11 Hollywood Celebrities With Cringeworthy Fashion Sense

Celebrities With Cringeworthy Fashion Sense

It is completely normal for everyone to assume that all celebrities should have a great dress sense.

After all, we always see them completely glammed up on the red carpet! a lot of them step out wearing very flattering dresses, and their hair and makeup are always just right.

A plus on the sides of celebrities is that they can afford to hire as many stylists and makeup artists as they want to help them look just right for their outings.

However, despite what we would like to assume about celebrities being perfect fashion role models, there are a couple of them who have not always looked so good.

A lot of beautiful women in Hollywood were one time known for their terrible fashion sense, but thanks to an upgrade in the quality of wardrobe managers and makeup artist we have in the world these women have been able to upgrade to an impressive standard.

The fact that for many years the entire world was in shock about the kind of things that these celebrities dared to wear, is the reason I decided to put all of them together in this article.

And also to remind you that even if your dress sense is the worst right now, in a couple of years you can become a fashion icon.

1. Britney Spears

Britney Spears
(Photo by Allen Berezovsky/WireImage)

It is difficult for you to find anyone who has never been a fan of Britney Spears music. However, when it comes to her fashion sense, we dare not to say the same. Britney is one pop star who has never been revered for her questionable wardrobe choices.

Instead, she has always managed to find herself on the list of stars with the worst fashion sense. in the early year, 2000 spares were notorious for attacking and trashy outfits.

She always appeared on red carpet events dressed in wrongly matched outfits they made it seem like it took her five minutes to think of what to wear.

Britney Spears gravitated towards revealing tops with mini skirts that looked sloppy and barely had her body covered.

Brittany also loved to accessorize, and she always went for the tackiest of accessories like chains and Fedoras. it is difficult to forget that one time when Britney Spears wore an all-denim dress to an MTV movie awards; that was the weirdest look ever.

Whenever Britney Spears even attempted to go casual, she usually would opt for mercy old t-shirts and oversized sweaters that only look too good to be worn as a sleep attire.

Today we can say all of that was in the past as it appears that Britney Spears has taken her time to invest in refining her style and that investment is yielding good returns.

2. Helena Bonham Carter

Helena Bonham Carter

The entire world fell in love with Helena Carter in movies like Sweeney Todd and fight club. but if there is one thing we do not fall in love with that would be this eccentric actresses sense of style.

It is true that on the big screen she’s all dolled up and looking glam but what about when she’s off duty?

Paparazzi shots usually show this actress looking sloppy and dishevelled. qatar is no stranger when it comes to mixing mismatched prince and pieces that don’t go together at all.

From her terrible fashion pictures, we can tell that she’s one person who loves to put on comfortable clothes that explains why she goes for oversized items.

However, her love for comfort often makes you appear shapeless against her petite frame. even when Helena has to make red carpet appearances, she’s usually in favour of dresses with a bulk of materials which usually end up making her look like a pin in an ocean.

This actress has taken his few steps back in recent years to focus on her family, but one thing we are not sure of is whether she has decided to upgrade when it comes to fashion or remain where she was years ago.

3. Beyoncé


Before you snap my neck off, I agree that Beyonce is queen and right now she’s everything fashionista. but can we say the same for her days as a member of destiny’s child?

Before Beyonce went solo, it appears that she never knew what would fit her right. the singer rocked quite some questionable outfits on the red carpet at the time.

Beyonce seems to always be in favour of shiny clothes and jewellery the blings and excessively decorated dresses made her look very immature.

We agreed that everyone still loves her at that time because she made good music and her still just good music but her dresses made it seem like she was trying too hard to impress.

Today Beyonce is everything glamorous and sophisticated as a matter of fact the queen and mother of three is everything to look up to when it comes to fashion.

4. Christina Aguilera

Christina Aguilera

Christina Aguilera is one Hollywood star who has made some of the biggest fashion mistakes as far as Hollywood is concerned.

Aguilera know that has a good personality and a very controversial career, but the singer has aggravated towards very trashy and raunchy outfits in the past. if you were a fan of Christina in early 2000, you would agree with me that that period was the prime of her poor fashion choices.

The singer usually showed up at events dressed in scantily-clad outfits that did only hug her in the wrong place.

Aguilera like to trial trends that only a daring person would try out and she also made efforts to show as much skin as possible. something else she did not hesitate to mess up was her hair and makeup; she always makes sure they were outrageous as her costumes were.

But like they say nothing lasts forever and that includes a terrible fashion sense since Christina Aguilera became a judge on the voice she has done everything possible to make sure that she upgrades her sense of style.

No doubt every once in a while she makes some tiny fashion mistakes, but we can say that her style now looks more refined and grown up.

5. Nicole Richie

Nicole Richie

It’s amazing how Nicole Richie and the dove becoming a successful fashion designer considering she had made some of the worst fashion choices in the past.

During the cold days on the simple life or she did was rock the world with her questionable fashion choices without any sense of guilt.

