Photo: Jessica Simpson/InstagramJessica Simpsonjust proved some looks never go out of style.The multi-hyphenate mogul, 41, shareda photoof herself wearing a 19-year-old black Gucci pencil skirt on Instagram Friday. She completed the look with a cropped blazer, white tank top, platform sandals and oversize sunglasses.“Fun fact — I wore this Gucci skirt promoting the first season of Newlyweds at 22yrs old on Craig Killburn (@rachelzoeremember this?)#19YearsLater#HOARDER#CANCERIAN,” the singer and fashion industry star, captioned the outfit pic on instagram.Stylist Rachel Zoe responded in the comment section, writing, “😂😂😂😂😂 OMG YES!!!“Back in 2002, Simpson styled the pencil skirt with a tight, black sleeveless turtleneck and coordinating black sling-back pumps. She wore her hair styled in a side-swept, curled Marilyn Monore-styled bob.In April, Simpson — who shares childrenMaxwell Drew, 10, Ace Knute, 8, and Birdie Mae, 3, with husband Eric Johnson — opened up to PEOPLE aboutrespecting her bodyno matter how her weight fluctuated.“I always celebrate my body,” she said. “The fact that it made children is unreal, … but you just don’t ever think you’re going to fit back into things. It’s crazy. A woman’s body is phenomenal in what it can do.“Adding that she has “been happy at every size,” with the exception of her weight “at the end” of her pregnancies, Simpson says, “I’ve definitely embraced myself.““And I think that people get that with me, and they know that I’m being open and that I’m being honest about my life.“Never miss a story — sign up forPEOPLE’s free daily newsletterto stay up-to-date on the best of what PEOPLE has to offer, from juicy celebrity news to compelling human interest stories.Earlier that month, the “With You” singer sharedan empowering messageabout being comfortable in her own skin while on a beach vacation with her family in Cabo San Lucas.“I have gained and lost 100lbs 3x so I never thought this moment could or would happen,” shewrotealongside the sultry snap, adding, “but I’m finally spring breakin' wearin' a BIKINI!!!!!!“jessicasimpson/InstagramSimpson told PEOPLE that the experience was a reminder to have confidence in herself.“I never thought of being in a bikini again, because I was stretched out as big as the couch,” she said. “So to be able to put on a bikini … I just hadn’t thought that was even a goal until I put it on, and I was like, ‘I think I was afraid of that.’ ““And for me, as a woman, to be able to look as good as I feel was a major moment,” she added. “You’re proud of yourself and you deserve it … [and you’re] understanding yourself and feeling good on the outside. When those two things click, the sky’s the limit.”

