We all know about Jessica Simpson, but the truth is her sister is way hotter than she could ever be. Ashlee Simpson is the sister that’s hotter and way more deserving of fame than her sister ever could be. There’s something about Ashlee Simpson that just draws people in. Her beautiful eyes, amazing hair, slender frame, and healthy skin all make it impossible to keep your eyes off her. She’s also younger than her older sister Jessica, meaning she’s got a lot more years left of her youthful good looks.
Like her sister, Ashlee Simpson is huge in the entertainment world. She has acted in television shows and commercials since the age of 15, and she’s also a singer. But she really started to make it big when she was part of various reality television shows. She even made her own reality television show. She has dated quite a few guys over the years, but is now happily married and she’s even a mom. Despite her pregnancy, she looks better than ever, and her amazing hotness shows no sign of slowing down.
With such a long career in the spotlight, Ashlee Simpson definitely has her fair share of hot pictures. Each photoshoot is hotter than the last. It seems inconceivable that someone so hot could stay in her sister’s shadow for so long (she even had a song about it), but after you check out these unbelievable pictures of Ashlee Simpson, you’ll realize that she is by far the hotter sister.
15. Green Socks
When she was young, it was clear that Ashlee Simpson was incredibly hot. She seemed to want to set herself apart from her sister, going with black hair instead of blonde like Jessica. And the look works perfectly for her. I’ve always been of the opinion that black hair is way hotter than any other color of hair, and Ashlee Simpson just proves my point. Blonde hair is so cliche and boring, and I think way too many girls are dying their hair blonde when they should just be sticking with their natural hair color. This photoshoot shows off Ashlee Simpson’s sexy but playful side, and pictures like these definitely got her on a lot of people’s radar. Although it’s sexy, it’s not too sexy, and it’s classy enough not to ruin her reputation. This picture was taken early on in her career, when she was still getting started. However, by this time she was already quite a successful young actress on television and in commercials.
Unlike the previous picture, this picture is just full on hot. She’s going for the sexy schoolgirl look and she pulls it off amazingly. Again, she’s very young and her black hair is ravishing. I love the way she’s playing with her hair in a teasing manner. As your gaze drops down past her face, you’re immediately confronted with the low neckline of her shirt, and the ample amounts of cleavage it reveals. Then, your eyes meet her white knee high socks. To me, this is what makes the outfit. There’s something about socks that is just incredibly sexy, and I think Ashlee knows this all too well. This is a picture that went down long ago as one of Ashlee Simpson’s hottest ever pictures. This wasn’t long after Ashlee Simpson had landed a role on 7th Heaven, an accomplishment that would propel her further into fame.
13. The Rocker
Ashlee Simpson always had somewhat of a hardcore, punk image, especially back in her younger days. I suppose that could have been a rebellion against her older sister’s more classic good looks. Think about it: Jessica Simpson is this classic, all-American blonde that looks like a cheerleader that you’d see in high school. Imagine being her little sister. Wouldn’t you want to do something different? This seems to have been Ashlee Simpson’s rationale, as she went for a much more punk look in her younger days. This is summed up by this picture, where she poses in front of an electric guitar with black clothes on. It’s still a very hot picture, especially with the addition of those amazingly sexy knee high socks that we know she loves so much, but it also conveys a sense of darkness. This image also alludes to Ashlee Simpson’s budding music career, which was just beginning to take off at the time this picture was taken.
If you were going to make a list of the sexiest types of clothing, fishnet stockings would rank pretty high up on that list. In addition, this is also the moment that Ashlee Simpson decided to go back to her natural blonde. And no one can say that it didn’t suit her. She looks sexier, yet also much more mature, like she’s growing up from being a little girl into a fully formed woman. And it wasn’t just her appearance that became more matured. It was also her personality and her professional career that matured. She was devoting more and more time towards her singing career. She had released her debut single “Pieces of Me” in 2004. This single became a huge hit, reaching the top five spot on the US Billboard charts, and enjoyed success internationally as well. The single was part of her debut album, Autobiography, which went triple platinum in the US – just like her hair here!
