Photos of Taylor Swift, Through the Years

Photos of Taylor Swift, Through the Years


Taylor Swift has reinvented herself numerous times, just as she has released several albums. Initially, the musician debuted as a youthful, curly-haired teenager, but she has become a well-respected force in the music industry. Taylor Swift has composed nine albums, and her music has resonated with a broad audience. Previously a country singer who played an acoustic guitar, she has now expanded her repertoire to include electro-pop, alternative rock, and folk. You can see how the star’s appearance has evolved throughout her illustrious career by examining these pictures.

Fearless and Fancy-Free

Taylor Swift signed with Sony at the age of 14, becoming the youngest artist to do so. Nevertheless, she decided to go with Big Machine Records, an indie label. She initially released authentic country singles and eventually made history when she wrote and performed as the youngest artist to top the charts with “Our Song”.

Fearless, the second album by Swift, featured timeless tracks such as “Love Story” and “You Belong with Me.” The picture displayed here portrays Swift during the Fearless tour held at Madison Square Garden in 2009.

A Purple Princess Dress

In that time frame, Taylor Swift maintained her fondness and adherence to country style. Her signature blonde curls were always present and she often wore dresses that gave off a fairytale kind of vibe. During the 2008 Grammy Awards, where she attended for the first time, the singer of “Back to December” sported this look.


In the category for Best New Artist, Taylor Swift received a nomination, however, she was not the winner and Amy Winehouse took the award. The total earning from the Fearless tour exceeded $63 million, and the TV broadcast of the documentary called Journey to Fearless was presented in three parts.

Grabbing Those Grammys

The following year after, Taylor Swift appeared at the Grammys and managed to bag four awards, which included Best Female Country Vocal Performance, Best Country Album, Best Country Song, and Album of the Year. During the event, she also had a performance alongside legendary singer Stevie Nicks, performing her hits “You Belong with Me” and “Rhiannon”.

During this period, the well-known incident involving Kanye West took place. The musician disrupted Taylor Swift’s acceptance speech at the MTV Video Music Awards, leading to many years of jokes, disagreements, and speculation.

Debuting Straight Locks and Bangs

During the 2010 American Music Awards, Taylor Swift showcased a new hairstyle of straight hair and bangs, and also had cat-inspired eye makeup. Additionally, she was recognized with the award for Favorite Country Female Artist and also performed at the event.

In addition to creating and publishing her own albums, Swift also worked together with other performers. She co-wrote and appeared on “Half of My Heart” with John Mayer and “Two Is Better Than One” with Boys Like Girls. The artist additionally provided songs for Hannah Montana: The Movie and Valentine’s Day, where she also played a role.

The Speak Now Dress

Swifties, who are ardent supporters of Taylor Swift, can immediately identify the singer’s unforgettable dress worn during the Speak Now tour. The talented artist wrote and co-produced each song on her third album, which quickly became the top-selling digital album by a female artist. Some popular tracks from this album include “Mean,” “Sparks Fly,” “The Story of Us,” and “Mine.”

When the Speak Now tour proved to be a triumph, Taylor Swift, who was only 20 years old at the time, created two unique tracks for The Hunger Games soundtrack.

Country Girl

During Taylor’s initial appearances on the red carpet, she exuded a sense of innocence commonly attributed to those hailing from Nashville. The photo captured during her first attendance at the Academy of Country Music Awards in May 2006 is a prime illustration of her fashion choices during that period.

Her arrival as a young artist was demonstrated perfectly by the floral, flowy maxi dress, cowboy boots, and loose curls she was wearing. Though she didn’t win that year, she won the Top New Female Vocalist award at the ACMs the next year.


Back in 2007, when Taylor was still in the early stages of her career, she demonstrated that her abilities were not limited to singing and songwriting alone. She was also able to produce mesmerizing music videos. It was at the CMT Music Awards that same year where she was bestowed with the Breakthrough Video of the Year award.

It was evident that she had a strong belief in becoming a music royal in the future as she dressed in a magnificent sea-green outfit, matched with her gold curly hair, even in the past.

Diamonds Are a Girl’s Best Friend

Taylor donned an exquisite Marchesa dress along with a flawless pair of Christian Louboutin heels for the 2010 ACM Awards. Considering her four victories at the event, it can be concluded that lilac suits her well.

Apart from the music star who was wearing it, the real highlights of this appearance were the diamond adornments from Neil Lane, comprising of a set of diamond earrings, a diamond ring, and a glitzy diamond bracelet.

