From PEOPLE Magazine Click to enlarge
Change is never easy, but Janet Jackson sure makes it look that way. With a new album (20 Y.O., out Sept. 26) and a new body—she shed some 60 lbs. in a little over six months—the 40-year-old superstar has now enlisted the help of stylist Kim Bowen and is working on a new look. "I was always a tomboy growing up, and I still have that in me," she says. "But my style has become a lot softer, a lot more womanly." Here, she comments on some of the highlights—and lowlights—of her journey from there to femininity.

2006
"To me, it's about being able to take bits and pieces and put them together to create your own style"

1970
"My mother used to dress me for school in a skirt, and I would run back in the house to put on pants"

1975
"Oh my God! This makes me laugh. I was about 8 years old, and I was trying to look like Mae West. Look at those cheeks"

1990
"I still have this Rhythm Nation outfit. The key thing started when I was a kid. My brother Mike and I took care of all our animals. I kept the cage key on my earring"

2001
"It's Versace, and the first time I wore a short dress. [Stylist] Andrea Lieberman talked me into it. I was apprehensive—it's see-through. I checked myself out from every angle"

2002
"Those used to be my favorite jeans, and the coat was a friend's. I just threw them on for an Oscar party. Not the outfit for a function like that. I just wasn't into going out"

2004
"This is completely wrong. The tank shouldn't be with the shirt or the shirt with those Libertine pants. I was on tour—it's one of those so-tired-you-don't-care moments"

2005
"There's just too much going on here! I absolutely love this jacket, but I should have worn it with a pair of long, maybe big-leg, pants with really high heels. Minus the skirt"

2005
"Gaining weight was really uncomfortable for me. It was hard to find something to wear. I think Wayne [Lucas, the stylist] did a nice job. I love the jacket. The skirt is vintage"

2006
"When I saw this Bill Blass dress, I thought, 'Oh my God, I want it.' It was the beginning of me really embracing my femininity, my womanhood"