Ashley Tisdale may be known for her Disney roots, but she’s also consistently made her mark on the casual style scene, particularly in maxi dresses.
From comfy airport looks to boho-chic red carpet moments, she’s served up plenty of maxi magic (and a few missteps). Below, we’re breaking down some of her most talked-about maxi dress outfits—and what worked (or didn’t) about each one.
Ashley Tisdale’s Printed Maxi Dress Look: Chic or Too Busy?
Ashley Tisdale is no Olivia Palermo, but the girl can dress—that much we know. In April 2014, however, we found the former Disney cutie in rather unusually put-together attire while running errands in Beverly Hills.
Ashley Tisdale waves while wearing a printed maxi dress and a chic ivory moto jacket in Beverly Hills (Credit: WENN)
Ashley wore a printed maxi dress from ále by Alessandra, an ivory moto jacket from IRO, and some flat brown lace-up sandals.
Ashley Tisdale steps out in Beverly Hills wearing a tie-dye maxi dress paired with an ivory moto jacket and a leopard-print tote on April 18, 2014 (Credit: WENN)
Everything was fine until we noticed her purse—a studded leopard-print Valentino bag. While the bag itself was stylish, it clashed with the print and color of her dress.
A close-up of Ashley Tisdale’s studded leopard-print Valentino bag that clashed with her tie-dye maxi dress (Credit: WENN)
The combination didn’t work—mainly because her outfit featured texture from the cutout and lace-up details on her shoes. We’re torn between appreciating the unexpected appeal of her look and disliking the mismatched pieces.
A close-up of Ashley Tisdale’s brown lace-up sandals, adding texture to her outfit (Credit: WENN)
Well, what do you think? Yay or nay? In your opinion, did Ashley score a hit or a miss? Did she over-decorate or not?
We’re a little hesitant to give her a thumbs down here. After all, while the mix seems a little too “busy,” there are parts of her outfit that we like. Do you agree?
If we could remove one thing from her outfit, it would likely be the bag. Switching to a simpler one in solid brown or black would have made an enormous difference.
ále by Alessandra Caravan Maxi Dress in Smoke, $182
If you fancy Ashley’s look, you can easily copy it by grabbing the pieces in her ensemble. Please do us a favor; don’t use a printed tote. Go with a basic brown or black bag instead. If you want a pop of color, a tote in solid red will do, too.
ále by Alessandra Caravan Maxi Dress, $182 / IRO Ashville Leather Jacket, $1,200
Ashley’s spring-appropriate Steve Madden ‘Paiigge’ sandals feature cutout detailing throughout the faux leather uppers and lace-up closures that run up to the ankles. Here they are in dark brown, up close and personal for you:
Steve Madden “Paiigge” Lace-Up Sandals, $90
Like the look? While these exact sandals are sold out, you can find similar strappy styles at Zappos—perfect for spring’s easy, breezy vibe.
While that outfit left us feeling slightly conflicted, Ashley has had much more cohesive maxi dress moments.
Ashley Tisdale’s Airport Style: AllSaints Ikat Maxi Dress at LAX
Ending a week-long vacation in Hawaii, Ashley Tisdale was seen arriving at LAX in March 2012.
Ashley got our attention with the cute and comfy-looking ikat print maxi dress she wore for the flight. Her dress also gave us déjà vu!
At first, we thought this dress was a somewhat faded version of a dress she wore just days earlier. She styled it with Sleep Under The Star sandals from BC Footwear and authentic Ray-Ban sunglasses.
Ashley Tisdale exuded casual chic at LAX on March 23, 2012, accessorizing her AllSaints Ikat Maxi Dress with a Balenciaga Giant City bag in light blue, BC Footwear’s ‘Sleep Under the Stars’ sandals, and Ray-Ban 3025 Aviator sunglasses (Credit: Visual / WENN)
Ashley Tisdale’s dress is this ikat maxi dress from AllSaints:
AllSaints Ikat Maxi Dress, $150.00
A year earlier, Ashley showed off a more laid-back approach to airport style—and nailed it.
Boho Glam: Ashley Tisdale in Free People Maxi Dress at Cloud 9 Premiere
In December 2012, the ever-busy career woman was relishing her executive producer role in a Disney Channel original film called Cloud 9, attending the screening event with the film’s leading stars at Burbank.
Ashley Tisdale exudes boho-chic vibes in a stunning Free People maxi dress (Credit: Daniel Tanner / WENN)
The story centers around a prima donna snowboarder named Kayla, who was kicked off her team and forced to train with an injured former snowboarding champion named Will. We can only guess what tweentastic romance comes next.
Ashley Tisdale looked effortlessly chic at the Cloud 9 premiere on December 18, 2013, donning a taupe Blesse’d are the Meek San Jose maxi dress paired with a noir IRO Ashville leather jacket, accessorized with an elegant Alexa Leigh gold pave diamond Elijo ring (Credit: Daniel Tanner / WENN)
The then-28-year-old actress wore one of her boho-chic looks (it seems BFF Vanessa Hudgens’ style had completely rubbed off on her).
She chose a maxi dress from Free People, which she wore underneath a black leather jacket from Iro. Ashley also accessorized with silver necklaces and rings.
