Pulling off high-glam fashion is one thing—but making a fun or edgy look work on the red carpet? That’s a whole different challenge.
While most red carpet events call for polished gowns and classic glamour, festivals like the iHeartRadio Music Festival give stars the freedom to showcase their bolder, more unconventional style choices. But as we’ve seen time and again, pushing fashion boundaries doesn’t always lead to style wins.
Here are a few celebs who took a risk with edgy looks at the iHeartRadio Music Festival… but didn’t quite stick the landing.
1. Hilary Duff’s Leather Look Falls Flat in Anthony Vaccarello Mini Dress
Hilary Duff wore a sexy leather mini dress by Anthony Vaccarello that accentuated her cleavage and toned physique. While we love how this hot momma takes care of her figure, we’re not big fans of her dress.
Hilary Duff elongated her silhouette with sleek black Christian Louboutin “So Kate” pumps, which added height and balanced the bold details of her sculptural leather mini dress
The leather works very well, and the cutout is hot, but the ruffled metallic detail on the side is really distracting.
Best known for her role as Lizzie McGuire, she styled the dress with elongating “So Kate” red sole pumps by Christian Louboutin and accessorized with Alexis Bittar bangles and Renee Sheppard Deco diamond drop earrings.
Hilary Duff’s Signature Style: A Love Affair With Louboutin Heels
Hilary Duff has consistently showcased her affinity for Christian Louboutin heels, seamlessly incorporating them into her chic ensembles. A notable instance was her 25th birthday celebration, where she elevated her look with vibrant red ‘Bianca’ pumps, adding a bold splash of color to her outfit.
During the Broadway opening night of ‘The Elephant Man,’ Hilary exuded sophistication by pairing a camel coat with black suede ‘So Kate’ pumps, further cementing her status as a Louboutin devotee. Her enduring love for these iconic red-soled heels underscores her impeccable taste and fashion-forward sensibility.
Hilary Duff flashes underboob at the iHeartRadio Music Festival 2014 (day 2) held at the MGM Grand Garden Arena in Las Vegas on September 21, 2014 (Credit: WENN / Judy Eddy / DJDM)
2. Iggy Azalea Misses the Mark in ’80s-Inspired Figure Skater Outfit
Iggy Azalea ignited the stage with her performance at the event, but she fell short with her outfit on the arrivals’ red carpet. Wearing a multicolored dress with side slits that displayed her underwear, Iggy looked like a pop star from the ’80s era.
Iggy Azalea paired her bold, ’80s-inspired patchwork mini dress with black platform ankle boots that grounded the look and added height—though the heavy footwear slightly clashed with the playful vibe of her outfit
The combination of studs, sequins, and a belt overwhelmed the look, veering into visual clutter.
Iggy Azalea looked like a figure skater at the iHeartRadio Music Festival 2014 (day 2) held at the MGM Grand Garden Arena in Las Vegas on September 21, 2014 (Credit: WENN / Judy Eddy / DJDM)
3. Sophia Bush’s Sheer Lace Monique Lhuillier Dress Sparks Mixed Reactions
We love Sophia Bush, and there’s no denying that she looked glowing with her honey hair and skin. However, the dress choice was a failure.
Sophia Bush complemented her sheer lace Monique Lhuillier dress with nude Christian Louboutin “Iriza” pumps, which visually elongated her legs and kept the focus on the intricate mesh detailing
Sophia chose to wear a see-through Monique Lhuillier mesh dress, revealing a nude-colored undergarment.
Chad Michael Murray’s ex-wife has a great figure, though we prefer seeing it styled with more refined sophistication. She accessorized with a Rauwolf Octagon clutch and slipped into Christian Louboutin’s “Iriza” half-d’Orsay pumps in nude patent leather—an ever-popular choice for their leg-lengthening illusion and timeless versatility.
The American actress also flaunted her legs in an H&M Conscious beige high-neck sheer dress and nude patent Christian Louboutin Pigalle pumps at H&M’s Conscious Collection Dinner.
Sophia Bush’s Enduring Affection for Christian Louboutin Heels
Sophia Bush has long demonstrated her penchant for Christian Louboutin footwear, seamlessly incorporating the brand’s signature styles into her ensembles.
Another standout moment was at the 2015 season four premiere of Girls when she donned a plunging Lela Rose dress complemented by striking Bille et Boule pumps featuring studded PVC and suede—a testament to her edgy yet sophisticated fashion sense.
