all me," she explained.

Blunt, severe cuts were all the rage when it came to '90s hair, and no style represents this better than the legendary bob paired with baby bangs that Uma Thurman sported in "Pulp Fiction." As celebrity stylist Sally Hershberger told the Observer, baby bangs are more "like a piece of art" than a hairstyle. Those who rock them immediately stand out, which is why the bangs caught on after Thurman debuted them.

The explosion of hip hop in '90s pop culture forever changed fashion. Trends that were popular in Black and Latino communities for years made their way to mainstream fashion through hip-hop stars such as Aaliyah. When the late singer started rocking a triangle bandana over her tresses, it wasn't long before all the white teen queens were doing it, too — including us.

Raise your hand if you ever burnt your forehead with a curling iron trying to replicate D.J. Tanner's signature bangs! These poofy, round bangs were dubbed "mall bangs" after all the teen mallrats who rocked them. They were a remnant from the sky-high teased hair of the '80s, and D.J., played by Candace Cameron Bure, brought them to a whole new generation. Luckily, this trend died in the '90s and has actually stayed dead. We just couldn't help but look back at this long-gone look.