Ashley Tisdale accessorized her outfit with layered necklaces, including a distinctive key pendant and an array of charms (Credit: Daniel Tanner / WENN)
Luke Benward is 6ft 2 (188 cm) tall, significantly taller than Dove Cameron, who is 5ft 2 (157.5 cm), and Ashley Tisdale, who is 5ft 2 ½ (158.8 cm).
Ashley Tisdale, Dove Cameron, and Luke Benward pose at the Cloud 9 premiere, with Ashley in a boho maxi dress and leather jacket, Dove in a pastel heart sweater and statement fringe heels, and Luke keeping it casual in jeans, boots, and a patterned scarf (Credit: Daniel Tanner / WENN)
Her crochet maxi dress is no longer available online, but you can find similar boho-inspired styles at Nordstrom.
Ashley Tisdale looks stunning with her wavy blonde hair complemented by subtle makeup (Credit: Daniel Tanner / WENN)
We’re actually still waiting for Ashley to add a bit of variety to her style because her boho look is getting a bit old (not to mention that it never really fit her all that well from the beginning).
Ashley Tisdale stuns in a taupe maxi dress paired with a black leather jacket, accessorized with layered necklaces (Credit: Daniel Tanner / WENN)
We would love to see Ashley in more structured couture pieces since the girl has the essential red carpet qualities to make such ensembles work. Until then, let me sigh.
Free People San Jose Maxi Dress, $168
Ashley Tisdale’s Free People Two-Piece Dress: Flattering for Smaller Busts
If one cult brand can brag of a healthy celebrity following, that would be Free People.
Countless starlets have been spotted wearing Free People dresses, just one of them being Ashley Tisdale. She’s known for her flat belly and relatively small breasts.
Ashley Tisdale’s two-piece dress is perfect for flat-chested women (Credit: WENN)
The former Disney cutie wore Free People’s Emma Too Fer dress in washed coal while out and about in Beverly Hills. Check out the look she put together:
Ashley Tisdale arrived at the Andy Lecompte Salon on February 25, 2012, in a stylish ensemble featuring a Doma Cropped Moto Jacket, Lna Grey Muscle Tee, Free People Emma Too Fer Dress, accessorized with pieces like Chanel 5185 sunglasses, Steve Madden Wesscot Platform Booties, and a Chanel CC Quilted Glazed Leather Tote, complemented by various jewelry items including Dogeared bracelets, a Vanessa Mooney necklace, and Kara Ackerman hoop earrings (Credit: WENN)
What do you think? It’s not bad, right? The dress is quite feminine, but she added some edgy accessories and made them look fierce.
Here’s a closer view of Ashley’s FP dress. It’s a two-tone number with a light-colored overlay on the chest, which creates that two-piece effect while making the bust area appear fuller (perfect for flat-chested women!). The dress also comes in peach sand.
Free People Emma Too Fer Dress in Washed Coal and Peach Sand, $88
You can also steal Ashley’s look by topping the dress with this gorgeous leather jacket:
Free People Double Breasted Vegan Leather Jacket, $198
Ashley Tisdale isn’t the only petite star proving that maxi dresses can work beautifully on a smaller frame—especially when styled with the right footwear. If you’re still hesitant about the length, take a cue from these other stylish celebs who elevate their maxi looks (literally) with a great pair of heels.
How Petite Celebrities Style Maxi Dresses With Heels
Here are some petite celebrities who have masterfully combined maxi dresses with heels to create elegant and elongated silhouettes:
Nicole Richie’s Bohemian Maxi Look
- Event: Fashion’s Night Out
- Outfit: Nicole Richie (5’1″) donned a Winter Kate silk maxi dress, showcasing her bohemian style.
- Footwear: She paired the dress with high-heeled sandals, adding height and complementing the flowing silhouette.
- More Details: Nicole Richie’s Fashion’s Night Out ensemble
Vanessa Hudgens’ Effortless Maxi Style
- Event: Coachella Music Festival
- Outfit: Vanessa Hudgens (5’1″) embraced a printed maxi dress, reflecting her signature boho-chic aesthetic.
- Footwear: She elevated the look with wedge heels, enhancing her height while maintaining comfort.
- More Details: Vanessa Hudgens’ Coachella fashion highlights
Rachel Bilson’s Casual Maxi Ensemble
- Event: Errands in North Hollywood
- Outfit: Rachel Bilson (5’1″) opted for a red maxi skirt paired with a black top, achieving a relaxed yet stylish look.
- Footwear: She completed the outfit with flat sandals, demonstrating that petites can wear maxi lengths with the right proportions.
- More Details: Rachel Bilson’s approach to maxi skirts and footwear
Selma Blair’s Vibrant Maxi Shirt Dress
- Event: Outing on Melrose Avenue
- Outfit: Selma Blair (5’2½″) was spotted in a bold orange maxi shirt dress with a tie-dye pattern.
- Footwear: She paired the dress with flat sandals, keeping the look casual and comfortable.
- More Details: Selma Blair’s eye-catching maxi dress moment
These examples illustrate that with thoughtful styling, petite individuals can confidently wear maxi dresses. Pairing them with heels or choosing the right accessories can create a balanced and elongated silhouette.