Bob Trial Run

Although she wouldn’t commit to the bob fully until her 1989 era in 2014, it seems like Taylor Swift did try out the look several times over the years. This faux-bob perfectly complemented her golden Zuhair Murad dress.

The outfit she wore to the 2011 Vanity Fair Oscars Party, which consisted of a glamorous and chic ensemble, was topped off with some glittery accessories such as a Jimmy Choo clutch and gold peep-toe heels. This marked the start of a more daring image for Taylor Swift.

Preppy and Perky Street Style

Apart from her glamorous red carpet gowns and bold stage outfits, Taylor Swift is popularly recognized for her everyday fashion sense. This snapshot captures the period of the musician’s fourth studio album – Red – when she resided in New York City and was actively engaged in her upcoming project.

The artist was frequently photographed departing from her residence wearing charming, preppy attire. During this time, Swift opted for playful prints, kitten heel footwear, and satchel bags as part of her fashion selections.

Striking in a Suit

In 2012, Taylor Swift changed her usual red carpet style by wearing a striking white suit at the MTV Video Music Awards. Swift is known for liking red lipstick and introduced this iconic look during this time period. Her love for red lips is evident in her music through various references.

Swift changed her style in the Red album, incorporating heartland rock and dance-pop genres, and featured the popular track “I Knew You Were Trouble.” When she performed, she frequently sported high-waisted shorts, a striped top in red color, and her hair styled in a ponytail.

Geometrically Inclined

Taylor Swift had a great year in 2012, as she achieved international success and received recognition at the MTV EMA awards in Frankfurt, Germany. Her stunning performance of “We Are Never Ever Getting Back Together” captivated the audience.

In addition, she returned home with three remarkable accolades: Best Female, Best Live, and Best Look. These awards were determined by global audiences instead of a panel of judges. Her numerous awards, together with her stunning J. Mendel geometric gown, made her truly standout.

So Punk Rock

If you’re a celebrity and you receive an invitation to the Met Gala, that’s an indication that you have achieved a high level of success. However, it’s not sufficient to simply attend the event. You also need to understand how to conform to the set theme and flaunt a remarkable attire.

Throughout the years, Taylor has demonstrated her aptitude for matching themes, unlike some other celebrities. Particularly impressive was her choice of a “Punk” J. Mendel dress at the 2013 Met Gala that aligned well with the rock-inspired vibes of her album Red.

A Fierce Red

When Taylor Swift reached the age of 24, she embarked on a global tour, following the massive success of her album Red. Her performances, which were named after the album, showcased her in distinctive red ensembles.

She donned this dress during her London performance, where she teamed it with a sparkly Union Jack shirt, an English flag, while sharing the stage with her close pal Ed Sheeran.

L.A. Preppy

During the period between the albums Red and 1989, Taylor adopted a bold appearance that was not only limited to red carpet events but also reflected in her daily routine. She moved from wearing cute dresses and vibrant designs to adopting more sophisticated and grown-up looks.

In early 2014, a photograph of the singer was taken during her stay in Los Angeles. Although she still appeared neat and stylish, her outfit – a button-up shirt and a braided black skirt – was more daring than the romantic dresses she used to wear as a teenager.

Going Into Battle

Taylor brought a popular fan favorite song with her to the 2014 Grammy Awards that she had perform before. The song titled “All Too Well” has been speculated to be about her ex-boyfriend Jake Gyllenhaal. Knowing this, Taylor prepared herself before performing it live by dressing up for battle.

According to reports, the silver Gucci dress that she wore looked like a more sophisticated version of chainmail, and it was said to be quite heavy. Taylor compared it to armor, and it had a very impressive and daunting appearance.

Plaid Coats and Beanie Hats

We have here another image of Taylor Swift in a relaxed attire, roaming the streets of New York City. On this occasion, the celebrity was clad in a plaid duffel coat, a woolen beanie, and a stunning purse with a vintage appearance. This was when Swift was in the process of creating her fifth album, 1989.

Swift collaborated with a team of producers, which included Jack Antonoff, to create her synth-pop-inspired record. This collaboration was successful, leading to an ongoing partnership between Swift and Antonoff. The album 1989 was positioned as Swift’s debut pop album.

Bobs and Blank Space

In 1989, Taylor Swift, who was 24 at the time, decided to change her hairstyle to a shoulder-length bob. At the 2014 American Music Awards, the singer sang her new hit single “Blank Space,” which pokes fun at her public image. During this performance, she fully embraced the outrageous rumors that had been circulating about her.

Additional tracks featured in this record are “Shake it Off,” “Bad Blood,” and “Wildest Dreams.” The associated concert series generated a revenue of $250 million, earning it the top spot for highest grossing tour of the year.

