Joshua Goldman
Joshua Goldman
min read · July 24, 2025 · Entertainment

Jessica Simpson's Bold Night Out: Overcoming a Live TV Malfunction with Style

Jessica Simpson, 45, brushed aside an embarrassing wardrobe malfunction as she enjoyed a night out in New York City on Wednesday

JESSICA SIMPSON SHINES BRIGHT AFTER WARDROBE MALFUNCTION, JOKES ABOUT FLASHING FANS ON TODAY SHOW!

The queen of sass, Jessica Simpson, brushed off an embarrassing wardrobe malfunction like a pro and flashed her signature charm on the Today show just hours after the mishap. The 45-year-old TV personality, mom-of-three, and pop sensation was spotted looking radiant in a leggy orange minidress with shimmering sun patterns as she enjoyed a night out at The Hotel Chelsea in New York City.

But let's get to the juiciest part - Jessica's wardrobe malfunction on Today earlier that day! The corset-style dress, which normally covers her bust, struggled to stay put, flashing her pink bra to millions of viewers. And guess what? Jessica took it all in stride, singing through the mishap like a pro and even cracking a joke about it with host Jenna Bush Hager.

The TV personality had taken to the stage on the Today show hours earlier where she suffered a mishap with her outfit mid-performance as it was being broadcast live

"I had a malfunction here, and everywhere... but it's okay! I think my boob stayed in, so that's good!" she quipped, flashing her signature wit. And if that wasn't enough, Jessica also took a swipe at her dating history during the interview, sharing her non-negotiables for her next partner.

"My type of person is one-of-a-kind... I don't have like, a look or anything like that. I just like someone to be individually who they are and exude confidence without the ego," she gushed, seemingly taking aim at her rocky relationship with first husband Nick Lachey. The performer also emphasized that whoever she dates next has to be "a very good kisser" - and we're guessing there are plenty of takers out there!

In a press release, per thescholarlynote.com, Jessica explained the inspiration behind her new single Fade: "This song came straight from my heart. I had just lived through this heavy, emotional moment, but there was no way I was gonna cancel my songwriting session. I walked into the studio with tears still on my cheeks, and what came out was a prayer."

The mom-of-three put on a leggy display in an eye-catching minidress as she grabbed dinner

Fade is a track that will be found on her upcoming album Nashville Canyon, Part 2 - set to drop on September 4. The performer previously dropped her EP Nashville Canyon, Part 1 back in March.

So, it seems like Jessica Simpson is not only rocking the stage but also slaying the dating game (or at least, that's what she wants you to think!) Stay tuned for more updates on this pop sensation's latest endeavors - and maybe even a few juicy rumors!

Simpson donned a sparkling orange ensemble that had a shimmering sun pattern on the right side

Jessica's blonde locks were parted to the side for her fun night out

The singer accessorized the nighttime look with a pair of glittering hooped earrings

A warm blush was added onto her cheekbones for a radiant glow while a glossy, nude-colored tint was worn on her lips for a finishing touch

Jessica was seen at The Hotel Chelsea for her night out and stopped to greet awaiting fans outside the building

However, Simpson had a wardrobe malfunction when her taupe dress slipped down her cleavage - showing off her pink bra

Video of the performance shows Jessica singing through the wardrobe mishap, either unaware of or not minding that accidental bra flash

But the newly-single star didn't let the embarrassing mishap ruin her day as she even cracked a joke about it with the Today show correspondents

'How does it feel back on the stage, the first release in 15 years?' NBC News journalist Peter Alexander asked Simpson

The wardrobe mishap wasn't Jessica's only head-turning moment during her Today appearance

Simpson also took a swipe at her dating history while sharing her list of relationship non-negotiables during an interview with host Jenna Bush Hager

'My type of person is a one-of-a-kind,' she gushed. 'I don't have like, a look or anything like that. I just like for somebody to be individually who they are and exude confidence without the ego'

On Tuesday, the singer seemingly made a thinly-veiled dig at her ex Eric Johnson when she dropped her new single Fade; former couple seen in 2023 in L.A.

She added that the single, 'is about watching someone you love slip away in real time, while trying to hold on to something that's already gone'; seen in May