Admit it, you were a big fan of Disney’s High School Musical franchise. It’s nothing to be ashamed of. You and 7.7 million people all tuned in during its premiere back in 2006. Of the entire cast that ended up successful (thanks to the movie franchise) was Ashley Tisdale, who starred as Sharpay Evans. Tisdale went from starring in Disney movies and TV shows like The Suite Life of Zach & Cody, to recording albums and even working as an executive producer.
The blonde beauty has had (and continues to have) a very promising career in Hollywood. She’s worked in the business since she was a little kid, so we’ve practically seen Tisdale grow up before our own eyes. However, Tisdale has had some very interesting choices of wardrobe since starring on the Disney network. From walking red carpet movie premieres in a jeans-and-skirt combo to wearing poodle slippers, Tisdale has had very questionable fashion choices.
Thankfully, the star hasn’t taken the criticism too harshly about how she used to dress, and her wardrobe has drastically changed… for the better. We’ve got eighteen photos that show just how Tisdale’s fashion game had left us all wondering who dressed her and photos that prove she’s said goodbye to her Disney style once and for all.
18. Was The Skirt And Jean Combo Ever A Thing?
During a movie premiere, Ashley Tisdale rocked this little number, and it looks like she apparently couldn’t decide on whether she wanted to wear a skirt or jeans, so she chose both! This was definitely a very early 2000’s moment, especially with her boot-cut jeans and cheesy logo t-shirt. Even her piano purse is making us question her taste in fashion. Hopefully, she didn’t hire a professional fashion stylist to dress her at this premiere for Disney’s Ice Princess in 2005. We were going to give Tisdale a break here because this is exactly what looks like a teenager would throw on, but she was actually already 20 years old at this premiere!
17. Continues Her Skirt-Over-Pants Theme
Can someone tell Ashley Tisdale that the skirt-over-pants thing is not a fashionable thing? Was it even popular back in the 2000’s? Her outfit in this photo isn’t too severe, but it looks like the actress wanted to add something else to her all-black look. A bright-colored purse might have worked instead, but Tisdale had to add a little flare to her wardrobe choice by putting on this white (very short) skirt that doesn’t even look like it would cover her behind if she wore it alone. At least her smile saves her in this photo because this outfit is just tragic.
16. Let’s Not Forget That Time She Wore A Feather Boa And Slippers To A Film Premiere
During the DVD release party of The Princess Diaries 2, Ashley Tisdale came out looking like she was ready for her closeup. With a pink feather boa wrapped around her neck, slippers with poodles on them, and a pink Hello Kitty blindfold on her head, her look totally confused us. Was she ready for a pyjama party or was this star ready to take some glamour photos? This look is definitely a winner when it comes to the top fashion mishaps this singer has made during her career. Comfort is one thing, but anywhere where cameras are around, this look is totally wacko.
15. A Total Fashion Flop
There is a lot going on in this photo, and it’s literally all on Tisdale. This photo looks like she’s at yet another movie premiere and she decided to yet again make heads turn for all the wrong reasons. Let’s first ask ourselves how she found these hideous moon boots that match her outfit? This outfit looks like something Sharpay Evans would wear. Tisdale admitted in an interview that she kept some of her High School Musical character’s clothing. “I have [Sharpay’s] whole first wardrobe from the first [High School Musical] movie,” she said, adding, “Because I was just so into clothes, for some reason, I thought I’d wear her clothes again, which I never did.” That’s a little hard to believe from looking at these photos so far.
14. Committed To Dressing Like Sharpay Evans Even Off Screen
Only Tisdale can rock a baby blue nightgown with jeans and metallic cowboy boots. She admitted that she loves to play around with fashion, and we can definitely tell based on these questionable photos. She’s stated that she helped invent some of Sharpay’s style and was so committed to the role that she actually tried to dress like her alter ego. “I invented some of [the outfits] in the movies … I would take a skirt and wear it as a tube dress, and it became a staple outfit, which is so crazy,” she told PeopleStyle in 2015.
13. Thou Shalt Spend On Tacky Clothing
Where do we even begin with this fashion mistake? From the blue shirt with the saying “Thou Shalt Spend” to the matching blue socks and Ugg boots, and finally deciding that blue eye shadow would make her look complete, we are at a loss for words. Her look is something a pre-teen would wear, and we’re sure she’s far from that age in this photo. Did her fashion stylist shop at the Limited Too for her? Let’s also mention how dreadful that fury pink bag is. Thankfully, we’ll see her fashion choices change later on to more subtle and simple looks.
12. Obsessed With Her Alter Ego
Ashley Tisdale admitted that she invented many of the outfits for Sharpay Evans for the High School Musical films and even continued to dress like her alter ego to get into character. However, her bright pink, glamorous wardrobe is something she should have left during filming. We understand that it’s important to get into character for a film, but too much pink can obviously be a bad thing. Also, we never got to see Tisdale’s personal style back then, which probably can’t get any worse from what she was wearing while at red carpet events.
11. Tinker Bell Comes To Mind For This One
Ashley Tisdale’s dress looks more like a Tinker Bell costume she purchased at a Halloween store than a dress you would wear to a red carpet event. Even her purse, with a photo of a girl that looks like a fairy, just makes it all scream Peter Pan and fairy dust. It’s amazing how her fashion style has changed over the years. Tisdale was one star that wasn’t scared of trying something new, even if it meant wearing multiple types of bottoms at once. At least she created her own style and didn’t copy other looks from celebs, even if they were a little questionable.
