Rapper Big Sean first made a splash in 2007, when Kanye West signed him to G.O.O.D Music, but he's always been somewhat of an underdog in the music industry. Now, the 28-year-old Detroit-native is making a self-induced comeback—or a "bounce back," as he puts it—with his newest album, "I Decided." The album, which dropped February 3rd, has some critics (and Jay Z) calling him "Most Improved." In other words, Big Sean's recent transformation is the musical equivalent of a Werewolf Bar Mitzvah—that he's throwing for himself.

If that wasn't clear, the phrase: "The underdog just turned into the wolf," is embroidered on the backs of Big Sean's "I Decided" merch, which he released at pop ups in New York, Los Angeles, Detroit, and Toronto this past weekend. The collection as a whole is an ode to re-invention, with other catchphrases like, "No favors," and "Nothing changes if nothing changes" printed in a circle. It's a testament to fashion's power to project the person you want to be, and that thanks to the newfound merch craze, we can wear confidence on our sleeves.

Big Sean is no stranger to fashion--he wore a pink Gucci jacket in his music video for the song "Moves," and was spotted in a Maison Margiela silk shirt backstage at his recent Saturday Night Live performance. On Friday night at the opening of his New York pop up, he flaunted an accessory that money can't buy: a diamond-encrusted Rock-A-Fella chain that Jay Z gave him after "I Decided" dropped, saying he "earned it."

Overall, Big Sean's look declares that he's not shy about being simultaneously confident and vulnerable. And the merch accompanying "I Decided" is precisely a reflection of that, with bold statements flanked by delicate roses. Below, Big Sean opens up about how he translates his current mood to his clothes.

Thomas Falcone

Your new album, "I Decided," and its merch are all about the underdog coming up. How do you dress confidently?
It’s all about how you feel. When you put an outfit on and you feel like you’re 100-percent ready to go—that’s it. Whether it’s taking a risk or doing something that’s been done before, you have to feel good about it. That’s when it’s right.

Does fashion help make you feel confident?
Yeah, I like looking good! When you look your best, you feel your best. And I’m not saying that in a shallow way or anything, I’m saying it in a real way. Like, when I get my haircut, I’m feeling good.

Who are some of the best dressed people, in your opinion, living or dead?
I think Biggie and 'Pac were two of the best dressed rappers; Kanye; Pharrell is the god; and Jay Z.

There are a lot of roses on your clothing. Do you have any advice for what guys should get girls on Valentine's Day?
Roses are definitely a way to go, but maybe try to get creative with it, too. I give really good gifts, I don't want to go into it though. A gift doesn't have to cost a lot of money; something that's thoughtful goes a lot farther than something that's worth a lot. Sometimes. [Laughs.]

Thomas Falcone

Do you have a prized possession in your closet?
I like jewelry a lot. I have a ring with a green emerald that is my favorite. Jason of Beverly Hills did it. I haven't seen one as good as this, which is why I had to get it. I also have a camouflage chain. It's a Cuban, but it's got a different twist. It's really well done.

Is there anything you would never wear?
Nah, I like to take risks. I'll wear anything, as long as I don't look ridiculous.

What about grooming? Do you do anything to treat yourself?
I need to start getting more massages and manicures.

What's the most fire piece you saw recently, that you need to have?
I really like Gucci lately. I know that's cliché at this point to say, but they've really been killing it. I love their shoes.

You have the furry loafers. Do you wear them in the winter without socks?
Yeah I like those. They're comfortable. But I don't wear them in the winter. I've been trying to do less fur now. I've been seeing a lot of stuff about how they get the fur and I'm trying to be more conscious.

Thomas Falcone

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