Channeling Fifties Fashion

This Taylor Swift outfit is absolutely amazing. Reminiscent of 1950s fashion, the singer wore a stunning pastel outfit. It’s one of her New York City street style outfits, consisting of a lemon houndstooth crop top and a pastel green fit and flare miniskirt.

In the year that Swift received the Woman of the Year Award from Billboard, she took down her music from Spotify and voiced her dissatisfaction with Apple Music. Apple responded by modifying their policy, which led to Swift collaborating with them.

Sparkly Sets and Slicked Hair

Taylor Swift chose a unique outfit for the 2015 MTV Video Music Awards red carpet. Instead of typical dresses or suits, she opted for a stylish two-piece houndstooth set by Ashish. It’s worth noting that Swift seems to prefer wearing matching two-piece sets and was seen sporting several around that same period.

The Ashish outfit worn by the singer complemented her sleek hair and smoky eye makeup. At the awards ceremony, Swift received the Video of the Year award for her song “Bad Blood” and also presented an award to Kanye West.

Pleats to a Premiere

In 2014, Taylor Swift adopted a classic style for the premiere of The Giver. She wore a Monique Lhuillier gown that featured color-blocked design and a draped, pleated skirt. The top part of the dress had a boat neck in red color, and she combined it with nude Casadei heels. Swift’s outfit resembled that of an old Hollywood star.

Given that Swift had donned her Ashish two-piece shortly before wearing this outfit, it’s evident that she is incredibly versatile when it comes to fashion. In this particular appearance, she made sure to include her typical red lipstick.

No “Bad Blood” on This Jumpsuit

Taylor Swift’s music video for “Bad Blood” was an immediate success due to the numerous celebrities who were featured in it, making it one of her greatest achievements. Thus, it’s not surprising that she achieved significant success after its release.

Taylor arrived at the 2014 Billboard Music Awards wearing an attractive Balmain jumpsuit and achieved a total of eight awards, including Top Artist, Top Female Artist, Top Billboard 200 Artist and Album, and Top Streaming Song for her hit “Shake it Off”. She returned home with these impressive accolades.

Art Deco Done Very Right

The 50th anniversary of the awards ceremony was made even more memorable by the presence of Taylor Swift, who had previously won the award for Entertainer of the Year twice, on stage to present the award.

Taylor looked stunning in a Julien Macdonald dress with an art deco style reminiscent of Gatsby. She had certainly made remarkable progress since she won the award for her Fearless album in 2009.

Color-Blocked Coolness

After her album 1989 did well, Taylor Swift received multiple Grammy Awards. At the 2016 event, when she was 26, she earned three awards including Best Pop Vocal Album, Best Music Video, and Album of the Year. It’s worth noting that this was the final time she went to the ceremony.

During her acceptance speech, Swift urged girls and young women to acknowledge their achievements, which was partially linked to the ongoing dispute between her and rapper Kanye West.

Bleach Blonde at the Met

In anticipation of her sixth album Reputation’s release in 2016, Taylor Swift made a bold appearance at the Met Gala where she was one of the co-chairs for the fashion event. The singer donned the same bleach blonde bob hairstyle that she had previously showcased on the cover of Vogue magazine.

Swift wore a custom-made Louis Vuitton dress with a unique cut-out design, complemented by dark lipstick and lace-up shoes for her public appearance. This was her final sighting in public for nearly a year.

Custom Looks on Tour

Swift’s debut single “Look What You Made Me Do” from her latest album “Reputation” reached the number one spot on charts across various countries. The album also features other hit tracks like “Delicate” and “Getaway Car.” During her upcoming tour, Swift is expected to surpass her own record for the highest-grossing US tour held by a female artist.

Jessica Jones was responsible for creating Swift’s wardrobe for the tour. During her rendition of “Don’t Blame Me” and “Long Live”/”New Year’s Day,” Swift donned a one-of-a-kind decorated dress.

Stunning in Silver Balmain

Taylor Swift used her album “Reputation” as a way of showing her independence and creativity. During that time, her fashion style became more daring and different from what she usually wears. She also experimented with her music and celebrity image. In the music video for the song “Look What You Made Me Do,” she dresses up as different versions of herself from her previous eras and has humorous conversations between each one.

The artist donned a stunning Balmain minidress in holographic silver for the 2018 American Music Awards, which she paired with thigh-high boots in the same color. Her presence at the event was akin to a dazzling disco ball.