10. Tisdale’s Go-To Look
Okay, so we already saw two or three of Tisdale’s skirt-over-pants-themed outfits, and we just can’t believe how much she thought it looked good that she would try the look again! This time, Tisdale opted for an all-white look and just had to layer her white pants with a white bohemian-styled skirt on top with a large gold belt. This look was also one of her Sharpay-inspired fashion go-to’s. “I created the character … through her clothes. I wore the dress with pants underneath and a belt and it was this one specific moment in [High School Musical]. It’s so funny how the stuff that you have so much fun with in a fitting actually happens and it becomes a part of a culture phenomenon, it’s so weird,” she said. Hey, at least she’s having fun with it!
9. Enjoys Experimenting With Her Clothing
As you can tell, Tisdale loves to play around with her look, and we give her a lot of credit for it. Not everyone can pull off some of the looks we’ve already shared. During the 2000’s, many celebs were experimenting with fashion, and Tisdale was definitely one of them. Here, she played around with mix-matching colors and prints. The former Disney star wore a satin green Japanese dragon blazer with a Jem band t-shirt and gold beret that would most certainly be on the worst-dressed look now. The 2000’s seemed a lot more forgiving when it came to fashion and style.
8. Still Looks Childish
Ashley Tisdale certainly has a unique taste in style. Here, she isn’t wearing skirts over pants or arriving to movie premieres in slippers. However, the outfit isn’t doing her any justice. We can’t see Tisdale’s individual style at this event and her outfit is pretty tacky with all the exaggerated accessories like the gigantic gold necklace and the weird chain attached to her pants. Her clothing style still seems childish here and walking around with a large Louis Vuitton doesn’t make you look more adult. Who carries such a big purse to a movie premiere anyway?
7. Doing Bohemian All Wrong
Maybe if she had taken off the jeans and white t-shirt underneath her frilly bohemian dress, the outfit could look a little more fashionable, and less questionable. However, this entire outfit looks like a big mess. Again, we can see Tisdale trying to embrace her funky style, but it just doesn’t work well for her. She even matched her gold flats with her slouchy bag. There is too much going on here, and this is yet another fashion fail for the young actress. We love a person who experiments with their wardrobe, but it doesn’t mean putting everything on all at once.
6. Grabbing Coffee With Her Beau In Pyjamas
Some people would never get out of the house in their pyjamas, since it basically is a fashion faux pas, and then there are others, like Tisdale and her husband, Christopher French, who just don’t really care. The two literally look like they just got out of bed and decided to grab a bite to eat or coffee before their day begins. We’re pretty sure not everyone wants to know what French is wearing to bed, and those snowflake pants aren’t helping him one bit. And isn’t Pink for teenage girls, Ashley? This couple needs to get it together.
5. Making A Fashion Comeback
We think you’ve seen enough of Ashley’s fashion mistakes, so let’s give the girl a break and look at how much she’s evolved since her teenage years. This simple motorcycle jacket and black jeans look appears so effortless and makes Tisdale look very chic. We really love how the outfit looks on the star, and we’ve noticed that her style has become a little more edgy over the past years. There are no large accessories here and definitely no pink slippers at this event! Tisdale is doing everything right in this photo. Finally, she gets it!
4. Embracing Her Edgy Style
With a cute puppy in hand, Tisdale is killing it in this outfit. She completes her all-black attire with this lovely camel coat and Hermes belt. We can definitely tell Tisdale is more on the edgy and rock-and-roll side when it comes to her fashion style. From wearing Sharpay Evans’ favorite pink and frilly outfits to this all-black ensemble, we’ve seen a huge change in Tisdale’s style (for the better). Her look here looks ultra comfortable, but she manages to make it chic. Rocking Chanel sneakers, too? We’re all pretty jealous.
3. Looking Like Her Age
Finally, Ashley Tisdale is dressing her age! The 32-year-old actress looks amazing in this photo, and we love the spiked flats! Tisdale is wearing a simple white t-shirt that reads “Celfie,” wrapped a button-up around her waist and wears a pair of what look like boyfriend jeans. With her hair up in a messy bun and large, red sunglasses, this look looks effortless but really put together. We can definitely see Tisdale’s fashion style here and just how much she’s changed from wearing tons and tons of pink.
2. Taking A More Adult Approach
How stunning does Ashley look in this two-piece crop top and wide-leg pants? She wore this number at the Tony Awards in 2015 and had all eyes on her. With her hair pulled back and a gold choker as her only accessory, Tisdale looked on top of her game. The pieces were designed by Solace London, and Tisdale was one of many presenters at the award show. We can still see the actress playing around with fashion, especially in this number. She has the perfect body type to wear this, and the pants make her look long and lean. We are big fans of this one, Ashley!
1. On Her Fashion Game
This look is by far Ashley Tisdale’s best ever. The High School Musical star showed off all her goods in this beautiful dress with fur coming off the shoulders during the Elton John AIDS Foundation Academy Awards Viewing Party in 2016. From her hair all the way down to her shoes, Tisdale looked absolutely stunning (and she definitely looked her age). Can you believe the impressive fashion evolution of Ashley Tisdale? From wearing obnoxious pink dresses and skirts over pants, Tisdale has learned a lot from the fashion world. She is looking better than ever now!
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