25 Trendiest 2000s Fashion Looks to Dress Like A Millenium Pro (2024)

Influenced by the decades of Hip-Hop, Grunge, and Rock fashion styles infused with Emo vibes and Y2K style logomania, the 2000s fashion has a distinguishable look.

Driven by reality show stars and music celebs like Paris Hilton, Britney Spears, Lindsey Lohan, and the Olsen twins, the 2000s has some of the most outrageous looks that continue to inspire fashion designers and fashionistas alike.

In this article, I’ll introduce you to the 25 trendiest garments, footwear, and accessories of the 2000s fashion era that you can shop for and create your authentic outfits and looks right now.

1. Pocketless Low-Rise Jeans

The pocketless jeans trend was when low-rise jeans were the decade’s must-have denim style.

Without pockets, you could achieve the illusion of a butt lift and draw even more attention to your derriere.

Moreover, with flip phones being one of the 2000s’ most significant fashion accessories, pocketless jeans were ideal for showcasing your smartphone.

Would you dare to style it like Christina Milian with a visible white thong on the show?

2. Juicy Couture Tracksuits

If you’re an athleisure fan, you should thank the early Juicy Couture tracksuits for making today’s athleisure clothingsuccessful.

With their Juicy Couture tracksuits and oversized Louis Vuitton bags, Paris Hilton and Kim Kardashian stand out as two of the most representative celebrities of the 2000s fashion.

The style was so iconic that the pair were commissioned to recreate it for a recent SKIMS shapewear campaign.

And now, with 2000s fashion looks back in vogue, Juicy Couture is also returning as a fashion and pop culture icon.

3. Wedge Mules & Platform Sandals

In the 2000s, most footwear was designed to add an extra few inches to one’s height.

Designer brands like Christian Louboutin and Yves Saint Laurent had us falling head over heels for wedges and platforms.

Wedge mules and platform sandals, in that characteristic 2000s look, are ideal if you want to ‘tower over’ your friends.

Above all, as the 2000s platform sandals can be used from spring to late into autumn, wear them for extra height and a lovely summer chic look.

4. Colored Skinny Jeans

With denim being the staple of that era, it is no surprise that skinny jeans became available in every color under the sun.

Whether you were a True Religion, Diesel, or Sevens fan in the 2000s, you must have owned at least one pair of brightly colored skinny jeans.

Few fashion trends united the menswear and womenswear in 2000s fashion more than the brightly colored skinny jeans, but designers focused more on jewel-tone colors instead of pastel colors.

5. Baguette Shoulder Bags

The 2000s baguette shoulder bags were the perfect size for a lip gloss, mirror, keys, and flip phone.

The 2000s fashion years are also the origin of logomania in designer handbags, as no outfit was complete without a logo bag on your arm.

The baguette shoulder bag rose in popularity as a mini-bag style with an entry-level designer price tag.

While shoulder bags like Louis Vuitton’s Pochette were a celebrity must-have, brands like Coach and Dooney & Bourke became famous for launching baguette bags at far more attainable price points.

6. Baby T-shirts and Tank Tops

One stylistic aspect that united most 2000s hip-hop fashion looks was the figure-hugging silhouettes.

As athleisure wear became one of the prominent 2000s fashion trends, it’s no surprise that these closet staples appeared everywhere, from the red carpet to coming-of-age movies.

Often seen in the Friends TV series or worn by the 2000s Disney stars like Alyson Michalka, Ashley Tisdale, and Hilary Duff, baby t-shirts and tank tops were also excellent for showing off your fresh spray tan and midriff.

Those who wanted to showcase a more modest look would wear baby t-shirts under their tank tops.

7. True Religion Bootcut Jeans

True Religion was one of the biggest clothing brands of that decade, often regarded as an icon of the 2000s fashion.

The classic True Religion bootcut jeans became popular in the 2000s to the point where the trousers were considered a status symbol, along with Juicy Couture’s velour tracksuits.

Wore by Destiny’s Child, Jessica Simpson, and Kanye West, True Religion’s horseshoe stitching acted as a ‘coolest people club’ membership card anywhere you went.

8. Capris Pants

Leighton Meester got her ‘big break’ in the 2000s by playing Gossip Girl’s Blair Waldorf.

