20 '90s Bob Ideas That Ooze Cool and Ease

Short hair is here to stay. Over the last few years, updated iterations of short styles — think pixies, bobs, and shags — have dominated 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…” muses hairstylist Lauren Bailey-Chaidez. “I’m loving a one-length blunt bob most. It’s so versatile, depending on styling.” 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. “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.”

Related: '90s Hairstyles That Are Back and Better Than Ever

Another easy nod to the ‘90s? A slick center-part, as demonstrated by the likes of Hailey Bieber. “Hailey Beiber’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.” And that’s a good thing — bobs are, after all, ideal markers of new beginnings. “It really signifies a new era and is such a timeless versatile hairstyle that is suited for all hair textures,” effuses hairstylist Thahn Vo.

• Lauren Bailey-Chaidez is a hairstylist and owner of Los Angeles’ Feverfew Salon.

• Justine Marjan is a celebrity hairstylist and global stylist for TRESemmé that works with Khloe Kardashian and Ashley Graham.

• Thahn Vo is a hairstylist and makeup artist in Sydney, Australia.

Considering opting for such a chop? Read on for a medley of throwback ‘90s bobs and coveted looks of today to inspire your next salon appointment.

The Meg

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.

Center-Part Bob

As noted by Marjan, Hailey Bieber’s bob has aided the cropped renaissance. Though glossy and glamorous, this cut’s simple center part helps cement its referential ’90s nature.

Curly Chop

Tracee Ellis Ross’ 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.

Ringlet Bob

As with Ross’ ‘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.

Side-Swept Bob

More bangs, please. Emma Stone’s bob is built of tiered texture and a well-blended curtain bang swooped to one side, a pleasing evolution of layered bobs past.

Blunt Bob

Blunt lines feel relevant both to the ‘90s and now. Bella Hadid’s blunt bob is dramatic and chic, an ideal choice for those wanting a polished chop.

Related: 20 Blunt Cuts for Every Face Shape and Hair Texture

The Rachel

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 that there’s a place for a reimagined Rachel haircut for the first time in decades.

Razor-Bang Bob

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, but, if thoughtfully styled, this cut could work for pin-straight lengths and curls alike.

Bouncy Bob

Drew Barrymore’s bouncy bob helped to embody her elevated flower child aesthetic—with or without the daisies. Soft curls and rounded baby bangs lend to the vibe while framing the face.

Air-Dried Bob

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 courtesy of a good old-fashioned air dry.

Baby Bob

One cannot discuss ‘90s beauty without mentioning Winona Ryder. The actor’s hair edged between pixie, shag, and bob for years, and this halfway iteration, a baby bob, skews timeless and elegant.

Boyfriend Bob

The ‘90s and now are times of gender fluidity. Kaia Gerber’s curved, glossy, boyish bob is undeniably chic and worthy of recreation.

Pinned-Back Bob

Another era-defining cut, Cameron Diaz’s blonde bob was snipped to graze her cheekbones, making it a beautiful canvas for styling and accessories. Deep side parts and barrettes helped to make Diaz’s style a standout one.

Piecey Bang Bob

Lash-grazing, piecey bangs are the main draw of Kerry Washington’s long bob, which also features a collection of soft waves.

Blow-Out Bob

There’s nothing quite like a rounded blowout to call the ‘90s to mind. Halle Berry’s bob is bouncy and sleek—though her natural texture around the time was also something to behold.

Related: How To Give Yourself the Perfect Silky Blowout When You Can't Visit the Salon

Polished Bob

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.

Curly Bob

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.

Bob With Bangs

Wispy, blown-out 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.

Blunt Bangs Bob

Another Y2K cut, 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.

Pixie Bob

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, wisped bangs and a near-mullet shape that makes it particularly memorable.

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