Britney Spears’ Fashion and Footwear Evolution: Her Boldest Style Moments Through the Years

Britney Spears has captivated the world not only with her music but also with her evolving sense of style.

From her early-2000s pop princess days to red carpet glamour, her fashion and footwear choices have reflected the different eras of her career.

Then and now: Britney Spears at the 1999 American Music Awards (left) and striking a high-fashion pose on the Spring 2016 cover of V Magazine #100 (right), showcasing her evolving style and public image (Credit: Judy Eddy / WENN / Chris Connor / Manny Hernandez / Avalon)

Britney Spears’ Style Evolution: Fashion, Footwear, and Changing Beauty Standards

Over the years, fans have also noted changes in Britney Spears’ appearance, fueling ongoing conversations about how style, beauty routines, and possible cosmetic enhancements have shaped her evolving public image.

Standing at 5ft 4¼ (163.2 cm) and wearing a US shoe size 7, Britney is relatively petite—yet she’s consistently used bold fashion and sky-high heels to amplify her presence on stage and the red carpet. While speculation continues, one thing is clear: her transformation is as much about reinvention through style as it is about stardom.

Britney Spears steps out in a blush pink halter mini dress and classic black peep-toe heels while holding hands with then-husband Kevin Federline, known for his laid-back streetwear and bold printed shirt (Credit: INFGoff)

Over the years, some experts have observed changes in Britney Spears’ facial features, suggesting the possibility of cosmetic enhancements.

Britney Spears in her breakout role from the 1999 “…Baby One More Time” music video, wearing the now-iconic schoolgirl-inspired outfit that launched her pop superstardom and influenced Y2K fashion

Britney Spears has openly discussed using facial fillers but has not confirmed other cosmetic procedures.

Over the years, fans have speculated about possible breast augmentation, particularly as her appearance has changed alongside weight fluctuations, motherhood, and aging.

Britney Spears at the 2000 American Music Awards (left) and nearly two decades later at the 2019 Beauty Awards in Los Angeles (right), reflecting her evolving look and public presence over the years

Some media outlets have reported that Britney Spears may have undergone cosmetic procedures as a teen, though she has never confirmed this publicly.

One article from Rolling Stone claimed that her mother approved of breast augmentation during her adolescence, but this has never been officially verified.

Britney Spears claps enthusiastically while visiting her charitable summer camp for kids in 2010

In a 2013 InStyle interview, Britney Spears openly shared her love of skincare and admitted to having lip injections.

Britney Spears at the Los Angeles premiere of Once Upon a Time in Hollywood on July 22, 2019, turning heads in a bold red cutout dress and diamond choker at the TCL Chinese Theatre

Britney’s honesty about her skincare and beauty habits reflects her interest in personal care. Still, her bold fashion choices and signature footwear have consistently defined her public image. Let’s look at how her wardrobe has evolved throughout the years.

Fashion Miss or Statement? Britney’s Bold Sheer Look at the 2017 Pre-Grammy Party

In February 2017, Britney Spears turned heads in a daring sheer embellished dress at Clive Davis’ Pre-Grammy Party at The Beverly Hilton in Los Angeles—an outfit that sparked mixed reactions from fashion critics and fans alike.

Britney Spears wears a daring sheer embellished gown by Brazilian designer Uel Camilo at Clive Davis’ 2017 Pre-Grammy Gala, making a bold red carpet statement

The then-35-year-old pop legend flaunted ample cleavage in a custom dress from Uel Camilo featuring strategically placed bead embellishments.

Britney Spears in a custom dress from Uel Camilo at Clive Davis’ Pre-Grammy Party held at The Beverly Hilton in Los Angeles on February 11, 2017 (Credit: Adriana M. Barraza / WENN)

She styled the daring long-sleeved dress with a deep scarlet eye shadow and sky-high ankle-strap sandals.

Britney Spears pairs her sheer Uel Camilo mini dress with nude ankle-strap heels that elongate her legs and add a sleek finish to her bold red carpet look

How do you like Britney’s attention-grabbing sheer mini dress? Perhaps she should consider hiring a new stylist?

Britney Spears shows off her feet in nude ankle-strap sandals with a bold blue sole, adding a subtle pop of color to her red carpet look while elongating her legs

Billboard Wardrobe Change: Britney’s “Modest” Look at the 2016 Billboard Music Awards

Like many celebs, Britney Spears switches between multiple outfits at the same event. At the 2016 Billboard Music Awards, Brit changed into an outfit that, by the pop star’s standards, was considered “modest.”

Britney Spears receives The Billboard Millennium Award, which was established in 2011 to recognize music singers and their contributions

It’s not the type of outfit we’d think of when we hear the word “modest,” but it was the one that gave her the most coverage throughout the night.

After arriving and performing her greatest hits in skimpy outfits (and showing she had recovered leaps and bounds from her 2007 breakdown), Britney changed into one more press room outfit after being honored with the “Millennium Award.”

Britney Spears flaunts her legs at the 2016 Billboard Music Awards Press Room at T-Mobile Arena in Las Vegas on May 22, 2016

Britney swapped into a dazzling, fully embellished crop top and skirt set by Charbel Zoe Couture, featuring intricate detailing and strategic cutouts highlighting her toned physique.

Britney Spears flaunts her butterfly and vine foot tattoo in silver Stuart Weitzman “Nudistplatform” sandals, featuring metallic ankle straps and bold platforms

The two-piece couture look featured intricate construction and well-placed cutouts to highlight Britney’s toned figure.

However, the ensemble drew mixed reactions, with some critics noting that the revealing design leaned more provocative than polished, especially given its frequent exposure of undergarments.

