Personal Shopping Assistant Blog

Top celebrities with the most questionable style through the years

Britney Spears
Oops…she did it again! This Femme Fatale definitely knows how to Work, but style has never been Her Prerogative. Teenage girls back in 1999 and grown women in 2016 we are not giving up hope that Britney will find a professional stylist, who would finally cross her out the worst dressed lists, which she topped for the last couple of decades. We want to see a Brave New Girl in elegant feminine outfit!


Christina Aguilera
Britney’s BFF in past and her main competitor in present, Christina Aguilera, is also known as the queen of questionable outfits. Her signature style back in rocky nineties was to wear everything shiny singer owns, completing the look with crazy intense makeup. Unfortunately, unlike the curves of celebrity, not much changed in her fashion sense. Well, yes, Christina’s makeup did become a little calmer, but do you really notice that behind the ridiculous outfit decisions?


Paris Hilton
Mistress of everything shiny and glamourous might have been stuck in 2003, since it’s the only explanation we have for her Barbie outfits. Total pink, rhinestones and hoof shoes… The great thing about fashion is that always moves forward, maybe Paris should try too?


Lindsay Lohan
This actress hasn’t really moved on from the “Mean girl” faze either.  Although it may sound like a positive thing to same fans (yes, you, we know how many times you rewatched), just looking over Lindsay’s personal outfits over the last decade proves that she really has a thing for weird cloth. We know life has been tough for you, Lindsay, but keep it up, we only wear pink on Wednesdays.


Nicki Minaj
Is it easier to imagine yourself wearing turquoise wigs, furry neon booties, tutus and  nude bejeweled body suits or Nicki Minaj wearing something ordinary and normal? Don’t be scared to pick first option, we are with you on that one.  After all, she’s the queen of outrageous, dynamic, and fearless fashion. (Or we at CheckonBuy may or may not just be too scared of that woman).