From Canadian tuxedos to animal accessories: The best of Britney Spears’ fashion through the years

Spears’ memoir ‘The Woman in Me’ will be released on 24 October

Kaleigh Werner
New York
Tuesday 17 October 2023 16:17 BST
Related: Britney Spears announces engagement to Sam Asghari

Britney Spears is and will always be “Mrs Extra! Extra!”

The 41-year-old pop star first scored her status as a lauded artist with hits like “Toxic” and “I’m a Slave 4 U” - each song inciting self-confidence and a cult-like following reciting her lyrics as mantras. While her vocals left a heart-shaped imprint in the minds of many, the same can be said for Spears’ one-of-a-kind, provocative style.

From glitzy jewels and furry overcoats to cropped graphic tees and ultra low-rise denim, the teen pop heroine has never missed a beat when it comes to her fashion. There isn’t much Spears can’t pull off – and not a lot she’s been afraid to try either. Between newsboy caps, fedoras, and even small animals, if her base garments didn’t scream Y2K in the late 90’s or early 2000’s, than her accessories sure did.

It didn’t even matter whether she had her famed NSYNC ex-boyfriend by her side, the “Gimme More” artist still wowed every red carpet, front row, and sidewalk. Spears, the queen of the 2000’s, knows how to experiment with style like no other.

With Halloween right around the corner and the Grammy winner’s memoir, The Woman in Me, being released on 24 October, let’s take a look at the artist’s best of the best fashion, from her renowned music video get-ups to her night out attire.

Pink tube top and knee pads

It would be wrong not to start with one of Spears’ on-stage looks that won her the “Princess of Pop” title. Among the number of outfits to choose from is a statement look that’s burned deep in the memory of many: her 1999 pink latex tube top and matching knee pads, worn while performing at the Universal Amphitheatre in Los Angeles, California.

(Getty Images)

With her blond tresses pulled back in two tight pigtails, her baggy white pants with their massive hot pink patches, and platform white sneakers, Spears spun “skater” style and made it girl-coded.

Denim, denim, and more denim

Depending on who you ask, some will say the “Canadian Tuxedo” movement in fashion was led by Spears. You could always count on the powerhouse singer to splice denim or layer it, transforming the fabric’s inherent casualness into glamour.

For the 28th annual American Music Awards in 2001, Spears donned a strapless gown made entirely of jean material. Not only did she pair it with a dazzling drop-down choker, but she matched with her former partner, Justin Timberlake, on the red carpet - who wore the most literal form of a Canadian tuxedo. Thus, the two crafted one of, if not the top sought-after photograph used to piece together the perfect couple’s costume for Halloween.

Spears’ love for a good denim ensemble didn’t stop there. In 2001, just a couple months after she and Timberlake were applauded for their teamed-textile moment, the “Baby One More Time” creator wore a patchwork jean two-piece to the Teen Choice Awards. She paired a low-cut scoop bralette with a high-waisted layered band jean skirt, adorned with a white button-up that was unbuttoned and tucked in halfway.

(Getty Images)

Elegant white gown and shawl

Any talented artist can change their vocal range from a delicate ballad to a rock anthem, but not all can switch their personal style just as easily. Spears always could. If she wanted to bare her midriff and wear knee-high boots, she did. If she wanted to present a proper persona in a long, lush gown, she did.

For the 42nd annual Grammy Awards, fans saw a side of Spears that remained hidden up until then. In a mod white halter-neck dress, a dainty crystal necklace, and a fur-shawl, Spears switched from being a grungy girl to an angelic goddess.

(Getty Images)

Orange and pink bohemian get-up

The jazzy dresser was back for the 2000 Billboard Music Awards, where Spears once again proved capable to make any style her own. In a long sleeve, low-cut flimsy orange and pink tie-dye dress, with a matching print velvet bra and mini shorts over sheer pink tights, the fashionista flashed boho-chic for the cameras.

Spears paired the outfit with a multi-layered colourful choker, a feathered fedora, and pointed-toe red boots.

(Getty Images)

Fur coat and wide-leg denim

To watch a star with your name get inducted into the Hollywood Walk of Fame is a coveted occasion that many celebrities and entertainers never forget. When Spears received hers, the pop sensation was only 21 years old.

In classic Spears fashion, she honoured the moment by dressing like her most authentic self. Spears wore wide-leg denim cargo pants, a pink fur coat, and a ruched embroidered top with strappy silver sandals.

(Getty Images)

Juicy Couture Tracksuit

Spears’ street style was no less emblematic of her creativity than her red carpet looks. Aside from her passion for oversised sweaters and lace-up boots, she struck many with her famed velour tracksuit. Plus, a queen of the 2000’s couldn’t be named queen if she didn’t wear at least one Juicy Couture ensemble. In this case, Spears paired a baby blue tracksuit with a bowling ball bag, white trainers, and tinted wraparound sunglasses.

Music video Britney and 2001 MTV VMAs

Lasly, Spears’ outfits for her “Baby One More Time” and “I’m a Slave 4 U” music videos were revolutionary. With her braided pig-tailed hair, pom-pom accessories, gray sweater, white blouse, mini pleated skirt, knee-high socks, and peak-a-boo red bra, Spears reimagined the “sexy schoolgirl” worn by many on Halloween today.

But Spears confirmed she was more than just a schoolgirl when she performed “I’m a Slave 4 U” at the 2001 MTV Video Music Awards, when she wore a green wrap bra top, mini bedazzled booty shorts, pasted colourful gems all over her body. Not to mention, she donned a thick snake around her shoulders as if it were a scarf.

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