Stunning Street Style

This is one more exquisite photograph of Taylor Swift’s street style in New York City. Unlike her grungy style in the past, the singer was seen sporting a bright pink sweatshirt with the print ‘NYC’. Although it appears to be something that tourists buy, the sweatshirt is actually from the luxurious fashion brand Balenciaga and costs a whopping $895. But considering she is a famous superstar, that’s not surprising.

Swift sported a fun appearance by adorning herself in Alexander Wang denim shorts, coupled with Guiseppe Zanotti boots and a Christian Louboutin black backpack. In total, this ensemble came at a considerable cost of almost $4,000.

The Colors of the Rainbow

After the triumph of both the Reputation tour and album, Taylor Swift promptly proceeded to embark on her next chapter. Lover surpassed expectations as all 18 tracks made it onto the charts, once again showcasing Swift’s exceptional talent. This seventh album features popular singles such as “The Man,” “You Need to Calm Down,” and “Me!”

The artistic style during the Lover era mainly consisted of vibrant hues and surreal aspects. During her various live performances, the artist adorned herself in rainbow-colored apparel featuring fringes and tie-dye designs.

Looking Regal in Ruffles

Taylor Swift showed up at the 2019 Billboard Music Awards donning a stunning lilac minidress with ruffles, created by Raisa and Vanessa. Her outfit seemed to reflect her country background to some degree. She completed her look with a studded ear cuff, a sophisticated up-do, and minimal makeup.

The studio album, Lover, became the top-selling album of 2019 and Taylor Swift received numerous awards for her work in songwriting, performance, and directing. However, she was faced with ongoing difficulties with her record label, which would ultimately worsen.

”Me!” And Lover

2019 not only saw the release of her seventh album Lover, but it also had Taylor releasing one of her most successful collaborations alongside Panic! at the Disco singer, Brendon Urie. The music video for the song features both artists decked out in pastels.

The album, like the single, was deemed a triumph and whimsical. That’s also a great way to describe Taylor’s fashion at the time as she shined in light and fun pinks and pastels.

Winning Big and Breaking Records

Taylor is clearly no stranger to winning big at award ceremonies. In fact, at the 2019 American Music Awards (AMAs), she walked away not only with five awards (including Artist of the Year) but also with the record of the most AMA wins.

She beat out Michael Jackson’s previous record. The late pop icon held a whopping record of 24 wins. But, with the AMA awards she received that year, she now stood at 28 wins!

Protesting in Style

At those same AMAs, Taylor performed in one of the most unique and iconic outfits, not because of its style exactly (although that too is as flawless as always). Instead, this look has been seen as an act of defiance.

The white jacket, adorned only with the name of her past albums has been seen as a protest against Big Machine Records holding the rights to the singer’s many songs. She also performed her song, “The Man” in this look.

Looking Classy for Cats

Swifties know that Taylor Swift is a cat person. The artist has three cats named Meredith Grey (after the Grey’s Anatomy character), Olivia Benson (after the Scandal character), and Benjamin Button (after the Brad Pitt character).

As a result, the singer was thrilled to land a part in the 2019 film adaptation of the musical, Cats. Swift played Bombalurina, sang “Macavity,” and contributed an original song, “Beautiful Ghosts.” For the premiere, the star wore this floral, floor-length Oscar de la Renta gown.

Perfect in Pastels

For the 2019 Time 100 gala, Taylor Swift returned to her princess-style “Love Story” roots. Wearing a stunning custom J. Mendel dress, the singer was pretty as a picture in pastels. The singer wore her hair in a tousled updo and kept jewelry to a minimum.

Most excitingly, the gown’s sleeves are detachable, so Swift removed them for her performance. As many fans do, Swifties started speculating about whether this floaty look was in reference to an upcoming album.

Always a Cover Girl

At the beginning of 2020, Taylor Swift appeared on the front cover of Vanity Fair. In the accompanying interview, the artist commented on her ongoing issues with her music label. All of Taylor Swift’s back catalog is owned by her recording label, leading her to rerecord all of her albums so that she owns her property.

For this photoshoot, Swift wore her iconic red lipstick and a range of ski wear. According to the article, the singer no longer wished to be “polite at all costs.”

Taylor Swift: Miss Americana

Another subject of the Vanity Fair article was Swift’s upcoming Netflix documentary, Miss Americana. For the premiere of the movie, Swift wore this gorgeous plaid suit to the Sundance Film Festival in 2020.

The houndstooth suit is by Carmen March, and Tay wore it with a belt, trench, and even matching shoes. The doc was directed by Lana Wilson, and followed several years in Swift’s life — from the Reputation tour to the release of Lover.

