Demi Lovato is a Grammy-nominated singer and actress. The celebrity first got her start on the Disney Channel, thanks to her breakout role in Camp Rock alongside Joe Jonas of the Jonas Brothers’ fame. It wasn’t long until the star scored her own show, Sonny With A Chance, and became a figure in mainstream pop culture.
Since kissing her Disney days goodbye, Demi’s career sure hasn’t slowed down. She released her first album, Don’t Forget, in 2008, and has followed it up with five more albums, released in 2009, 2011, 2013, 2015, and her most recent record, Tell Me You Love Me, released in 2017. Demi later took her musical talent to TV where she acted as a judge on the American version of The X Factor from 2012 and 2013 and had a recurring role on Glee. She released her book Staying Strong in 2013, and last year released a YouTube documentary detailing her journey to fame.
Since she’s no newbie to Hollywood, it’s no surprise that Demi’s style has changed just as much as her career has. Check out these photos that show how much of a style evolution Demi has undergone to make her into the edgy pop star we know and love today. Which of Demi’s looks is your favorite?
20 Then: A Disney Darling
Fans know that Demi Lovato first got her start on Disney Channel, with her breakout role in the made-for-TV series Camp Rock and her subsequent show Sonny With A Chance. Demi looks almost unrecognizable in this throwback photo of herself at a Disney event, from her modest plaid dress to her chocolate brown hair.
“I wouldn’t start out that young if I could do it over again,”
Demi told Variety about being a child star in 2017. “[However] I don’t regret anything. It was difficult to transition from a child star to transforming into a mainstream artist. It’s something that is very challenging.”
19 Now: Mad For Plaid
There’s no denying that Demi loves plaid and leather, and that hasn’t changed during the years. The only thing that’s changed is that the starlet has learned how to make her edgy style more sophisticated and grown-up, as evidenced by this fashionable outfit.
On this day, Demi stepped out in a schoolgirl-inspired mini skirt that she totally pulled off. She paired the plaid skirt with a white button-down and matching red pumps, adding a bit of rock n’ roll to this otherwise modest outfit. The singer’s choppy, short ‘do added to the overall edgy vibe of the look, while her red lipstick perfectly matched the rest of the outfit.
18 Then: Red Carpet Debut
When many fans look at photos from Demi’s days on Sonny With A Chance, they notice how much tinier the singer-actress was, just like this red carpet photo proves. Demi has since admitted that she struggled with her image while starring on the hit show, and has been more open about her challenges in recent years.
“No longer depriving myself of treats (in moderation) and I’m not gonna lie, I put on a couple lbs since I’ve given up dieting,” Demi tweeted to her fans earlier this year about giving up dieting completely.
“BUT I’ve given up the chronic stress of what I eat because I don’t want to set that example for my fans.”
We’re glad she seems to be in a better place!
17 Now: A Little Bit Of Leopard
Demi never looked better than when she recently walked the red carpet in this figure-hugging outfit! The star rocked an olive green dress that showed off her curvy frame, while she perfectly accessorized with touches of leopard and a smart trench coat. Her short ‘do added to the sophistication of this stylish look.
Many fans have pointed out how much happier and more comfortable Demi appears in photos- and she credits that to finding happiness within herself. "I don't let anyone's insecurities, emotions, or opinions bother me. I know that if I am happy, that's all that matters to me,” she told Seventeen Magazine in 2011. “And it's okay to be selfish like that sometimes when it comes to your well-being. Do what makes you happy, and don't care what others think."
16 Then: Finding Her Footing
Demi totally didn’t look like her usual edgy self when she rocked this blue maxi dress on the red carpet… over 5 years ago!
The celeb traded in her signature locks for a blonde ‘do, which makes her seem unrecognizable.
Despite her gown having touches of leather and gunmetal accents, Demi didn’t look very comfortable in this trendy outfit (if the look on her face is any hint).
“You have to find your identity,” Demi told Variety about navigating Hollywood at such a young age. “For so long you’ve been molded into something and now you’re expected to figure out who you are very fast in front of the entire world.”
15 Now: A Matching Maven
Hands-down one of the best outfits Demi has ever rocked is this stylish two-piece ensemble! The starlet looks ravishing in this black-and-white outfit, which featured a voluminous swing skirt and matching crop top. Demi’s half-up topknot added some edginess to the look, while her patent heels kept all attention on the eye-catching pattern.
