She was just 16 years old when she took the country music world by storm and now, a mere six years later, taylor swift is nothing short of a crossover superstar with a rapid breaking collection of... See More
She was just 16 years old when she took the country music world by storm and now, a mere six years later, taylor swift is nothing short of a crossover superstar with a rapid breaking collection of hits and millions of loyal fans. And now, she's gracing her third cover of "glamour" magazine. They invited me behind the scenes for an exclusive interview and to write their no-fly cover story. It was 100-plus degrees in nashville when we sat down to talk about money, fame, her new album and of course, love. ♪ Reporter: She's music's golden girl, selling arenas out in minutes and driving some fans to near his tiria. But you'd never know it on a blistering august day in nashville. Hey. Reporter: Taylor swift, show biz's wealthiest 20-something. Arrives on time, entourage-free. Look at all these things. Ooh. Amazing. Reporter: Here to shoot her third cover story for "glamour," newstands, october 9. The set is an old train station and taylor is all aboard. Photographer ellen, and "glamour's" creative team shoot her in outfit after outfit, each ensemble vying for the all-important cover shot. When did you decide you wanted taylor swift? We pretty much decided we wanted her the month after we had on our cover last time. Reporter: Ban bach in "glamour" the editor in chief knows cover gold when she sees it. This is her first "glamour" cover. August 2009. This is taylor number two. Reporter: She's growing up. What will it be this time? I used to be particular about things and now I'm just, I walk in and I'm like, whatever you want do. Just put clothes on me, I don't care. Reporter: For a young mogul swift as the rarecombination of letting things roll off her back with wide-eyed enthusiasm. You fight your battles. Reporter: It may look like a yard sale, racks and tables but all vintage and designer duds selected with swift in mind. I'm super tall. Reporter: You are tall. Tall. No heels. But you have on kitty shoes. This is my favorite thing. I love this. Reporter: The real taylor swift would use these. I for real will steal them. Reporter: I think you should. And kind of act like didn't know I was doing it. Reporter: Try it. Make a getaway. Sort of like, I just need a bag to hold my sandwich. Just needed to take my lunch home. Reporter: In person she's playful and even a little goofy. She's taken a bit of a rousing for her aw shucks enthusiasm. It was spoofd by blake shelton at this year's academy of country music wards. Taylor will have her own perfume it's call ed -- I can't believe I smell this good! Now. Now taylor swift is here. Reporter: Even by kristen wiig on "saturday night live." So that look that you give, that "i won" look. People make so nuchb of me for that. I don't know. It's like if you win an ward isn't that crazy? Isn't that crazy? How do you sit there and be like, oh. Another grammy. I guess I'll go get that now. Reporter: So, you were not blase? I try to be something but it's just hard when you get excited about stuff. Reporter: Many speculated about her latest enthusiasm. So, as you know, there is a lot of talk about you in the kennedys these days. Is there? Reporter: There is. Do tell. Reporter: Reports that you're dating conor kennedy, true? I don't talk about my personal life in that great detail. I write by the all in my songs but when I get in an interview it's just sort of feels -- it's not as much what I do. Talking about it. Reporter: Conor, son of robert kennedy, jr., Is an 18-year-old student. Eth el kennedy was asked what she would think of having as a granddaughter-in-law and she said, we should be so lucky. She's fantastic. I love her. I met her about a year ago and she just, she puts you at ease when you're around her and she's just the embodiment of youthful energy. It's really inspiring. Reporter: Speaking of inspiration, taylor's new album "red" released october 22, is inspired by a familiar theme. Love. She's already released one track, a take on love gone wrong "we are never ever getting back together." ♪ We are never ever ever getting back together ♪ Reporter: It shot to number one on I tunes in 32 countries. Setting records along the way. This morning on "gma" she debuted another song. The song we're releasing this week is the title track "red." ♪ Reporter: You're the number one earning star 30 years old or younger, beating justin bieber, lady gaga, all of them. Reportedly $56 million last year. That's a lot. Reporter: Does it feel a little intimidating sometimes or not? What part of it? Reporter: It's big. It just doesn't feel that -- it doesn't feel like a weight. There are times when it gets really busy and I get intimidated by all of it but most of the time I'm able to really go back to that place where it feels balanced. Reporter: Are you a worrier? Yes. I worry about like everything. Like, like, everything. Future, past, present, where is this all going? What am guying to feel like in 20 years, what about in 28 years? What's my like going to be like? Where am guying to live? Where am guying to send my kids to school and that and that and that, literally everything. Reporter: Back in the "glamour" shoot, even taylor can't find much to worry about. Oh, my gosh, I love that! You killed it. That's so amazing. Reporter: Taylor thinks she knows what dress will make the cover. The pink one. Will she be right?
This transcript has been automatically generated and may not be 100% accurate.