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Street Style Vs Red Carpet: 20 Pics Proving Jessica Simpson Always Looks Good

No matter how much negativity has been thrown her way, Jessica Simpson has continued to be herself, and remain best dressed

There are many women in the history of Hollywood that can be defined by the term blonde bombshell. But we don't know if that term can be better applied to any woman more appropriately than Jessica Simpson.

And while Simpson has had some negativity thrown her way over the years questioning things like her intelligence or how her body looked after giving birth, she has always managed to bounce back stronger than ever.

Now in 2018, Simpson still boasts a social media following of millions and her fashion line has earned more than $1 billion.

Below we chronicle the 20 best fashion choices that Jessica Simpson has ever made in her career. Including 10 outfits that she wore on the street (or beach!) and 10 that were either taken for a professional photo shoot or on the red carpet. Because whether walking around town or planning for her photo to be taken, Simpson seems to always dress to impress!

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20 Street - Looking Casual At Wango Tango (2002) 

There are several different music festivals that go on during the summer that allows music fans the chance to experience several of their favorite bands at once. Back in 2002, Jessica Simpson was considered one of the biggest pop stars in the world which made her a natural invite from KIIS to attend their "Wango Tango" concert.

A silly name, but over the years they have recruited big names such as Kanye West and Bruno Mars. While the above photo was taken as she was just enjoying the atmosphere, it's a great example of her casual but flawless street style.

19 JDD - Showing Off Her Assets At The MTV Awards (2003)

Jessica Simpson knows that she has several assets at her disposal that may help draw men in. Simpson revealed in an interview,

"At school, my b**bs were bigger than all my friends' and I was afraid to show them. Now I feel like they make my outfits look better. They're like an accessory," 

That's an attitude that we are sure many people are going to be able to read and take inspiration from, as at the end of the day, it's just her accepting the body she has been given. We're sure having amazing outfits like this which come with raving reviews definitely help with her confidence.

18 Street - Beautiful In Brown

Jessica Simpson was just walking down the street in Beverly Hills back in September 2015 thinking that it would probably just be any other day. But she may have been glad that she chose that particular outfit because it's gone down as one of the best outfits she has ever taken to the street.

The dress may not be fancy enough to make sense on a red carpet or in a fancy photo shoot, but that definitely doesn't mean it should have been kicked from her closet. It's just too bad celebrities tend to get mocked if they wear the same outfit more than once because we're sure her fans would love to see this one again!

17 JDD - Glittering In Gold In 2004

Jessica Simpson doesn't seem like she would need to do much to help stand out in the crowd. But that doesn't mean people didn't still love seeing her shine in a glittery gold gown for the VH1 "Divas" concert and award show. This particular outfit was worn to the 2004 event which at the time marked the 7th concert.

2004 was a year that had several highlights for Simpson, but the most notable may have been performing at the Super Bowl where Tom Brady knocked off the Carolina Panthers. So if you hate Terrific Tom, perhaps you can also place some of the blame on Simpson.

16 Street - Taking In An Art Exhibit For A Date Night

Jessica Simpson wore the above black dress to Tom Everhart's 'Raw' Exhibition back in 2016. And while it may be as fancy as anything she wore on the red carpet, that's literally just an outfit she thought was appropriate to wear out for a date.

We wouldn't blame you if you find yourself being incredibly jealous of her husband Eric Johnson who accompanied her for the nice night on the town. You definitely may also not be too surprised that at the end of the day, the tabloid magazines were talking a lot more about her outfit than anything being displayed at the exhibit!

15 JDD - In The Classic Daisy Dukes

Jessica Simpson may not be in a dress for this photoshoot, but we probably aren't too far off base to say your jaw definitely dropped at least a little bit when you saw this photo. Good luck trying to remember what you wanted to order for food if you had Simpson as your waitress!

While Simpson looks gorgeous throughout this list, her in daisy dukes is perhaps her most famed look. The popularity behind the look skyrocketed with her role in the Dukes of Hazard movie. While the movie didn't have too many moments that were considered all that memorable, Simpson's wardrobe was at least one part that helped the film stand out.

14 Street - Showing Her Valentine's Day Outfit (And Plans!)

When it comes to celebrating different holidays, you may have certain ones that you love spending with your extended family. But for Valentine's Day, you're probably hoping for a much more intimate night out (followed by a significant portion of time spent back at the house!). Especially if you're like Simpson and Johnson who have children together.

She shared the above photo back in 2016 along with the caption "Happy Valentines Day #thisJohnsonIsGettinIt"

Jessica Simpson has had no shortage of boys willing to take her out on Valentine's Day, but for the foreseeable future, it'll be her husband Eric Johnson that gets to do the honors.

13 JDD - One Of Her Faves

There are many outfits that Jessica Simpson has worn over the years that we are sure she absolutely loved and wishes she could wear again. But when she took to Twitter back in 2017, it was this look in particular from the AMAs in 2004 that she wanted to highlight:

"One of my all-time favorite red carpet looks," tweeted Simpson.

She also added the hashtag #ToBe24Again, signifying that she was pining over how her body looked during her younger years. Though something tells us that even if she wore this outfit again in 2018 that she'd still leave everyone's jaws firmly on the floor.

12 Street - Caught Vacationing In Cabo San Lucas

One of the most popular destinations for celebrities to vacation to is Cabo San Lucas. But just because you are leaving North America, doesn't mean that the paparazzi is going to let these celebrities enjoy their vacation without getting some photographic proof of it.

After all, the paparazzi members need to be able to afford vacations of their own right? While Simpson is probably less than thrilled that they were lurking back on March 30th, 2016, there is no question that the person on hand got an eyeful of Simpson in one of her best swimsuits.

