20 '90s Bob Ideas That Ooze Coolness and Ease This iconic short cut packs the style. By Calin Van Paris Updated on January 14, 2025 @ 08:44AM Credit: Alexis Duclos / Getty Images Short hair is here to stay. Over the last few years, updated iterations of short styles—think pixies, bobs, and shags—have dominated social feeds and the streets, ushering in a new guard of styles fluid enough to suit all textures. A commonality between them is a desire for movement, volume, and personality, all of which collide in the most memorable ’90s bobs. “French bobs with baby bangs can feel reminiscent of the ’90s; I love a classic bob and bangs, Uma-Thurman-in-Pulp-Fiction style; a preppy bob with wispy bangs is super ’90s,” says hairstylist Lauren Bailey-Chaidez. Face-framing layers, natural texture, all sorts of bangs, and blown-out bounce are all characteristic of a ’90s aesthetic—both back then and very much now. “[Bobs] really signify a new era and are such a timeless versatile hairstyle that are suited for all hair textures,” Thahn Vo tells us. Considering opting for such a chop? Read on for a medley of throwback ‘90s bobs and expert styling tips from Bailey-Chaidez, Vo, and celebrity hairstylist Justine Marjan. Meet the expert Lauren Bailey-Chaidez is a hairstylist and owner of Los Angeles’ Feverfew Salon. Justine Marjan is a celebrity hairstylist and the cofounder of Highlight Artists, an agency representing hairstylists and makeup artists in New York and Los Angeles. Thahn Vo is a hairstylist and makeup artist in Sydney, Australia. 01 of 20 The Meg Meg Ryan. Evan Agostini / Getty Images Bailey-Chaidez cites Meg Ryan’s bob—worn tousled, curled (think City of Angels), and ironed, depending on the occasion—as a quintessential ‘90s cut. This cut toes the line between shag and bob, which makes it an ideal shape for the current beauty climate. That tousled, shaggy texture makes it suitable for almost all hair types. 02 of 20 Natural Curly Lob Tracee Ellis Ross. Ron Galella / Getty Images Tracee Ellis Ross’s natural curls have held their definition throughout her career. The late ‘90s saw the actor rocking a shoulder-skimming cloud of ringlets that showcased the visual power of organic texture. This style has proven timeless as it has cycled back into trends many times since. 03 of 20 Jawline-Grazing Bob Hailey Bieber. Jon Kopaloff / Getty Images “Hailey Bieber’s jawline-grazing bob has been hugely influential and inspired so many others to go short shortly after,” says hairstylist Justine Marjan. “I love that there is also more styling versatility with the shorter length so that people are less intimidated.” Though glossy and glamorous, this cut’s simple center part helps cement its referential ’90s nature. 04 of 20 Ringlet Bob Yara Shahidi. Marc Piasecki / Getty Images As with Ross’s ‘90s bob, Yara Shahidi’s is designed around her natural texture. The rounded iteration features a subtle part at the center, along with a subtle baby bang that plays well within both decades. Her bouncy curls look full and healthy—which is always on trend. 05 of 20 Side-Swept Bob Emma Stone. Pascal Le Segretain / Getty Images More bangs, please. Emma Stone’s bob is comprised of tiered texture and a well-blended curtain bang swooped to one side. It's a pleasing evolution of layered bobs past. 06 of 20 Blunt Bob Bella Hadid. Stephane Cardinale / Getty Images Blunt lines feel relevant both to the ‘90s and now. Bella Hadid’s blunt bob is dramatic and chic, ideal for those wanting a polished chop. Wispy bangs or longer curtain bangs would pair nicely with this structured cut. 07 of 20 The Rachel Jennifer Aniston. Kevin Mazur / Getty Images Jennifer Aniston’s iconic chop created a styling category in its own right, one defined by an assemblage of layers styled to flip out and turn inward. The butterfly and wolf cuts that have defined the last couple of years have led to a resurgence of layering—meaning there’s a place for a reimagined Rachel haircut for the first time in decades. 