May 30, 2023

Jennifer Lopez wearing a bandana in the early 2000s

It might be safe to say that looking back at photographic evidence of your looks from the 2000s might make you say, what on earth was I thinking? We’re right there with you. However, it is fun to look back on our beauty dos and don’ts from that era with fondness, especially since a few of those trends are making their way back into our lives.

Well, sort of given that we’re now putting a modern, more polished spin on these back in the day trends. From pink hair to an iconic career-changing bob, we have rounded up a list of a few of our favorite hairstyles from the 2000s. We hope you have feelings of nostalgia and potential inspiration while you scroll through these oldies but goodies.

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The Asymmetrical Bob

Rihanna Asymmetric Bob

When Rihanna hit the music scene with a new do and attitude for the debut of Good Girl Gone Bad, the world took notice. The jet black bob crafted by celebrity stylist Ursula Stephen made Rihanna an instant beauty icon.

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Logo Blonde Bob

Lil Kim Logo Hair

Lil’ Kim has and will always be a trendsetter. The beauty chameleon was known for wearing bobs that ranged in color, length, and in this case, design. The Queen Bee’s blonde, Versace logo-adorned bob is a classic.

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Neon Pink Hair

Gwen Stefani with pink hair.

Gwen Stefani is another musician that played by her own fashion and beauty rules. Stefani rocked her bold pink tresses from the late ’90s into the early 2000s with shapeshifting cuts that included bangs and flipped-out bobs.

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Pink Kangoo Hat with Pink Bandana

Missy Elliott Pink on Pink at the Grammy's

Missy Elliot is responsible for my 2000s Kangol hat obsession. Her 2002 Under Construction album release reintroduced a new generation to 80s style, including Adidas tracksuits with Kangol hats to match.

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Twisted Updo

Tia and Tamera

Tia and Tamera were the hair prototype for many girls in the 2000s. Tamera’s twisted updo at the 2000 Soul Train Music Awards—featuring the very on-trend spiky sprays of hair—is one of our favorites.

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Cropped Curls

Keri Russell Cropped Curls

Whether you loved or hated Felicity’s abrupt hair change during season two of the hit WB television show (Keri Russell received death threats), her highlighted cropped curls made a huge impact and showed off Russell’s beautiful features.

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Bold Streaks

Christina Aguilera Bold Streaks

The Dirrty era of Christina Aguilera’s career was controversial (and iconic) as the pop star leaned into Xtina to release her fourth studio album, Stripped. The chunky red clip-in’s alongside the smokey eye looks and chaps cemented her place in pop culture history.

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Fire Red Pixie

Eve Red Pixie

Eve made her musical debut in the ’90s with a short blonde pixie. However, in the 2000s, she heated things up with a red hot pixie. If you want to try this bright color, give hair paint wax a try so you can experiment without a long-term commitment.

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Fringed Shag

Courtney Love Shag Hair

Courtney Love’s cropped shaggy look at the 2000 Golden Globes offers up the perfect mix of grunge and glam.

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Bejeweled Bandana

Jennifer Lopez Bandana

If we took a poll, we imagine this look from the MTV VMAs would be at the top of Jennifer Lopez’s most beloved red carpet looks—which is saying a lot, given just how many iconic moments she’s had.

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Fulani Braids

Alicia Keys Fulani Breads

Who could forget Alicia Keys’ 2001 Songs in A Minor album cover with her beaded braids under a green hat? Fulani braids became her beauty signature, while her talent inspired us all.

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Chunky Red Pixie

Kelly Rowland with chunky red highlights.

Kelly Rowland has always experimented with color and length. Remember her blue highlighted pixie in the Say My Name video? Another one of her most memorable looks was the red highlighted pixie she wore flipped up and in a bob with a bang,

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Two-Toned Cornrows

Beyonce Two-Tone Cornrows

Beyoncé in braids is always a mood. Her highlighted cornrows are still one of the most recreated protective styles around.

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Middle Part with Flipped Up Ends

Gabrielle Union Flipped Ends

Gabrielle Union’s middle-parted flipped style is still a do in my book and is starting to reemerge among those leaning into some of the popular trends from the 2000s. To recreate this look, all you need is a flat iron to bump your ends upward.