Nowadays, while Blair’s looks are all over Pinterest boards, not many people know that Leighton is a 2000s fashion icon and influencer in her own right.

Leighton’s love for capris pants and crop tops with wedge heels inspired red-carpet celebrities such as Fergie, Alicia Keys, Rihanna, and Jennifer Lopez.

9. Peep-Toe Pumps and Ripped Jeans

There’s no faster way to step back into 2008 than a pair of peep-toe pumps.

One of the most unforgettable looks of 2000s fashion, Christian Louboutin’s peep-toe pumps with ripped jeans made it to the history books.

Eventually, the peep-toe pumps with ripped jeans became a signature look that made it to hip-hop fashion on and off the red carpet.

10. Wide Stud Belts With Double (Or Triple!) Grommet

There’s no better match to a pair of low-rise jeans than the wide stud belt.

Another 2000s fashion invention, the wide stud belt with double grommet, conferred the wearer with a rockstar chic twist.

Nowadays, nothing screams “2000s celebrity” more than styling your colored skinny jeans with a triple grommet studded belt.

11. Dresses Over Jeans

One 2000s fashion trend that continues to influence streetwear style is wearing dresses over jeans, inspired by the same era’s ‘dresses over leggings’ looks.

Popularized by younger celebrities like Kelly Clarkson, dresses over jeans became a 2000s fashion trend, allowing stars to look dressy without being too formal.

Also, the dresses over jeans 2000s style signaled the start of first looks that began to blur gender lines with a rebellious feel.

12. Trucker Hats

As another 2000s fashion look, we can thank Paris Hilton for leaving behind; trucker hats were quickly adopted by hip hop fashion lovers, appealing to all, women, men, and genderless.

Ed Hardy and Von Dutch launched some of the most popular 2000s trucker hats, fast becoming ‘going out’ staple for all.

Trucker hats were considered one of the chicest accessories of the 2000s and, in their simplicity, worked wonders with t-shirts, jeans, or mini skirts.

13. Belts with Names

One of the most unique 2000s fashion looks was Carrie Bradshaw’s iconic name necklace.

Played by Sarah Jessica Parker, Caroline Bradshaw, the fictional character in HBO’s Sex and the City franchise, wore a necklace named “Carrie” everywhere.

Emotionally attached, Sarah Jessica Parker wore the “Carrie” necklace for years, like a thread line through the series.

However, it wasn’t just necklaces that people branded names on, but belts, in a trend that took monogramming to the next level.

Made famous by Mariah Carey, the most popular 2000s belts had a large silver buckle with Swarovski crystals if you wanted to channel your inner A-lister.

14. Baggy Jeans in Hip-Hop Style

While skinny jeans are synonymous with the 2000s fashion decade, baggy jeans were the signature style in rap music, worn by hip-hoppers and rappers everywhere.

While you could argue that the American comedian and actor Pete Davidson is working hard to bring back this trend, baggy jeans were the go-to look of the 2000s most famous rappers.

Some of the best looks were sported by Jay Z, Kanye West, and LL Cool J., who styled baggy jeans with oversized jerseys and Air Jordan sneakers.

15. Oversized Hip-Hop Accessories

We can’t talk about 2000s fashion without spotlighting those days’ unique hip-hop accessories.

In the 2000s, fashion started to discover the power of status symbols, and designer brands began battling it out to be featured in the latest Black Eyed Peas or 50 Cent music videos.

As such, flashy hip-hop accessories emerged as gold jewelry, oversized sunglasses, and baseball caps.

Let’s not forget the blinged-out arm candy and oversized watches incrusted with precious stones throughout the face and sides.

16. White Tank Tops

While tank tops were a staple of 2000s womenswear fashion, a similar closet essential appeared in menswear.

After being popular throughout most of the 50s and 60s fashion, the so-called ‘wife beater’ tank top was resented in the 2000s.

The classic white tank top was essential for men’s streetwear, often styled with True Religion jeans and the latest must-have Von Dutch trucker hats.

17. Entrepreneur Turtlenecks

The best years of 2000s fashion also gave us a modern icon – the turtlenecks.

The last part of the 2000s decade became a love affair between rappers and turtlenecks, who loved pairing them with layers of chunky gold necklaces.

