Trey Songz

Songz keeps it cool and casual while promoting Rocawear at Macy's Herald Square in New York City. Photo: Astrid Stawiarz/Getty Images

Trey Songz no longer has to sing "I Gotta Make It," as the 25-year-old has come full circle with his music and style since bursting onto the scene five years ago with cornrows, white ribbed tank tops, and a piercing falsetto.

The "Bottoms Up" singer recently inked a major endorsement deal to become the new face of urban apparel brand Rocawear.

StyleList was on the scene at Macy's Herald Square in New York City as the R&B crooner descended upon a bevy of screaming fans -- mostly Trey's Angels -- to promote the new line and autograph his latest album, "Passion, Pain & Pleasure."

Dressed in a burnt orange sweater, plaid button-down shirt, distressed denim, and chocolate brown military boots, the 25-year-old proved he's worthy of the spokesperson title by wearing the perfect fall ensemble.

StyleList: What about you embodies the Rocawear brand and its future?
Trey Songz:
Rocawear is the number one urban brand right now and a lot of people didn't know that it's been the number one urban brand for the last 10 years. It went from no promotion to oversize jackets on album covers to a big "R" with a flame to this discreet "R." It's growing, and I think of myself in that way. You've watched me mature from a young man to a man with the songs I sing to the clothes I wear to the imagery and the way I'm perceived.

SL: What was your first Rocawear item?
TS: I had a whole bunch of Rocawear! There was an old rugged warehouse not too far from where I lived, and my homeboy worked there so we got the discount. I had all the big T-shirts with the "R" and the sweats. My favorite Ro\cawear item was this gray sweat suit and it had blue piping and said "Rocawear" right here [points to leg]. I probably wore it thirtysomething times [laughs].

SL: What are some of your favorites from the Fall 2010 collection?
The jeans. I love the different washes. The quality is much like a high-end denim like PRPS or Ralph Lauren. And you wouldn't really expect that from an urban line. That's what's so dope with aligning with them at this point, because they're changing and it's much like my career.

SL: Describe the Spring 2011 men's collection. Can you give us a preview of the ad campaign?
TS: It's a continuation of the fall line as far as the evolution of the brand and the growth. They got these shorts that I love... I think the fabric is chambray. It's very light, nice colors, and great T-shirts. I'm very big on simplicity, but making it look very complex. For the fall, the mood and story line was about my life and the work aspect and how lush it is. The spring campaign will be more about the fruits and luxury of it.

Check out the "Roc4Life" video below as Songz takes us through his Rocawear journey.

In other celebrity ad campaign news, check out Heidi Klum's photo shoot with Ann Taylor.