Worst Celebrity Outfits From The Millennium Decade


Usually when we think of celebrity clothing, we think of amazing designers and awesome duds.  But, some celebs just can’t manage to put together a decent outfit, no matter how expensive the pieces.  It’s strange, disappointing and somewhat thrilling to see your favorite celebrities wear some very strange outfits.  The era of the millennium was even crazier.  Midriffs were everywhere, slip dresses and bra tops abounded.  Here are the best of the worst celebrity outfits from the millennium decade.

1. Jennifer Lopez was a true 00’s girl

From the hat, to the big hoops, gold chain and the velour track suit, everything about this outfit is screaming 2003.  It’s making us strangely nostalgic…


2. Cher was a stand-out

We love this– everyone else is in a tuxedo or how and here’s Cher, wearing sparkly pants and heels, with a matching top and a denim jacket.  Her signature over-the-top makeup is a total plus here.  We love you, Cher.


3. Britney and Justin’s denim disaster

We don’t know whether to be in awe or disgust over this matching ensemble. Denim hit its peak in the early 00’s.  This couple and their matching outfit was a dream come true for so many fans.


4. Alicia Keys fringe bra

After Janet Jackson’s debacle with a ‘wardrobe malfunction,’ this fringe-covered bra that looks like it’s about to burst makes us all a little bit nervous.


5. Hey girl– we can see your bra

J-Lo’s see-through dress is just…not cool.  It’s not a flattering fit and her bra is clearly seen right through the gauzy fabric.


6. Pink looks edgy

Combat boots and an edgy dress is not a typical outfit you see on the red carpet– but Pink likes to do things her own way.


7. And then there’s this little number

This was Pink back in her glory days of being the edgy-cool girl.  This outfit though…just wow.  The hot pink spikes, the fur robe, the tattered jeans and metallic crop top with plastic wedges…it’s all just a bit too much.


8. Paris and Nicole’s denim dreams

Last time I checked, I didn’t think it was ok to wear a jean jacket sans bra and shirt…but hey, I’m no multi-million dollar celebrity.  We’re digging the chokers, low-slung jeans, hair twists, and exaggerated eye makeup that completes this look.


9. Rihanna before she turned into bad girl Ri-ri

Rihanna hasn’t always been terribly edgy.  She used to wear outfits that matched– like this pink and white halter top with matching underwear and shoes.


10. Kim K’s trashy slip dress

This was back before Kim Kardashian was full-on famous.  She was probably working as Paris Hilton’s assistant.  The 00’s was also a decade when negligee’s became mainstream and it was ok to wear lingerie-like clothing in public.


11. Nicole and Nicky’s silk dresses

Because of the uptick in lingerie-like clothing that was worn by celebs, silk was a popular fabric.  Which is unfortunate, because silk shoes armpit stains, sweat and grease.  Not that we see any of that on Nicky or Nicole…


12. J-Lo’s plunging neckline

Apparently, Jennifer Lopez likes to show off her mid-section and wear clothing sheer enough to see her underwear.


13. Paris Hilton’s braids-n-bra

Paris complemented her low-slung jeans with a wrap-around bra top since showing off your toned tummy was the coolest thing to do during the 2000’s.  Her fake braids add another level of coolness.


14. Christina’s signature look in the 2000’s

X-stina wear two hats, a red-eye color, black and white hair extensions, a halter bra-top and a very mini skirt. We hope this is one of those outfits she looks back on and says “what was I thinking?”


15. Alicia Keys overtaking sweater

We hope it was a really cold day on the red carpet to make Alicia wear this giant sweater-poncho complete with a hood.