"What I would say to somebody that’s struggling right now is try to find the gratitude," Demi told E! News this past year about accepting yourself for all of your flaws. "It’s so important that you try to find gratitude in your life, and focus on the positive things.” You go, girl!
14 Then: Glowing Like A Goddess
Several years back, Demi proved that gold is totally her color when she stunned in this Grecian-inspired dress on the red carpet. The singer’s hourglass figure was on full display in the stylish dress, while her effortless hair and makeup matched the golden vibes of the look.
Despite how beautiful she looks in this photo, Demi has revealed she wasn’t nearly as confident in herself back then as she is now.
"I used to think that confidence came from what other people thought about me, and boys and everything else,”
she shared with Seventeen Magazine in 2014.
The celeb added, “But now I realize that confidence comes from what I feel about myself, and reassuring myself that I can do whatever I want and be whoever I want.”
13 Now: Loving The Leopard
Most people will tell you that pulling off head-to-toe leopard print is a huge fashion risk… but if anyone can pull it off, it’s clearly Demi!
This past year, the celeb proved she’s not afraid to rock a bold print when she stepped out in this dramatic leopard print gown. From the deep V-neck to the high slit to the voluminous sleeves, Demi was looking more fashion-forward than ever, and we totally think it worked in her favor.
On the topic of confidence, Demi once said, Popsugar reports, “If you don't love yourself for your flaws and imperfections, you can't expect anyone else to either.” Word!
12 Then: The Bold And Beautiful
Many fans will remember when Demi first began to dress edgy, like when she showed up to the 2012 Teen Choice Awards in this bold outfit. The celeb was suddenly trying to turn-around her goody-two-shoes Disney image for a louder, edgier persona, and she totally nailed it in this sequined-and-feathered outfit.
Demi attributes finding her confidence to being able to dress more fashion-forward.
“We are each made differently, so find whatever flaw or imperfection you have and start embracing it because it's part of you,” Demi wrote in her book Staying Strong, Pop Sugar reports. “Be proud of your originality. There's no one else in the world that's like you."
11 Now: Oversized But Chic
For many years, we’ve been used to seeing Demi show off her figure in tight, outfits. But recently the star has been loving oversized clothing that still shows off her edgy sense of style, without being too revealing.
In this outfit, in particular, the celeb looked stylish in a baggy denim jacket that she accessorized with bold hoops and a high ponytail. Who knew oversized clothing could be so chic!
"There needs to be more variety on television so young girls growing up don't feel pressured to look one specific way,” Demi has tweeted about needing more diversity in Hollywood, Pop Sugar reports- and we totally agree. “Tall, thin, curvy, short, whatever you are, you are beautiful."
10 Then: Almost Grown Up
Nowadays, Demi is confident in her edgy sense of style and proud of her gorgeous curves. But this photo proves the starlet didn’t always know who she was amongst the hustle and bustle of Hollywood.
The celeb looked slightly uncomfortable in her modest red carpet look, which featured a long-sleeve black dress and a vintage-inspired ‘do.
It’s easy to see Demi’s love for all things edgy peaking through thanks to her copious amounts of black eyeliner and metallic nail polish.
But it was a while before Demi started dressing more like herself nowadays.
And we’re sure glad Demi has found what style works for her now!
9 Now: Military Mama
Leave it to Demi to style a military jacket in the chicest way possible!
While on her way to an event, Demi looked stylish in a green army jacket, which she dressed up thanks to her matching, leather two-piece look. Her tight pencil skirt showed off her enviable figure, but the knee-length hem and oversized army jacket balanced off the amount of skin she was showing.
Demi kept the rest of the look sophisticated with studded heels, a pair of Ray-Ban glasses, and her short hair in a chic style. Who knew it was possible to look this good in a military jacket!
8 Then: Beginning To Edge Out
Nowadays, it’s a sight to see Demi leave the house in any sort of outfit that doesn’t incorporate any sort of leather into it.
But, back in 2012 when this photo was taken, the star was just beginning to branch out in terms of her style.
For a Topshop event, Demi decided to go a bit edgier with her look by adding a leather mini skirt to the outfit. She still kept the look professional and modest with a white blouse and peep-toe heels, while her blonde curls added to the sweetheart vibes we’re getting from this outfit.