Doing it Herself

In 2020, Taylor Swift delighted fans with two surprise albums in quick successions. Folklore and Evermore were released five months apart and described as sister albums. They are both indie-folk records, making another stylistic departure from Swift’s earlier work.

For her performance at the 2020 Academy of Country Music Awards, Taylor Swift had to do her own hair and makeup. She opted for a Stella McCartney ensemble, including a sequined turtleneck, khaki pants, and black heels with gold chain ankle straps.

Beloved Across the Pond

Taylor’s international success is well-documented, but it’s still truly amazing to see how beloved she is all around the world. Not only that but she’s been honored internationally, too! In May of 2021, she received the Global Icon Award at the BRITs.

With the award she made history! Not only is she the first non-British artist to receive the award in the show’s history, but she’s also the very first woman to be given this impressive award!

Folklore and Florals

As the names of her two indie-folk albums suggest, Taylor’s outfits during her folklore / Evermore era were just that — folksy, floral, and flowy. 2021 also saw the singer take to the stage of the Grammy awards.

During the ceremony, she changed to a different flowy dress and performed a set including the songs “August” and “Willow” from atop a woodsy set. She also took home another Grammy for Album of the Year — her 11th!

All Too Well Velvet

Besides her two new albums, Taylor also managed to find the time in 2021 to re-record her previous album and release Red Taylor’s Version. The album also came with the 10-minute version of “All Too Well” alongside a short film.

Taylor adorned her own All Too Well premiere in a classy and suave dark purple velvet suit (alongside bright red nail polish). Taylor not only wrote the music but also wrote, directed, and acted in the short film.

A Sparkly Surprise

Thanks to the singer releasing many of her “Taylor’s Version” albums in recent years, fans of Taylor Swift who tuned in to watch the 2022 VMA were hoping to hear when Reputation would be getting the same treatment. Instead, fans got a massive shock.

The award-winning artist instead shared at the awards that she was about to release a brand new album at midnight. This turned out to be her newest album, Midnight — which became an instant hit!

This Glitter Is Gold

The last few years have been the most prolific in Taylor Swift’s impressive career. Not only did she release five albums in three years (three with brand new music), but she’s also released more new signals than the entirety of her career.

So, it’s no wonder she won the Artist of the Year award at the 2022 AMAs (alongside several other awards). She shined as bright as her many awards with a sparkly ‘70s-inspired jumpsuit by the Blonds. It seems her Midnight era is all about disco!

Gilded Glamour

Taylor really has been into the disco glitter look in recent years, and it definitely works for her. Surrounding the hype of All Too Well: The Short Movie, the artist has been making the rounds at film festivals.

She wore this impressive piece by Lous Vuitton to the premiere of her short film/music video at the 47th Toronto International Film Festival (TIFF). Fashion icon that she is, Taylor also matched her sandals, jewelry, and nail polish to the beautiful gown.

She’s Still Changing it Up

In total, Taylor Swift has over 10 Grammy Awards, an Emmy, 27 Guinness World Records, 32 American Music Awards, and 23 Billboard music awards. The lead singles from her recent albums, “Cardigan,” and “Willow” each topped the charts, and Swift released a self-directed concert movie, Folklore: The Long Pond Studio Sessions.

Taylor Swift has now rerecorded and released her second album Fearless, and continues to do so with her other work. Always keeping it fashion fresh, the singer wore this Monse deconstructed short suit to the 2020 NME awards.

While it may be surprising, some celebrities have actually gone through some pretty awkward phases. Don’t believe us? Just check out these celebrities that went through an awkward stage before they were famous.

Nicole Kidman

When people talk about Nicole Kidman, they talk about her radiant red locks and her beauty. Though her red hair is now her trademark, as a kid, she was tormented over being a redhead. To make matters worse, the red hair was super curly, so this really made her feel awkward. Thankfully, Kidman has learned to embrace her unique features.

Tina Fey

Tina Fey is one of the most well-respected comedians and writers in Hollywood. Though not always looked at as being beautiful, she is definitely stunning and talented. Even this comedic beauty went through a bit of a rough patch when it came to her teen years.

Like many of us, she suffered from acne and other skin issues. She also developed earlier than her peers, which made her the target of a lot of jokes. This made her teen years quite awkward.

Sarah Jessica Parker

When most people hear Sarah Jessica Parker’s name, we typically think of her role in Sex and the City. Not only did she play a relationship columnist and fashionista in the show, but Parker is known as a style icon off-screen too.

With several fashion lines and fragrances, Parker has a renowned sense of style. Looking at this photo, however, that wasn’t always the case. As a child, Parker displayed some less-than-fashionable bangs and wardrobe choices. What would Carrie Bradshaw say?