08 of 20 Razor Bob Zendaya. Michael Loccisano / Getty Images For a look that’s more late ‘90s/new millennium, opt for razored texture, as demonstrated by Zendaya. Jagged fringe is not for the faint of heart. This cut could work for pin-straight lengths and curls if thoughtfully styled. 09 of 20 Air-Dried Bob Laura Harrier. Amy Sussman / Getty Images A little rumple helps a chop exude the ease of ‘90s style. Laura Harrier’s bluntish bob feels both French girl and ‘90s-inspired with a bit of wave and rounded ends. To recreate her look, all it takes is a good old-fashioned air dry. 10 of 20 Crimpy Bob Steve Granitz/Getty Images A crimpy bob is always in style, regardless of your hair texture. Soft curls and rounded baby bangs lend to the vibe while framing the face. Pair the 'do with a lip liner and gloss combo to embody the '90s aesthetic. 11 of 20 Baby Bob Mike Coppola/Getty Images Tyla's short cut gives a nod to '90s Winona Ryder. The actor’s hair edged between pixie, shag, and bob for years. This halfway iteration, a baby bob, skews timeless and elegant. If you don't like spending time styling your hair, the edgy cut is simply unfussy. 12 of 20 Boyfriend Bob Kaia Gerber. Bryan Bedder / Getty Images The ‘90s and now are times of gender fluidity. Kaia Gerber’s curved, glossy, boyish bob is undeniably chic and worthy of recreation. Paired with her fluttery eyelashes and perfect nude lip, the androgynous cut feels modern and daring. 13 of 20 Piecey Lob Kerry Washington. Andrew Toth / Getty Images Lash-grazing, piecey bangs are the main draw of Kerry Washington’s long bob, which also features a collection of soft waves. Whether you have straight hair or lean curly, this undone long bob will flatter many different hair types. Just reach for a curl cream or curling iron accordingly. 14 of 20 Pinned-Back Bob Stephane Cardinale-Corbis/Getty Images Another era-defining cut, the pinned-back bob is a beautiful canvas for styling and accessories. A chic middle part and logo earrings make this style feel modern and dainty—but a side part would look just as good. 15 of 20 Blown-Out Bob Halle Berry. Ron Galella / Getty Images “I love the swing and bounce that styling can add to a bob,” says Bailey-Chaidez. “Think Drew Barrymore’s Guess Jeans ads, or the sort of playful, androgynous styling that harkens back to Calvin Kline CK1 ads.” Halle Berry’s bob is bouncy and sleek—though her natural texture around the time was also something to behold. 16 of 20 Polished Lob Selena Gomez. Steve Granitz / Getty Images A blunt bob, but make it soft. Selena Gomez’s polished lob skims the shoulders with ends turned slightly inward for additional glamour. Also present? The center part is also a signal of ’90s influence. 17 of 20 Curly Bob Audrey Tautou. Toni Anne Barson / Getty Images Audrey Tautou is among the most aspirational of ‘90s French girls, making her myriad chops inherently stylish (we don’t make the rules). This bob provides a chic and easy means of celebrating natural curls. The slight a-line shape helps keep her cut from looking like a triangle. 18 of 20 Undone Bob With Bangs Rihanna. David Becker / Getty Images Curtain bangs and gelled organic texture lend to Rihanna’s bob, a look that’s wholly ‘90s in nature. This cut is all down to the (minimal) styling so be prepared to commit for maximum impact. A good hair gel is key to recreating the subtle wet look. 19 of 20 A-Line Bob Taylor Swift. Anthony Harvey / Getty Images “I’m loving a one-length blunt bob most. It’s so versatile, depending on styling," says Bailey-Chaidez. Taylor Swift’s A-line bob and super blunt bang are all about pin-straight polish. As such, this style is best reserved for naturally straight lengths, the better to save organic texture from any unnecessary damage. 20 of 20 Pixie Bob Keira Knightley. Nadine Rupp / Getty Images Kiera Knightly stepped onto the '90s and Y2K scene with close-cropped hair, her grow-outs providing ample inspiration for similarly shorn styles. This bob is one half pixie with long, wispy bangs and a near-mullet shape that makes it particularly memorable. This cut is great for those with fine hair looking to fake density and thickness. Read more: Beauty Hair