Celeb outfits from 1999 will make you smile and cry at the same time

There really is nothing better than looking back at old pictures of celebrities in VERY cringe-worthy outfits (we won't mention our own mistakes).

From tiny bags, to sequin crop tops; sit back, relax and enjoy these 1999 flashbacks:

Britney Spears

Britney's sequin snakeskin flared trousers were perfectly on trend back then. We won't even mention the bronze cropped jacket though.

 

Christina Aguilera

Christina's outfit was on point with her maxi skirt and glitter slogan tee.

 

Destiny's Child

Crop tops were a major deal back in 1999. So were matching outfits.

 

Mandy Moore

Mandy took maxi skirts and tartan to a whole (very pink) new level.

 

Jennifer Love Hewitt

Because showing off some leg was very risqué back then.

 

Sarah Michelle Gellar

All-over orange was a big trend, as were all-over sequins. We can only hope it never comes back in though.

 

Melissa Joan Hart

Melissa clearly love her tiny bag; we're not too sure about the rest though.

 

Jennifer Lopez

Hands up who else had a sleek pair of pedal pushers? Fine, we'll admit to it.

 

Liz Hurley

Forgetting her bright pink leather co-ord for a second – can we just LOOK at her clear perspex heels?!

 

Cameron Diaz

Dresses paired with trousers and kitten heels were so in – NOT. We're sure Ms Diaz is looking back in fashion shame.