Eminem shot to fame in the late ’90s with his amazing flow and ability to be both funny and impactful with his words. Because of his fame, there were a lot of changes that would happen. And eventually, he wound up being a pretty good-looking guy.

But, when he was just a simple kid learning to rap in a trailer park he wasn’t always that confident. He was quite thin and gawky and often awkward in many situations.

Reese Witherspoon

Okay, so we’re sure that when you read this actress you were like there’s no way she went through an awkward phase. Reese Witherspoon is a classic beauty and down-to-earth as well. But she too had a bit of an awkward phase.

Growing up, many of her outfits were considered old-fashioned or frumpy. On top of this, she also needed glasses and her frame choice made it a little bit awkward and kind of gave her peers something to make fun of.

Bella Hadid

When you hear the name Bella Hadid you probably think of glamorous supermodels and fashion-forward trends. But even beautiful women who make money walking the runway have experienced some years where they may have been less-than-happy with their looks.

It seems that during her teenage years, Bella was kind of worried about her eyebrows and her weight. Though she looks fantastic to us, in her mind she felt that she was a little awkward. Judging by her confidence on the runway, it seems that she grew out of it.

Jameela Jamil

Jameela Jamil is not only beautiful but hilarious. Starring in hit television shows and being a social activist, many people have fallen head over heels for her. But this foreign beauty freely admits that she went through quite an awkward phase when she was a child.

Awkward phases don’t always have to do with your outward appearance, sometimes it’s socially awkward. It seems that this beautiful actress had a hard time making friends and has gone on record saying that she wasn’t the most beautiful child.

Gwyneth Paltrow

Most people would agree that their teens were an awkward time. It’s easy to see why this would be a strange time considering that your body is changing, and your personality is changing. Gwyneth Paltrow freely admits that her teenagers were quite brutal as she was clumsy and wore braces.

Some of the awkwardness though isn’t always natural – sometimes it’s self-inflicted. This is apparent by the fact that, at some point, she thought it was a good idea to shave the back of her head.

Alexandra Daddario

Sometimes, formerly awkward teenagers look for ways to show their former friends and peers that they have blossomed into a wonderful beauty. The stunning Alexandra Daddario is one of those people.

Apparently, she was quite nerdy as a child, and even though she had already started acting during her teens, it was still a rough time in her life. Eventually, though, it all worked out. Today, she’s considered one of the most popular and beautiful actresses in Hollywood.

Justin Timberlake

Justin Timberlake has been in the public eye since he was a child. That meant that he had to go through all of his awkward phases in front of cameras for all of us to see.

Not only did he struggle with skin issues and “iced” bleached hair, but he was also a little socially awkward in comparison to other people. Looking at his career and comfort in front of the camera, you would never think he went through an awkward phase.

Olivia Culpo

Supermodels and pageant winners are, of course, judged primarily by their beauty. This means that they often work really hard to have the perfect body and the perfect hair and that can be quite a challenge for some.

Olivia Culpo who was Miss Universe struggled with her weight when she was a kid. Not being super athletic, she found it challenging to lose it. That was until she hit a growth spurt and then everything corrected itself.


From her being a member of Destiny’s Child to a successful solo career, Beyoncé has become one of the most popular and famous artists in the world. Her beauty is beyond renowned, however, she wasn’t always the flawless beauty she is now.

In fact, she was a little awkward when it came to interacting socially with kids. Just goes to show you that even those stars that we look up to are simply human just like the rest of us.

Joe Manganiello

Many women and men across the globe melted when they first got a look at Joe Manganiello, and with good reason. Just looking at him with his broad shoulders and chiseled features you would think he was the most beautiful man in the world.

What many fans don’t know is that it took a lot to get there and quite a journey through a very awkward phase. Joe has told many people that he was kind of a skinny kid who really loved mullets. That is one awkward phase!

Matthew Perry

Matthew Perry is not typically known for his looks, but he is cute and has quite a following. Thanks to his impeccable comedic timing and charisma, Perry quickly became a fan-favorite on Friends.

Though he may be one of the actors we all completely believe had an awkward phase, most fans are willing to overlook that. It appears that in his early teens into his early 20s, he went through quite the gawky stage.

Matthew Lewis

It’s probably the hardest thing when you have to go through your awkward phase in front of cameras. The kids that were in the cast of the Harry Potter franchise had to do this. And some awkward phases were a little rougher than others.

Take for instance Matthew Lewis, who played Neville Longbottom. He was the adorably dorky heavier-set child who eventually grew out of his awkward phase. Today, Lewis is considered one of Hollywood’s biggest rising stars.

