Celeb Goss Fashion

31 Britney Spears Fashion Moments We’re Still Obsessed With

08 January 2020

Sure, it’s the start of a new decade, but you’d forgive us for being stuck in 1999 when it comes to Britney Spears. She’s arguably one of the most iconic performers of our time and the same can be said for her wardrobe. Since the late ’90s, Britney has been sparking wardrobe envy in all of us, especially if her outfits could give us the same dance skills. So while you’re making your 2020 fashion resolutions, don’t forget to add ‘be more like Britney’ to your list. After a round-up of Britney Spears’ most iconic fashion moments? Look no further!

Baby One More Time music video, 1998

Don’t lie, you knew every step to this iconic dance routine. TBH, I still do. However, what really stole our hearts were the absolute fire looks in this video clip. If we had to pick just one, our favourite has to be the pink crop combo. It’s by far the most wearable (people tend to give you weird looks if you show up as school girl Britney at work).

…Baby One More Time Tour, 1999

Here it is again but this time we’re treated to pleather hot pink knee pads and a pleather boob tube. ICONIC.

26th Annual American Music Awards, 1999

Did you see the Golden Globes red carpet this year? It was full to the brim with blush dresses. We’re not surprised to see that Britney did it first.


Let Me Love You Babe Dress In Blush Sequin
Beautiful Day Maxi Dress In Blush Sequin
Miss You So Much Maxi Dress In Blush

MTV Video Music Awards, 1999

We’re all out here catching up on Kim Kardashian’s boob tape hacks but it looks like Britney knew them before Kimmy did.

Teen Choice Awards, 1999

This look screams pop star, and honestly, that’s the energy we’re chasing in 2020.


Don’t Say A Word Two Piece Set In White Denim
The Real Me Two Piece Set In White

Sometimes music video, 1999

We’re also here for off-duty pop star vibes courtesy of this cosy AF look.

Billboard Music Awards, 1999

In 1999 Britney knew lilac would be trending again for Spring/Summer 2019/2020.


Stay In Touch Dress In Lilac
Tonight Is Ours Skirt In Lilac Floral Satin

Oops I Did It Again promotional tour, 2000

We’ll never stop extolling the virtues of wrap dresses, wrap tops, wrap skirts, wrap anything really. You can imagine how glad we are Britney is a fan too.

Teen People’s anniversary party, 2000

The cut-outs, the neon snakeskin print, what’s not to love? Also, shout out to that utility belt and its third appearance on this list.

Billboard Music Awards, 2000

Okay, so maybe the execution wasn’t there on this one, but tangerine is having a massive moment and we’ve traced it back to Britney Spears. Plus, tie-dye is having a revolution of its own. Clearly Britney knew what 2020 was about way back in the 2000s.


Love Fuel Dress In Blush Tie Dye
Saw The Light Dress In Tangerine Satin
It’s Cocktail Time Dress In Coral Satin

27th Annual American Music Awards. 2000

Treat this image as visual proof that Britney Spears invented the jumpsuit.

42nd Annual Grammy Awards, 2000

For all the hype LBDs deserve, white dresses tend to get overlooked. This white dress worn by Britney Spears at the Grammys thankfully gives white dresses a moment in the spotlight.


These Tulips Dress In White Sequin
Drop Your Love Knit Dress In White
One For The Money Dress In White

42nd Annual Grammy Awards after-party, 2000

Sequins, beads and chiffon?! There’s no such thing as too many textures.

MTV Video Music Awards, 2000

Only Britney could make us think low-rise anything is a good idea.

The Today Show, 2000

The bold florals and the cowboy boots, no wonder we’re obsessed! We’d happily wear this look to any 2020 festival.


Loves On My Mind Dress In White Floral
Final Resort Two Piece Set In Berry Floral
Therapy – Skylar Boots In Black Smooth

Teen Choice Awards, 2000

I honestly hope this award was for Britney’s work in giving lilac the recognition it deserves.

American Music Awards, 2001

I mean can you have a list of Britney Spear’s iconic fashion moments without including this banger? Britney and JT make a serious case for double denim here. It has to be one of the most recreated red carpet looks of all time.

MTV Video Music Awards, 2001

Excuse me, Tana Mongeau, Britney wants you to know she did it first.

London premiere of Crossroads, 2002

When in doubt, sequins are always a good idea.


Shiny Thing Dress In Silver Sequin
Three Of Us Dress In Silver Sequin

28th Annual American Music Awards, 2002

Little pink dresses, get around them, stat.

43rd Annual Grammy Awards, 2002

This is definitely one of Britney’s more demure looks but she pulls it off just as well. The totally 2000s neckline is one of the things we miss so much about that era.


Commit To Me Maxi Dress In Red
Don’t Catch Feelings Dress In Red

MTV Video Music Awards, 2003

Britney’s newly-single energy post her split with JT is something we all aspire too! Take note ladies, this is how you do breakups.

Oops! I Did It Again music video, 2004

There’s a reason this look trends every year for Halloween. We all want to look as iconic as Britney, even if it’s just for one day.

Billboard Music Awards, 2004

The naked dress has come so far since Britney stepped out on the red carpet in this look in 2004. However, it’d be remiss not to include the OG when thinking about looks we’re all still recreating.

NRJ Music Awards, 2004

What did we say about sequins? When paired with Britney Spears, you really can’t go wrong.


Let The Beat Drop Dress In Gold Sequin
See The Way Slip Dress In Gold Sequin

Backstage at fashion week, 2007

The balletic neckline, the sleek low bun, the fact she’s standing in third position. Britney wants to remind you all she’s a dancer at heart.

MTC Video Music Awards, 2008

One more time for those in the back, Britney rocks sequins like nobody else.

The Circus Starring Britney Spears tour, 2009

Sure, we’re not recreating this look every day. However, you can’t tell me this isn’t one of the first things that come to mind when you think about Britney’s best fashion choices.

Southern Style St Bernard Project event, 2011

We’re living for this neon revival.

MTV Video Music Awards, 2015

I repeat, SEQUINS.

MTV Video Music Awards, 2016

Finally, a very Britney-esque ode to the LBD, courtesy of the most daring neckline we’ve ever seen.

Britney forever by Emma Roffey