Photo: Jessica Simpson/Instagram

Jessica Simpson/Instagram

Jessica Simpsonjust proved some looks never go out of style.The multi-hyphenate mogul, 41, shareda photoof herself wearing a 19-year-old black Gucci pencil skirt on Instagram Friday. She completed the look with a cropped blazer, white tank top, platform sandals and oversize sunglasses.“Fun fact — I wore this Gucci skirt promoting the first season of Newlyweds at 22yrs old on Craig Killburn (@rachelzoeremember this?)#19YearsLater#HOARDER#CANCERIAN,” the singer and fashion industry star, captioned the outfit pic on instagram.Stylist Rachel Zoe responded in the comment section, writing, “😂😂😂😂😂 OMG YES!!!“Back in 2002, Simpson styled the pencil skirt with a tight, black sleeveless turtleneck and coordinating black sling-back pumps. She wore her hair styled in a side-swept, curled Marilyn Monore-styled bob.In April, Simpson — who shares childrenMaxwell Drew, 10, Ace Knute, 8, and Birdie Mae, 3, with husband Eric Johnson — opened up to PEOPLE aboutrespecting her bodyno matter how her weight fluctuated.“I always celebrate my body,” she said. “The fact that it made children is unreal, … but you just don’t ever think you’re going to fit back into things. It’s crazy. A woman’s body is phenomenal in what it can do.“Adding that she has “been happy at every size,” with the exception of her weight “at the end” of her pregnancies, Simpson says, “I’ve definitely embraced myself.““And I think that people get that with me, and they know that I’m being open and that I’m being honest about my life.“Never miss a story — sign up forPEOPLE’s free daily newsletterto stay up-to-date on the best of what PEOPLE has to offer, from juicy celebrity news to compelling human interest stories.Earlier that month, the “With You” singer sharedan empowering messageabout being comfortable in her own skin while on a beach vacation with her family in Cabo San Lucas.“I have gained and lost 100lbs 3x so I never thought this moment could or would happen,” shewrotealongside the sultry snap, adding, “but I’m finally spring breakin' wearin' a BIKINI!!!!!!“jessicasimpson/InstagramSimpson told PEOPLE that the experience was a reminder to have confidence in herself.“I never thought of being in a bikini again, because I was stretched out as big as the couch,” she said. “So to be able to put on a bikini … I just hadn’t thought that was even a goal until I put it on, and I was like, ‘I think I was afraid of that.’ ““And for me, as a woman, to be able to look as good as I feel was a major moment,” she added. “You’re proud of yourself and you deserve it … [and you’re] understanding yourself and feeling good on the outside. When those two things click, the sky’s the limit.”

Jessica Simpsonjust proved some looks never go out of style.

The multi-hyphenate mogul, 41, shareda photoof herself wearing a 19-year-old black Gucci pencil skirt on Instagram Friday. She completed the look with a cropped blazer, white tank top, platform sandals and oversize sunglasses.

“Fun fact — I wore this Gucci skirt promoting the first season of Newlyweds at 22yrs old on Craig Killburn (@rachelzoeremember this?)#19YearsLater#HOARDER#CANCERIAN,” the singer and fashion industry star, captioned the outfit pic on instagram.

Stylist Rachel Zoe responded in the comment section, writing, “😂😂😂😂😂 OMG YES!!!”

Back in 2002, Simpson styled the pencil skirt with a tight, black sleeveless turtleneck and coordinating black sling-back pumps. She wore her hair styled in a side-swept, curled Marilyn Monore-styled bob.

In April, Simpson — who shares childrenMaxwell Drew, 10, Ace Knute, 8, and Birdie Mae, 3, with husband Eric Johnson — opened up to PEOPLE aboutrespecting her bodyno matter how her weight fluctuated.

“I always celebrate my body,” she said. “The fact that it made children is unreal, … but you just don’t ever think you’re going to fit back into things. It’s crazy. A woman’s body is phenomenal in what it can do.”

Adding that she has “been happy at every size,” with the exception of her weight “at the end” of her pregnancies, Simpson says, “I’ve definitely embraced myself.”

“And I think that people get that with me, and they know that I’m being open and that I’m being honest about my life.”

Never miss a story — sign up forPEOPLE’s free daily newsletterto stay up-to-date on the best of what PEOPLE has to offer, from juicy celebrity news to compelling human interest stories.

Earlier that month, the “With You” singer sharedan empowering messageabout being comfortable in her own skin while on a beach vacation with her family in Cabo San Lucas.

“I have gained and lost 100lbs 3x so I never thought this moment could or would happen,” shewrotealongside the sultry snap, adding, “but I’m finally spring breakin' wearin' a BIKINI!!!!!!”

jessicasimpson/Instagram

jessica simpson

Simpson told PEOPLE that the experience was a reminder to have confidence in herself.

“I never thought of being in a bikini again, because I was stretched out as big as the couch,” she said. “So to be able to put on a bikini … I just hadn’t thought that was even a goal until I put it on, and I was like, ‘I think I was afraid of that.’ "

“And for me, as a woman, to be able to look as good as I feel was a major moment,” she added. “You’re proud of yourself and you deserve it … [and you’re] understanding yourself and feeling good on the outside. When those two things click, the sky’s the limit.”

source: people.com