11. Wild Child
Although Ashlee Simpson was growing up fast, she was still a wild child at heart. This picture really sums up that wild side of her. She’s wearing a totally sexy dress that shows off TONS of cleavage, and she’s sticking out her tongue to the camera in a naughty, cheeky, and undeniably hot way. Her wild style comes as no surprise when you consider her musical influences, like Guns N’ Roses, Gwen Stefani (and No Doubt), Joan Jett and The Runaways, Madonna, Pat Benatar, Green Day, Alanis Morissette, Fiona Apple, Chrissie Hynde, and Debbie Harry from Blondie. All of these bands and artists are pretty hardcore, and their mix of punk, rock, and pop influences no doubt led to her wilder persona, especially when it came to her musical career. When this picture was taken, she was moving out of her “punk” phase, and into a more polished pop singer persona.
10. All Grown Up
Fast forward to a few years ago, and Ashlee Simpson looked like a completely different person. At this time, she started having a lot of relationships with various guys. And judging by her looks, it comes as no surprise that guys were fighting over who got to date her. This picture is just a testament to that. It’s one of the hottest pictures ever taken of her, and shows that just like fine wine, Ashlee Simpson gets better with age. Her hair is both feminine and amazingly stylish, and her eyes and lips look positively alluring. In the past, Ashlee Simpson has had a relationship with Pete Wentz of Fall Out Boy. This relationship got a lot of media attention, but was not made to last, though they had a son together. She also dated actor Josh Henderson, but again, that relationship was not made to last. But little did she know, at the time this picture was taken, she would soon after meet the man of her dreams…
9. Pregnant And Hot
In July 2013, it was reported that Ashlee Simpson started dating actor Evan Ross, son of singer Diana Ross. The two seemed made for each other and they soon announced an extra special message to the world: Ashlee was pregnant! Not long after that, Ashlee Simpson sauntered out into the spotlight with a very large baby bump for all to see. Even though she’s pregnant in this picture, she still looks very hot and sexy. Indeed, maybe it’s because she’s so hot and pregnant that she looks so good! As you may know, pregnant ladies are being bombarded with tons of hormones that are being released in their bodies. Some of these hormones make them moody and crave certain foods… But the other reaction to these hormones is that the pregnant lady can crave something else entirely – sex! You can really see it on Ashlee Simpson’s face that she’s very hot and bothered, and that’s totally sexy.
8. Classy Lady
You may have noticed that there’s something different about Ashlee Simpson when compared to her previous pictures. It’s hard to put your finger on, but something just seems… hotter… more refined… You’d probably never guess unless it was pointed out to you, but Ashlee Simpson actually got a nose job back in 2006. And say what you will about plastic surgery, she definitely looks a lot hotter as a result. It was pretty much the missing link between her and extreme hotness. I personally have no problem with plastic surgery, as long as it creates hot women like Ashlee Simpson! This image really shows off her sexy new face, complete with a sheer black top that show off glimpses of her nude body beneath. Before she looked hot. Now, with her new nose job, she looks like a sexy, classy lady and one of the hottest women on Earth.
Sometimes you don’t have to show too much skin for a hot picture. This picture of Ashlee Simpson just proves that point. She is wearing one of the most fashionable outfits ever, and yet she still looks totally hot and sexy. Her whole look is very “clean” and everything looks immaculate. Her hair remains that sexy, honey blonde tone, and her makeup is done up in a very mature, sexy way with her eye shadow done in a much more tasteful way than she had done in her younger years. The black choker on her neck is both fashionable and artfully sensual. Her dress is scandalously low cut, showing off ample cleavage. This is the cherry on top of the cake. Outfits like these really show off Ashlee Simpson’s ability to look fashionable, sexy, and mature all at the same time. It was around the time this picture was taken that fashion writers started to take note of Ashlee Simpson’s budding and respectable fashion sense.
