Britney turns 40: the looks that marked a whole generation

Britney Spears turns 40 this Thursday, December 2. A very special celebration for the pop princess, since it is the first birthday that she will celebrate in freedom after 13 years of guardianship and the first as the fiancée of Sam Asghari, her partner since 2016.

In her more than twenty years of experience in the music industry, the artist has not only conquered the public with her songs, but also with her looks that have marked a whole generation that has faithfully followed in her footsteps. These are the outfits that made Britney a style icon in the late 90s and early 2000s.

Her first success

The singer revolutionized the music industry with her catchy ‘Baby one more time’. On October 23, 1998, a very young Britney – she was only 17 years old – debuted dressed as a schoolgirl, a look that for years has inspired thousands of fans to dress up for Halloween. In the video clip, which accumulates almost 670 million views, the Louisiana singer appeared with a white shirt tied at the waist that revealed her bra, a black plaid mini skirt and a gray cardigan. A teenage style that was completed with a pair of braids with pink pompoms.

The queen of cropped tops

On her first tour, the artist already made it clear that one of her favorite pieces was the ‘cropped tops’. One of the most remembered ‘outfits’ is this set consisting of a metallic pink ‘bandeau’ top and white pants. In those months she still kept her childish image with her hairstyle with a pair of pigtails.

Pure elegance

Britney debuted at the Grammy Awards in February 2000. Before taking the stage to perform a medley of ‘From de bottom of my broken heart’ and ‘Baby one more time’, the singer caused a sensation on the red carpet with a beautiful white dress with a ‘v’ neckline and straps cutouts that was combined with a matching furry shawl and a striking necklace.

The most imitated monkey

A month later, Britney unleashed the madness again with the first single from her second album ‘Oops!… I did it again’. To set the story on Mars in the video clip, the artist was clear that she wanted a red suit. So she hired Michael Bush, costume designer for several memorable Michael Jackson outfits, who created the iconic red latex jumpsuit that Spears wore with black sneakers that belonged to her.

The queen of extravagance

In December of that same year, the pop princess appeared on the red carpet at the Billboard Awards with an eccentric style in orange and pink tones that captured all eyes. The young woman was presented with a coat-dress with a ‘tie dye’ print that revealed her bra and some microshorts. A set that completed with a hat with feathers. Years later Britney herself admitted to the magazine ‘Harper’s Bazaar’ that her most unfortunate look had been this. “I actually thought I looked gorgeous,” he confessed.

The most complicated jeans

Spears used to combine cropped tops and shirts with low-rise jeans which became one of the most controversial trends of the time. The singer was a great follower of these jeans that she had in different styles, from flared pants to others with rips at the knee.

Matching with your partner

In January 2001, Britney and Justin Timberlake, America’s sweethearts, posed together on the red carpet at the American Music Awards in highly commented denim looks. An image that went down in fashion history and is still remembered today by thousands of followers of the couple. The singer revealed a few years ago that initially it was Britney who was only going to wear her dress made with patches of different denim tones, but when he found out what his girlfriend’s look was like, he decided to go with her. “When you are young and in love you do a lot of things like that,” he admitted.

His most sensual look

A few weeks later, Spears starred in one of the most legendary performances at the MTV Video Music Awards. The artist, who had already presented her third studio album under the name ‘Britney’, showed her most sensual side with the song ‘I’m a slave 4 U’. On stage the young woman wore a suggestive outfit consisting of a green cropped top with rhinestone details and a microshort with the same decorative elements in other shades. He finished off his look with a royal python on his shoulders.

The most criticized design

On the red carpet at the same awards, the singer wore a black lace Dolce & Gabbana dress that was widely criticized because it revealed her black lingerie set. Criticisms that would be impossible today.

The most revealing t-shirt

In April 2022 Britney and Justin Timberlake broke their relationship due to an alleged infidelity on the part of the singer. His ex-partner took advantage of the rumors to launch his solo musical career with the album ‘Justified’, with the odd song dedicated to Spears. Months later, in October, the artist was seen in London with a T-shirt with the message ‘Dump Him’ (Leave him), which many interpreted as a hint to her ex, who had revealed the intimacies of Spears in several interviews.

His failed comeback

2007 was undoubtedly Britney’s worst year. In February he entered a rehabilitation center and a day later the shocking scene of the singer shaving her head occurred. In September of the same year, and after a few months in treatment, Spears reappeared on stage at the MTV Video Music Awards with a lost gaze and unable to follow the choreography. His look to interpret ‘Gimme more’ from his album ‘Blackout’, one of his best works according to critics, did not leave him indifferent: a sequined bikini, boots -with a broken heel included- and badly placed extensions.

His big change

A year later the artist, who had released her sixth album ‘Circus’, reappeared through the front door with a renewed and healthy image. The singer changed her disheveled outfits for more cared looks and with the circus aesthetic as the protagonist.

The most sophisticated Britney

With the passage of time and with her career again at the top, Britney was seen more at events such as Elton John’s annual party in 2013, where she attended with a beautiful long dress full of black sequins and with a suggestive neckline in ” v ‘. During this time, Sean Preston and Jayden’s mother ditched her signature blonde hair for a flattering dark brown hue.

His new uniform

For her residency in Las Vegas, which began at the end of 2013 and lasted until 2018, the ‘Overprotected’ interpreter modified her uniform on stage. Britney replaced the ‘cropped tops’ and pants sets with bodysuits and jumpsuits full of sequins and rhinestones. One of his most memorable designs is the ‘naked’ jumpsuit that was inevitably reminiscent of the piece he wore in the ‘Toxic’ video clip.

The new ‘LBD’

One of the most sophisticated designs that Britney has worn in recent years was Julien Macdonald’s black dress with which she showed her most mature image. The artist triumphed with her version of the ‘Little Black Dress’ with an opening at the neckline, one of the trends this season, and an asymmetric skirt.

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