It appears Paris Hilton wasn’t much of a good influence on her. If my memory serves me correctly, Nicole Richie usually would appear on red carpet events putting on tube tops and super short mini skirts.

Richie would probably put on a completely pink outfit or go for something that matches what her best friend Paris Hilton was wearing.

There were times she went for oversized clothing that did nothing at all to compliment her petite frame. All of these make it difficult for me to understand how she went from being confused fashion wise to becoming successful in the fashion industry. this can be nothing short of a miracle!

6. Gwen Stefani

Gwen Stefani

Gwen Stefani was so much of a fashion failure that each time I saw her on television I had to close my eyes. Yes she has turned everything around by becoming a successful fashion designer. Everything and Stephanie wore from the 90s to early 2000s was nothing short of a huge joke.

The singer would show up on red carpet events dressed in foreign bikini tops with very funny skits and platform flip flops. She was the chief icon when it came to revealing and trashy clothing.

Something else going tried hard to put out there was her love for weird and bizarre hair and makeup. right now we love Gwen Stephanie so much not only for her songs but also for the improvements you have made fashion-wise. Gwen, we are super proud of you, and we hope that you only keep getting better.

7. Paris Hilton

Paris Hilton
(Photo by Tibrina Hobson/WireImage)

Paris Hilton was one of the most confused people in the early 2000s. this blonde socialite, all of a sudden, became synonymous with sparkling tiaras wearing all pink and also trying out girly miniskirts. Paris loved putting on juicy couture tracksuits and even make sure that she on them in different colours.

Even though she was nothing close to a fashionista a lot of girls still are fashion inspiration from her terrible fashion ideas probably because she was on the pink side of life. today, Paris Hilton has repented of her fashion sins and can now dress like a very normal person.

She has not found a seat on the front row when it comes to becoming a top-ranking person in fashion, but she has done well for herself, and one thing she still hasn’t let go of is her tiny chihuahua.

8. Jessica Simpson

Jessica Simpson

I really don’t understand what it is with Jessica Simpson; she seems to find herself on every bad list.

If she isn’t listed as one of the Hollywood stars with the worst personal hygiene, she would be listed as one of those with the worst fashion sense.

While this actress is absolutely gorgeous, it appears that for a long time she had no idea how to dress. Jessica gave us the feeling that she was always trying to look hard hot and that wasn’t even necessary because she was naturally beautiful and hot.

On the red carpet, Jessica Simpson preferred to put on things like a corset on very tight dresses that looked completely uncomfortable.

We are glad that Jessica has been touched by an angel and she’s currently finding her footing in the world of fashion. The actresses style has improved vastly and she currently works as a fashion designer.

The mother of two dresses really good for events now. and even though she has received some very harsh criticisms for her maternity fashion style, we think that she has done a great job so far fashion-wise.

9. Katy Perry

Katy Perry

You do not need a suitor to tell you that Katy Perry has a wild sense of style. and even though we still have a reason or two to complain about the things she wears these days, it can never be as bad as when she first showed up on the musical scene.

When Katy Perry was just beginning to get famous, she did not seem to know what was right or wrong to wear.

She was usually associated with things like ridiculous headpieces and the most terrible makeup you can ever imagine and all of that added up to make her on the biggest fashion failures. Her dresses these days has become more tolerable, but she still opts for bright colours and patterns which can be considered daring.

We are so happy for this California girl because she has been able to find her style and we are impressed with the choices she has made recently. We look forward to seeing more awesome dresses on the red carpet.

10. Snooki


When jersey shore was at its peak, Snooki was considered a reality TV princess. Snooki became very famous for how weird and crazy antics on the reality TV show but she was equally very famous for her terrible sense of style.

Snooki had a thing for putting on neon colours and ratchet outfits. Snooki loved to wear crop tops with slogans leopard print tight fitting dresses and some bum shorts.

One other annoying thing that Nokia could not just keep away from her wardrobe was her collection of enormous ugly boots.

Where allowed to scream hallelujah right now because Snooki has upgraded her fashion sense since her time on the show. Her fashion sense can still be considered trashy, but it is everything better than what was.

11. Jennifer Lopez

Jennifer Lopez

Jennifer Lopez is an absolutely awesome woman, so we need to find another word to describe her dress sense instead of a poor sense of style. Right now JLo is known to be very sophisticated when it comes to fashion, but in the early 2000s, her fashion was cringeworthy.

Jennifer’s fashion style back then was a pair of baggy pants with crop tops even on the red carpet she wore things that would make you drop dead and topped them up with cowboy hats.

Now Jennifer Lopez is everything awesome when it comes to dressing up for the red carpet, and a lot of young stars now see her as a fashion role model. (Did you know, Google Image search started because of JLO)

Lots of Hollywood celebrities should be on this list. However, we decided to put together only these 11. If you feel there are other celebrities that you would love to add to this list, please feel free to leave a comment below.

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