Kristen Stewart

Kristen Stewart has been acting for quite a while. And though she’s now looked at as one of the hottest actresses on the screen, she also went through her awkward phase. Unlike many other celebrities, the awkward stage actually happened a bit later.

It seems that in her late teens she found herself becoming more and more awkward in front of people. She actually called it a terrible and very weird time in her life and career.

Sandra Bullock

Sandra Bullock is considered one of the most well-respected actresses in Hollywood. Starring in everything from comedies to dramas, this actress has carved quite a niche out for herself. The brunette beauty definitely is on many peoples’ heartthrob list.

But Sandra is really honest when it comes to the evolution of her beauty. It appears that when she was younger she really loved barrettes and they were always in her hair. This kind of made her stand out a little bit amongst her peers.

Taylor Schilling

It’s hard to believe that this Orange is the New Black star actually had rough teenage years. Looking at her now all you see is beauty and grace, but apparently, she had quite a rough time both at home as well at school.

She was tall for her age and had very short hair and glasses which made her stand out. It also made her the target of a lot of bullying.

Sara Sampaio

Many people look at Victoria’s Secret models as being the most beautiful women in the world as they walk down those runways. But not all of them started out looking so fantastic like model Sara Sampaio.

Just like all of us, she went through phases and fads and some of them didn’t play out so well when looking back in photo albums. Sara made some questionable fashion choices and that left her with some pretty awkward memories.

Dwayne Johnson

The Rock, now known better as Dwayne Johnson, is one of the biggest stars in Hollywood. Not only is he good-looking and well-built, but he’s also funny and humble. Surprisingly, though, his look and physique didn’t come to him naturally.

In fact, when he was in his youth and into his teens he found it very difficult because of not only acne but his overall appearance. Thankfully, he has embraced his physique and is now one of the most in-demand action stars.

Zooey Deschanel

There are kids that start their youth out being a bit heavier-set and then after they reach teen years and hit puberty, they begin to lose their “baby” weight. Looking at Zooey Deschanel you would never think that this young woman suffered from that problem.

The truth is that when she was a teenager, she was a little bit on the heavier side. Her body issues put her in a difficult situation and made her feel quite awkward when dealing with her peers.

Kim Kardashian

The Kardashians have become fashion icons over the past years. The leader of that crew has always been Kim and she is a beauty beyond compare. With her curvy figure and her beautiful skin, it would be hard to believe that she ever went through a rough period.

But apparently, when she was in high school, she opted to cut her hair really short. At the same time, she was also struggling with her weight. This combination made it quite awkward and made her feel a little out of place.

Rachel Weisz

Sometimes the awkward phase is not so much about the personality or even the way they look, but rather the fashion choices they made. Rachel Weisz is one of the most stunning actresses out there, but during her teenage years, she opted to wear some interesting apparel.

It seems that as a teenager she thought it would be cool to wear men’s suits and red lipstick. While this style would look nice on an adult, it led to the actress being ridiculed for it as a child.

Kerry Washington

Following your fashion icons is something we all do. Most of the time you’ll take something that they do and kind of put your own spin on it, but sometimes you copy it completely. This is what happened with Kerry Washington when she was younger.

She was a big fan of Punky Brewster and chose to use this as her style to set herself apart. Unfortunately, not everybody felt that this was a great look and it led to some very awkward moments.

Blake Lively

Not only does Blake Lively have a thriving career in Hollywood, but the beautiful actress is also considered a fashion icon and the source of a lot of heart-fluttering whenever she appears on the screen.

But when she was in her teens, just like everybody else she had some teeth that needed to be straightened and a little bit of acne. On top of that, she liked to match her eye shadow with her pants! We can imagine this leading to some pretty interesting looks.

Lena Dunham

Lena Dunham has had several different phases where it became a little awkward. Not only when she was a kid but also as an adult. It seems as if the paparazzi like to catch her when she is not at her red carpet-level look.

Growing up she was a cute kid with curly hair. As an adult, she has made her way into being quite the proponent of awkward fashion with most of her looks falling into the “love it” or “hate it” category.

Kristen Wiig

Kristen Wiig is a Saturday Night Live alum who has made quite the name for herself. Not only is she hilarious but she is absolutely gorgeous. It would be very shocking to find out that she had an awkward phase.

But she does admit that she didn’t always get it right when it came to her fashion sense. There was a time when she was younger than she was super skinny and loved a good perm.


The word supermodel leads us all to believe that they came out of the womb looking perfect and walking down the aisle with the right walk. But models like Iman are human and go through the same growth cycles that we all do.