Sophia Bush shows off her nude underwear at the iHeartRadio Music Festival 2014 (day 2) held at the MGM Grand Garden Arena in Las Vegas on September 21, 2014 (Credit: WENN / Judy Eddy / DJDM)
4. Taryn Manning’s Yellow Lace Disaster With Sequined Shrug Misfires on the Carpet
Orange Is the New Black star Taryn Manning may just be the worst dressed of the night. The petite celebrity wore a floor-length lace dress in bright yellow and paired it with an ill-fitting sequined shrug.
Taryn Manning’s floor-length yellow lace gown may have overwhelmed her petite frame, but her pointed-toe heels subtly peeked through to add a touch of elevation and polish to the bold ensemble
If you’re on the shorter or petite side and want to rock a maxi dress without feeling overwhelmed by the fabric, check out our guide on how to wear a maxi dress when you’re short. It’s filled with practical styling tips and inspiration to help you pull off the look with confidence.
She completed the look with tousled hair and moody, dark lipstick, which unfortunately added to the ensemble’s overall discord.
Taryn Manning poses in a yellow lace dress with a sequined shrug at the iHeartRadio Music Festival (Credit: WENN / Judy Eddy / DJDM)
While not every outfit hit the right note, others stood out for all the right reasons—especially when it came to footwear. From edgy lace-up heels to crystal-studded pumps, these iHeartRadio Music Festival shoe moments prove that great style often starts from the ground up.
Stepping Out in Style: Shoe Highlights from the iHeartRadio Music Festival
The iHeartRadio Music Festival has always been a hotspot for celebrities to showcase their unique fashion sensibilities. Here are some standout shoe moments from the festival:
Dua Lipa’s Archival Gucci Lace-Up Sandals
- Event: 2024 iHeartRadio Music Festival
- Outfit: Dua Lipa captivated audiences in a silk waistcoat vest from Ann Demeulemeester’s Spring 2006 collection, paired with a floor-length satin maxi skirt featuring a thigh-high slit.
- Footwear: She completed her ensemble with archival lace-up sandals designed by Tom Ford for Gucci’s Fall/Winter 2002 collection, adding a touch of vintage elegance to her look.
- More Details: Dua Lipa’s Archival Fashion Statement at iHeartRadio Music Festival 2024
Lucy Hale’s Saint Laurent ‘Kiki’ Crystal-Embellished Sandals
- Event: 2019 iHeartRadio Music Festival
- Outfit: Lucy Hale turned heads in high-rise leather shorts from Saint Laurent, styled with a pagoda-shoulder jacket and a metallic striped blouse.
- Footwear: She showcased her legs with Saint Laurent’s ‘Kiki’ crystal-embellished satin sandals, adding a touch of sparkle to her edgy ensemble.
- More Details: Lucy Hale’s Stunning Appearance at the 2019 iHeartRadio Music Festival
Katy Perry’s Versace Snakelike Button Calf Sandals
- Event: 2013 iHeartRadio Music Festival
- Outfit: Katy Perry embraced a jungle-themed look with a rose-printed neoprene dress from Faith Connexion, complemented by an animal silhouette neck cuff and braided hairstyle.
- Footwear: She completed her ensemble with Versace’s snakelike button-calf sandals from the Spring/Summer 2011 collection, which added an edgy flair to her performance attire.
- More Details: Katy Perry’s Jungle-Themed Outfit at iHeartRadio Music Festival
Miley Cyrus’ Christian Louboutin ‘Chiara’ Embellished Suede Pumps
- Event: 2020 iHeartRadio Music Festival
- Outfit: Miley Cyrus delivered a show-stopping performance in a sheer black catsuit by Thierry Mugler, featuring strategically placed black panels.
- Footwear: She elevated her daring look with Christian Louboutin’s ‘Chiara’ embellished suede pumps, known for their light-catching crystal details and mesh panels.
- More Details: Miley Cyrus’ Nearly Naked Performance Covering Blondie’s ‘Heart of Glass’
Kylie Jenner’s Aquazzura ‘Amazon’ Lace-Up Sandals
- Event: 2013 iHeartRadio Music Festival
- Outfit: Kylie Jenner showcased an edgy leather dress, embodying a fierce street-chic aesthetic alongside her sisters.
- Footwear: She accentuated her look with Aquazzura’s ‘Amazon’ lace-up sandals, featuring intricate lacing and a stiletto heel, adding a bold touch to her ensemble.
- More Details: Kardashian-Jenner Sisters’ Edgy Fashion at iHeartRadio Music Festival
These moments highlight the diverse and stylish footwear choices that have graced the iHeartRadio Music Festival over the years, reflecting each artist’s unique fashion sense.