If anything, this outfit was a hint at all the edgier looks that were to follow Demi in the coming years!
7 Now: Pink Hair, Don't Care
One of Demi’s signatures is her stunning, dark hair. But a sign that the celebrity has become more adventurous and confident in her style is that she’s been experimenting with less natural hair colors in recent years.
It wasn’t too long ago that Demi was rocking pink hair instead of her traditional dark locks. In this photo, the celeb styled her bold hair with a graphic t-shirt, ripped jeans, and a plaid beanie to give us total punk-rock vibes.
Even though she got a bit of hate for her wild hair color choice (even though we’re obsessed with it), Demi’s best advice is to just tune the haters out. "There's gonna be haters, but don't let them affect you. Don't let them take away a part of you,” she said, as Pop Sugar reports.
6 Then: A Priceless Pompadour
Demi has rocked tons of cool hairstyles throughout the years, but no one could forget the phase she went through when she was always caught rocking bold pompadours on the red carpet. Back when she was a blonde, Demi rocked this edgy hairdo alongside an orange mini dress and a contrasting leather jacket. This girl can pull anything off!
Demi’s best advice for achieving confidence in your self? Always believe in you!
"You can turn your life around. You can go through [tough times] and back. It is possible. Never underestimate yourself,” Demi tweeted back in 2014, Pop Sugar reports. “I believe in you." And we believe in her sense of fashion!
5 Now: Better In Black And White
Although Demi still rocks a lot of bold and fashion-forward looks, she also chooses to wear more classic silhouettes and colors. While attending a recent We Day, the celebrity showed off her petite figure in a black-and-white ensemble consisting of tailored trousers and a modern, strapless top.
"Life is precious and it's what you do with it that keeps you alive on the inside. It's not enough just to live and take that gift for granted,” Demi has said about finding peace within herself, which has undeniably influenced her fashion choices, Pop Sugar reports. “Each one of us has fears, but the more we work to overcome them, the more we are able to enjoy our lives."
4 Then: It's Always Sunny
Though the Demi of today tends to stick to darker colors and leather, there was a time the singer-actress was known for rocking bright outfits, like this time she showed up to the 2011 Teen Choice Awards in an electric yellow dress.
The star was absolutely glowing in the adorable mini dress, while her wavy hair and glowy makeup complimented the fresh look.
Despite looking radiant, Demi has admitted this was a time in her life when she was most struggling with herself. "It's going to be okay. No matter how hard your rock bottom is, you can rise above it and you can come back,” the star has since said about rising about her challenges, Pop Sugar reports.
3 Now: Ravishing In Red
Red is totally Demi’s color!
The singer looks gorgeous while strolling the streets in this black and red mini dress. Her blue-dipped hairstyle and half-shaven head gave the girly dress a rock n’ roll sort of feel, while her oversized Celine purse and pointed stilettos kept the fashion-forward look sophisticated and pulled-together.
When this photo was taken, many fans pointed out how much slimmer the celeb seemed. But Demi’s only advice to losing weight is to be patient and do it the right way. “If you want to lose weight, you've got to work for it. If you want to get stronger, you've got to work for it. Any other way isn't going to be healthy, and it's not going to last,” she said to Fitness Magazine.
2 Then: She's Gone Rocker
Demi was totally embracing her edgy sense of style when this photo was snapped almost 5 years ago.
The celeb stepped out in a boldly printed dress that she accessorized with a leather vest and spikey jewelry. Her top-knot added a feminine flair to the loud outfit.
These days, Demi might not opt for such a floral and colorful print but you can definitely see how she was finding her way towards the edgy fashionista she is today. I'm sure we can all relate to the struggle of developing our own sense of selves and identity!
1 Now: Bomb In A Bomber Jacket
Years ago, Demi would rarely show up to a red carpet event in anything less than a fancy mini skirt. But, nowadays, it’s clear to see the celeb is more comfortable in her clothing choices. Like this picture shows, the star isn’t afraid to show up in a casual bomber jacket and black slacks- and she totally slays it!
Demi admits that she’s come a long way- both in terms of her fashion choices and personal struggles- but she’s only looking towards the future. "I know my past will always be a part of me, but I don't want it to define me,” the singer told Fitness Magazine. “I'm excited to live in the present and looking forward to the future."
References: Seventeen Magazine, E! News, Popsugar, Fitness Magazine,