Turtlenecks were also paired with coordinating jackets as an easy way to elevate the outfit while still staying casual.

18. Cargo Pants

Avril Lavigne called; she wants her cargo pants back.

Military-inspired cargo pants became synonymous with the rebellious Punk style of the 2000s.

Everyone from Girls Aloud to Gwen Stefani and Christina Aguilera claimed the trend.

The style remained popular until now, but if you want to style it in the 2000s, pair it with a graphic t-shirt, coordinating tank top, or tube top.

19. Handkerchief Tops

2000s fashion was also about showing off your legs and midriff.

However, not everyone had Beyonce’s custom-made designer clothes, so people began improvising.

Using ‘what your mama gave you,’ handkerchiefs became tops, eventually turning into a fashion statement that needed just a pair of low-rise jeans and wedge mules to turn you into the fourth member of Destiny’s Child.

20. Tube Tops

Tube tops were another closet essential in the 2000s, visible everywhere, from the red carpet to the beach.

The versatility of the barely-there style allowed easy pairing with boho-style maxi skirts, cargo pants, and cropped jeans.

21. Bandage Dresses

Few outfits scream ‘2000s fashion’ more than a Herve Leger’s bandage dress – a French fashion house founded in 1985 – as everyone from Kim Kardashian to Lou Doillon wore one in the mid-’00s.

A signature garment of Bimbocore style, the bandage dress was so famous that you would find it on every red carpet, worn by the most recognizable celebrities.

While Hérve Léger may no longer be a powerhouse brand, the classic bandage dress silhouette still reigns supreme.

As one of the most figure-hugging silhouettes of the 2000s, the bandage dress’s sexy silhouette became the number-one choice for celebrities like Kim Kardashian, Kate Winslet, and Victoria Beckham.

22. Pirate-inspired Hemlines

Handkerchief silhouettes are another niche trend that bloomed in the early ’00s fashion.

While I’ve already covered handkerchiefs as a top, it’s worth looking at the trend’s impact on hemlines.

With Pirates of the Caribbean standing as one of the greatest films of the 2000s, people took fashion inspiration from Captain Jack Sparrow and his crew.

23. Painted Jeans

Driven by the 90s fashion trends, denim became the incontestable king of the ’00s fashion.

However, not everyone wanted to step out in neon skinny jeans, so more understated color alternatives, such as painted jeans, started to gain ground.

Painted jeans became one of the most popular (and unforgettable) 00s outfits, whether stars, butterflies, flowers, lines, or squares.

24. Baker Boy Caps

Trucker caps weren’t the only headgear that ruled 2000s fashion.

Styled with a sweeping side fringe, knitted beanie caps became an equally powerful style for autumn and winter.

Popularized by 2000s punk stars and hip-hop celebs like Rihanna, slouchy beanies became a hipster staple.

25. Oversized ‘IT’ Bags

2000s fashion is also at the core of the ‘It’ bags, such as Chloe’s Paddington, at times when the influencer culture started to take hold.

In 2004, Chloe’s creative director, Phoebe Philo, debuted a millennial classic, the heavy, top-handle Paddington bag.

Instantly recognizable for its logo padlock, the back claimed cult status at no time, and every one of the 8,000 pieces created sold out before arriving in stores.

Chloe’s Paddington was on the arm of every A-class celeb, from Nicky Hilton to Michelle Trachtenberg.

Building on the oversized bag trend – that could hold everything but the kitchen sink – Balenciaga’s city bag became another memorable IT bag in the ’00s.

While the Olsen twins may have moved on to Hermes bags, they’re primarily responsible for making the Balenciaga City bag one of the hottest trends of the 2000s.

FAQs

Styling Tips

Reviewing the most popular looks of the 2000s fashion, it becomes evident that people took more risks with their outfits and stylistic choices back then.

The influence of TV shows like Gossip Girl and The Simple Life, showcasing the lifestyle of the upper class, introduced a new world of fashion and dressing styles.

Most of the 2000s outfit ideas have evolved from everyday outfits to become trends that we see nowadays reinvented in capsule collections appealing to Millenials and GenZ shoppers.

Whether you embrace the Olsen twins or Paris Hilton 2000s fashion looks, I hope you discovered a few ideas on how to recreate the most representative looks of the 2000s.

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