She completed the outfit with silver Stuart Weitzman “Nudistplatform” sandals, which added height and a sleek, modern finish to the otherwise daring look.

Britney Spears sticks out her tongue as she makes her way up the 2016 Billboard Music Awards press room stage with her Millennium Award

Britney received the “Millennium Award” for her undeniable influence on the industry, and the pop star gave the love back by posting a shout-out on Instagram to her fans.

Stepping Out in Style: Celebrities Who Love Stuart Weitzman Heels

Stuart Weitzman heels have long been a staple in the wardrobes of many celebrities, gracing red carpets and high-profile events with their elegant designs. Here are some notable instances where stars have stepped out in style wearing Stuart Weitzman:

America Ferrera at the 96th Annual Academy Awards

• Event: 96th Annual Academy Awards
• Outfit: America Ferrera dazzled in a pink chainmail dress by Versace.
• Footwear: She complemented her ensemble with custom pink Stuart Weitzman Discoplatform sandals, adding a touch of glamour to her look.

Taylor Swift at the 2024 MTV Video Music Awards

• Event: 2024 MTV Video Music Awards
• Outfit: Taylor Swift made a bold statement in a yellow plaid Dior ensemble.
• Footwear: She paired her outfit with black Stuart Weitzman Ultrastuart Maverick over-the-knee boots, enhancing her edgy aesthetic.

Reese Witherspoon’s Chic Day Out in Los Angeles

• Event: Casual outing in Los Angeles
• Outfit: Reese Witherspoon showcased a chic denim ensemble.
• Footwear: She opted for Stuart Weitzman’s Nearlynude sandals, exemplifying effortless style.

Angelina Jolie at the ‘By the Sea’ Screening

• Event: ‘By the Sea’ Screening in New York
• Outfit: Angelina Jolie looked elegant in a blue Luisa Beccaria chiffon dress.
• Footwear: She completed her ensemble with nude Stuart Weitzman pumps, adding a classic touch to her appearance.

Kim Kardashian in Stuart Weitzman’s Fall 2022 Campaign

• Event: Stuart Weitzman’s Fall 2022 Campaign
• Outfit: Kim Kardashian showcased various stylish ensembles.
• Footwear: As the brand’s ambassador, she modeled the latest boot styles, highlighting the brand’s contemporary designs.
• More Details: Kim Kardashian’s Stuart Weitzman campaign

These instances underscore Stuart Weitzman’s enduring appeal among celebrities, offering designs that seamlessly blend elegance with modern trends.

You can grab Britney’s final BBMA look by fishing for a pair of the Stuart Weitzman “Nudistplatform” sandals at Nordstrom and Zappos.

Teen Choice 2015: Rainbow Hair & Le Silla Sandals

In April 2015, Britney Spears squeezed her body into a tiny dress before posing with her surfboard in the press room at the 2015 Teen Choice Awards at the Galen Center in Los Angeles.

Britney Spears debuted her rainbow hair for the first time at a public event (Credit: WENN)

She debuted her rainbow hair for the first time at a public event while accepting the Candies Style Icon Award.

“Fashion has always been something I’ve loved to experiment with. It gives us all a chance to express ourselves and our own personalities and to shine in our own way,” she said during her speech.

“To all the teens out there watching, be fearless in your choices and don’t be afraid to be yourself.”

Britney Spears in a sparkling silver embroidered dress from the Mikael D Pre-Fall 2015 collection (Credit: WENN)

The then-33-year-old entertainer dressed in a sparkling silver embroidered dress from the Mikael D Pre-Fall 2015 collection.

Rumored to have undergone plastic surgery, she styled the tacky high-low hem dress with Jennifer Meyer jewelry and shiny silver sandals from Le Silla.

Britney Spears styled the tacky high-low hem dress with Jennifer Meyer jewelry (Credit: WENN / Brian To / FayesVision)

Britney Spears, Maddie Briann Aldridge, Sean Preston Federline, Jayden James Federline, and Bryan Spears in the press room at the 2015 Teen Choice Awards held at the Galen Center in Los Angeles on August 16, 2015 (Credit: WENN)

Promoting ‘Glory’ in Style: Aquazzura Boots & Saint Laurent

In September 2016, Britney was making the promotional rounds for her ninth studio album, Glory, released on August 26, 2016, through RCA Records.

Britney Spears in a black coat outside BBC Radio 1 in London on September 28, 2016 (Credit: Tony Oudot / WENN)

It was the pop sensation’s first full promotion on radio and television since her unfortunate downward spiral some years earlier.

Britney was spotted arriving at BBC Radio 1, causing chaos among the fans waiting outside.

Britney Spears arrives for a radio guesting in Aquazzura’s ‘Giselle’ thigh-high boots (Credit: Tony Oudot / WENN)

Britney wore a Saint Laurent pussy-bow floral-print crepe dress underneath a black midi trench coat. The pop completed the look with sunglasses, a black hat, and black suede Aquazzura ‘Giselle’ thigh boots.

Britney Spears arrives outside the radio station in a Saint Laurent pussy-bow floral-print crepe dress (Credit: Tony Oudot / WENN)

Britney guested at Scott Mills’ radio station, where she cheerfully chatted up a storm with the hosts.

The mother-of-two revealed why she hesitated to do a back walkover at the Apple Music Festival, shared a prank video starring her sons, and reminisced about her iconic “Slave 4 U” VMA performance. While Britney’s exact “Giselle” boots are now sold out, you can browse the latest styles from Aquazzura at Farfetch.