11 JDD - Looking Like A Goddess In A Red Dress

We're pretty sure that when you walk through the gates of heaven, this is basically the kind of thing that you get to see. Angel, goddess, ethereal, those are just some of the words that come to mind when we look at this soft picture of Jessica.

While her red dress is more on the casual side, it's no question that it looks fantastic on her all the same. It fits her form, and paired with the beauty of her golden hair, and the framing of the gold on the actual dress, the whole thing is just astonishing to look at.

10 Street - Blue Dress For Date With Eric

Eric Johnson and Jessica Simpson have been dating since 2010 and in 2014, officially tied the knot. Some couples may slow down with going out on dates once they get married, but that definitely isn't the case for Johnson and Simpson who are often seen out and about enjoying Beverly Hills.

And we suppose when you have the ability to go to the fanciest restaurants in town, as they were allegedly doing on this night, you are probably going to get dressed up. We're sure the meal they ended up eating was fantastic, but if Johnson ended up rushing the meal to get back to the house, nobody would be blaming him.

9 JDD - Talking About People's Reaction To Not Being Fat

Jessica Simpson has battled critics about her weight throughout her entire carer. But with the above photo taken for a magazine, it definitely is hard to imagine anyone would look at that photo and think she looks anything but tremendous.

When talking about how it has affected her, Simpson recalled,

"When I walk through an airport and people go, 'You're not fat! I'm like 'Thanks. That's great. Good to know I'm not fat today! Thank you!'"

You'd hope that she would never have to deal with the opposite and have fans come up to her and tell her she's looking awful on her bad days.

8 Street - Walking The Streets Of Beverly Hills

When Jessica Simpson was once asked what she thought about when she got ready in the morning, she replied,

"I always wonder if what I'm wearing will be something that people would compliment, or want to wear. I don't ever get ready just for myself, ever."

Considering she is still a major star in 2018, we're sure that is still a sentiment that rings true. And when you factor in that some of her best paparazzi shots  are still regularly viewed on the internet, are you really going to blame her for being cautious?

7 JDD - Looking Tremendous In 2007

During the time of this photo, Jessica was entertaining the affections of John Mayer behind closed doors. Who, when talking about their lovemaking, described Simpson with high marks,

“Have you ever been with a girl who made you want to quit the rest of your life?”

Jessica Simpson wouldn't be the only person in Hollywood who has experimented with changing up her hairstyle. The above look was donned in 2007 when Simpson attended the Met Gala.

6 Street - Leaving Her Hotel Door Man Ecstatic

When you look at the above photo it's hard to not immediately be drawn to the doorman standing outside of the hotel that Simpson had just left. He looked like he has a smile on that won't be erased no matter how badly the rest of his day goes. At least unless he finds out he's gotten himself fired for staring at Jessica Simpson.

Though we're sure there aren't too many people who would blame him. Simpson may have a gorgeous house, but her hectic lifestyle means she has definitely had years where she's spent more time traveling than staying in one place.

5 JDD - Perfect In Purple

Simpson spent a large portion of her career being compared to other blonde bombshells, such as Christina Aguilera and Britney Spears. She has revealed,

"...trying to be Britney Spears because that's what sells records and then you realize 'All I have to do is be myself. I should have thought of that a long time ago'." 

This photoshoot may have been from a few years ago, but something tells us you won't mind taking a trip back in time to admire Simpson at perhaps the peak of her career.

4 Street - Arriving At The Airport

Jessica Simpson is definitely familiar with needing to travel around the world for work. And while she's spent hundreds of hours in airports, we don't know if she has ever looked as tremendous as she did when she stepped off a plane back in 2016. Perhaps she got informed when she was landing that there were going to be photographers waiting to take her picture!

With a fun floral top, it also looks like he would definitely have fit right in during the '70s. Perhaps she was taking inspiration from the time she made a brief cameo on That '70s Show as a love interest for Ashton Kutcher!

3 JDD - In A Little Yellow Dress At A Charity Event

There are many outfits in a woman's wardrobe that she may feel she holds near and dear to her heart. Such as making sure you have an amazing little black dress. But if you're Jessica Simpson, perhaps right beside that seductive black dress was this trendy and eye-catching yellow number.

She wore the outfit back in 2014 when attending a charity event that seeks to raise financial support for Stuart House, which helps those who have been sexually abused. The event was flooded with celebrities who we are sure were all more than happy to use their star power to help make a difference in the lives of those who really needed it.

2 Street - Showing Off Her Funny (And Beautiful!) Side

Hello my deer 😜

A post shared by Jessica Simpson (@jessicasimpson) on

There are many different elements of Jessica Simpson that helps explain why she is so popular. I mean hell, her 4 million followers on Instagram need to be sticking around for some reason right?

Those fans were surely glad they were already subscribed when Simpson uploaded one of the best Instagram posts of the year.

Along with looking stunning in her outfit, Simpson captioned the photo "Hello my deer"; indicating the antlers that are in the back!

While we aren't sure if this photo was taken in Simpson's house, she surely has the income to support such a fantastic living space.

1 JDD - At The Mockingjay Premiere

When you are a celebrity you don't need to be involved with the production of a movie to land yourself an invite to the premiere. And if you're looking for a reason to get dressed up, that's as good a reason as any.

But we don't know if anyone expected Jessica Simpson to completely rock the house with the dress that she wore to The Hunger Games: Mockingjay Part 1 premiere and perhaps overshadow even some of the stunners involved in the production like Jennifer Lawrence.

While there are many assets of Simpson's body that she loves to show off, she must have been feeling extremely confident in her legs to be comfortable wearing that dress!

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Street Style Vs Red Carpet: 20 Pics Proving Jessica Simpson Always Looks Good