Oops!…Let’s Do it Again? Britney Spears Outfit Ideas

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Britney spears with justin timberlake

Last Updated on June 21, 2020

Let’s dive all the way back into the 90s to the looks of the Princess of Pop: Britney Spears. She is the best-selling teen musician ever, so, it comes as no surprise that her fashion style was an equal hit.

Britney ́s stage life started early, she went to New York City and at the age of eight enrolled the Professional Performing Arts School. Since then she escalated to the top but it was the ninth decade of the late twentieth century that saw her bloom.

Her outfits and the trends that followed were highly covered by the media, reflecting the immense success only comparable to Michael Jackson, king of the same music genre. In case you don’t know, this lady has six Guinness World Records!

Read on and get ready to revisit her memorable evolution throughout the nineties. Fear not, you won’t have to crop all your clothes, wear low rise jeans or squeeze into bandage dresses.

Below are Brit´s best beauty choices and matching statement moments to love, recall, and repeat!

One more time

The iconic outfit that will look good any day of the week. You know what I’m talking about, the garb in “Baby One More Time” music video.

This was set in a high school environment, where Britney sings and dances away in a tweaked catholic uniform. Your street version of it: take a button down shirt and pair it with one of your skirts, favour the short over the long ones, if it gets chilly top it with a cardigan and you’re good to go!

If you want to see casual variations worn by other celebrities, look up photos of Avril Lavigne while launching her 2008 album, or Ariana Grande in 2018, during a show in Tokyo.

You can also try it in monotone — US Open throwback moment — simply match tops and bottoms and march in (perhaps in yellow) just like Brit did.

Britney Spears – US Open – Arthur Ashe Kids Day Show (1999)

When you want to go “Crazy”

Spears festive lifestyle is highlighted with a bit — or should I say, a whole lot — of bling. From simmering hats, beaded bras with matching shorts and trousers (like the 2000 MTV Video Music Awards ensemble),

bejewelled one shoulder dresses, to the “Toxic” sheer and sparkling bodysuit, I believe she managed to cover all possible events, pieces, and accessories, inc make-up, in some serious spark. Accordingly, for your Christmas party or New Year’s Eve, there are multiple options to ensure you comply with the annual gleamy dress-code.

First things first, 1999 “You Drive Me Crazy” outfit, easily replicated with a satiny top and flared black jeans or pants or you could even get away with leggings! Also one doable as a single colour option as Britney did that same year, for the Grammys.

If you want to switch things around, try the shine on the bottoms as she did for the Teen Choice Awards or with the patent-leather pants in Los Angeles. And speaking of patent-leather, there are two outfits worth mentioning, the “Oops, I Did It Again” red jumpsuit and the yellow suit she wore at Jay Leno.

Red Jumpsuit

Last piece of advice: Pink is always a good idea and pigtails can make the whole thing even more, Britney, and very photo-appropriate!