6. A Healthy Glow
One thing about Ashlee Simpson is that she has really great skin. And unlike a lot of the other stars out there, she doesn’t plaster her face with makeup to hide her blemishes. It looks really natural! Great skin is a sign of incredibly good health, and she certainly looks extremely healthy. In fact, she seems to have an amazing “glow” about her. It’s like she’s radiating some kind of angelic aura that’s easy to see, even from pictures. And this healthy, sexy glow is no doubt even easier to see when you lay eyes on her in person, in the flesh. Another thing about her that’s really evident in this picture is her eyes. She has some of the most beautiful eyes I’ve ever seen. Most of the time, it’s a woman’s eyes that are the selling point for her sex appeal, and Ashlee Simpson is no different. Her eyes radiate a stunning grayish blue, and combined with her healthy glow, make her a very sexy woman indeed.
5. Pure Perfection
Ashlee Simpson is famous for her angelic image. This image is no better summed up than in this picture. Ashlee Simpson really does look like something sent from heaven, although in the form of a hot, sexy woman. But Ashlee Simpson herself was not safe from controversy in her career over the years. Many people hated her for various things, and she was embroiled in controversy from time to time. The number one thing that she caught a lot of flak for was her decision to get a nose job. A lot of people complained that she was not setting a good example for young women, even though her father claimed the nose job was to “fix a breathing problem.” The other main thing she did that was controversial was when she was caught lip syncing on SNL. She then tried to do a dance to cover it up, but she just made herself look worse, something which she knew all too well, and admitted her mistake later.
4. Punk Suspenders
Something that has been present all throughout Ashlee Simpson’s career is her punk-rock look. This look was something she relied on in her earlier career heavily. She was known by music critics as an “anti-Britney Spears” character. That is to say, she was presented as the exact opposite of the famous pop singer. Instead of being blonde, Ashlee Simpson dyed her hair black. Instead of wearing cheerleader outfits and slutty schoolgirl outfits, Ashlee Simpson opted for a more punk look, typically dressing in all black with lots of eyeliner. She was compared to artists like Avril Lavigne and Green Day for these reasons. But later on, after switching back and forth from her natural blonde hair to dyed black, she settled on a more mature look. This is similar to the decision made by her contemporary, Avril Lavigne. But she still retained some of that punk-rocker look that made her so famous earlier in her career. And today, she’s able to mix in punk fashion to her look, appearing sexy, mature, and characterful all at the same time.
3. Dangerous Woman
As previously mentioned, Ashlee Simpson has had quite a successful career in acting in the past. In fact, she initially thought that acting would be her main career, not singing. And with a face and body like hers, it’s easy to see why she was so successful on the big and small screens. Pictures like these really show off what a fine specimen of a woman she is. And these pictures also show how expressive she can be with her face, a key component of being a good actor. She really can look really dramatic and convey a lot of emotion when she wants to. Early on, she appeared in television shows such as Malcolm In The Middle and 7th Heaven, appeared in numerous commercials, and made an appearance in the film The Hot Chick.
2. Yellow Bikini
Throughout her whole life, Ashlee Simpson has lived in the shadow of her older sister. She’s always been trying to break out of that, and tried desperately to get people to notice her. She had to resort to a lot of crazy things in order to change people’s opinion of her. For the longest time, she was known as just, “Jessica Simpson’s little sister.” She wasn’t really famous in her own right. But as the years passed, Ashlee Simpson got more and more adventurous with showing off her body. She posed in bikinis for sexy photoshoots, and the results are stunning. These images are quite old now, but they serve as a reminder of how far she had to go to break out of her sister’s shadow. She even wrote a song about it, called “Shadow,” which was all about how she viewed her older sister’s huge success.
1. Red Bikini
The hottest pictures of Ashlee Simpson are undoubtedly from when she was much younger. It’s pretty obvious why. People are just a lot hotter when they still have their youth. It’s just science! Their bodies are better looking, their faces have no wrinkles, and their muscles are super tight. In addition, certain parts of women are a lot perkier, if you know what I mean… And in her youth, she was definitely putting her body to good use, getting into all kinds of naughty situations. She once was rumored to have participated in a love triangle between her, Lindsay Lohan, and actor Wilmer Valderrama. Although she later denied any involvement, claiming that she and Wilmer were just friends, it was certainly something a lot of people fantasized about. All I can say is that if it did happen, Wilmer Valderrama must have been one lucky dude.
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