It seems that the iconic model went through a time when she was super skinny and taller than everybody else. This makes for a great supermodel but maybe not so much for a teenager.

Debra Messing

Sometimes, when it comes to awkward phases, we don’t realize we’re in them until we look back at the pictures and it suddenly hits us. This might be what happened to actress Debra Messing because though she is a stunning beauty now, it seems that when she was in her late teens she didn’t feel like such a beauty.

Apparently, she liked permed mullets and tweezing her brows a little bit too much. We can understand why she thinks that this was an awkward phase.

Andy Cohen

Andy Cohen might be a handsome and funny guy today, but he wasn’t always so put together. It seems that in high school and in junior high he had some pretty awkward years just like the rest of us.

Not only did he wear glasses but he opted to grow his hair out so he could wear a ponytail. Though that might have been the trend at the time, it definitely didn’t look right on him, and according to Andy, it led to some pretty awkward moments.

Olivia Munn

Looking at Olivia Munn today you would think that she was always beautiful. The conundrum with Olivia is that not only is she beautiful, but she’s funny as well which makes her shine even more.

However, as a teen, she struggled with some issues with her body and some skin issues. Thankfully, Munn has become confident with herself and her obvious talents.

Ryan Seacrest

Though Ryan Seacrest is known for his hosting skills and his voice, he is also quite handsome as well. He is always put together and looks like he knows what he’s doing when it comes to fashion.

It took years for him to be able to get to this level and it had several awkward phases as well. During his youth all the way into his teens, Ryan struggled with his weight. Eventually, he took it upon himself to lose weight and get healthy.

Avril Lavigne

Avril Lavigne started out as the epitome of a skater boy’s crush and wound up evolving into a beautiful young woman. Before she hit it big, though, she was just a typical teenager like the rest of us.

This meant that she went through some awkward phases like haircuts that really didn’t work for her and having to wear glasses. But like with everything else, evolution happens and now she is quite confident with her appearance.

Jamie Foxx

Jamie Foxx is definitely one of the most popular actors in Hollywood. Going from his comic beginnings all the way to his action-packed and award-winning career of today, you would never imagine that he struggled with his image.

But as we’ve seen before, this actor had to go through puberty just like the rest of us. This left him with body issues as well as maybe some questionable hairstyle choices. This awkward phase seems to be far gone compared to the confident man (and star) he is today.

George Clooney

George Clooney is often considered one of the most attractive stars. His perfect face and his iconic eyebrows mixed with his salt and pepper hair have made him quite the heartthrob. But those eyebrows don’t weren’t always working for him.

In fact, when he was a teenager he went through some phases where not only did the eyebrows make him stand out, but he also wore glasses and had some questionable ideas of what a good hairstyle was.

Kelly Clarkson

Kelly Clarkson’s voice is magical and her effervescent spirit has made her a popular daytime talk show host. Though it took her years to get to this level of confidence just like many of us.

She went through several awkward style phases including everything from being a little bit overweight to braces. Thankfully, the star has embraced her own unique style and look.

Lil Jon

Okay so Lil Jon is not everybody’s cup of tea, but he is definitely a good-looking and talented guy. Looking at the fashionable musician today, you would never imagine that he would have had such an awkward phase.

The rapper actually went through quite an awkward phase. Where he was wearing very large glasses and had a very unique beard situation going on. We can’t imagine that the confident celebrity we see today, once went through such an awkward phase.

Rashida Jones

Rashida Jones is a hilarious and stunning beauty. Many people look up to her, not only because of her beauty but because of her talent as well. Even though she’s a stunner, there were definitely a couple of times where she felt awkward.

In her youth, she was a bit of a curvier girl. That was until she hit puberty and became more confident with her body. This, coupled with other things, often made her feel very awkward (though we think she was stunning even then).

Paul Rudd

Paul Rudd has that nerdy good look vibe. This may be because he’s a comedian and often those types of actors tend to have that vibe. But when he was younger, all he really had was the nerd vibe according to him.

It seems that Paul found himself always being a bit on the nerdy side. That could be because he chose to wear a mullet and tried as hard as he could to fit in with the rest of the crew. Thankfully, he always had that famous adorable smile!

Matthew Gray Gubler

Matthew Gray Gubler is definitely one of network television’s most famous (and admired) faces. Many people find him super handsome and well put together. But if they had seen him when he was a teenager they might not feel the same way.

He had quite a few awkward moments including some questionable fashion choices and a love for card magic. We can’t imagine the combination of turtlenecks and magic making him a hit during his high school years!

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Mute Maven


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