At this point, if you’re not quick to trust the almighty Hugh Hefner’s judgment, you’re taste in beautiful women must hover somewhere above photos of either Janet Reno or Whoopi Goldberg (No offense, though—Sister Act is the shit!). Month upon month, the Playboy mastermind anoints one lucky knockout as the magazine’s “Playmate of the Month,” and, every year, one of the hot-twelve earns Hef’s highest honor, that of “Playmate of the Year.” And this year, he’s outdone himself yet again.

Early last month, the coolest man alive bestowed Claire Sinclair, the October 2010 issue’s “Playmate of the Month,” as his 2011 Playmate of the Year. Having just turned 20 years old last week, the buxom Los Angeles native is one of the youngest women to ever hold the title; so young, in fact, that the Las Vegas club promoters that hosted her coronation ceremony had to shuffle her out of the venue immediately after her acceptance speech, due to the rampant alcohol on the premises. See, not all girls have it that inside nightclubs.

Sinclair isn’t your typical Playmate of the Year, though. Aside from her uniquely pre-21 age, she’s a throwback to the old 1950s pin-up days of Bettie Page, whom Sinclair has idolized since she was a little girl; a time when sexy ladies posed in vintage lingerie for the sake of thumbtacks stuck into guys’ bedroom walls. In fact, Hefner has cited Sinclair’s nostalgically sexy look as the reason why he selected her as Playboy’s latest 365-day queen.

With her run as 2011’s Playmate of the Year officially underway, Sinclair came down from her well-deserved high to chat with Complex about just what the title entails, how being under-21 has spoiled some of the fun, her days as a costumed princess, and why immaturity in men really turns her on.

Complex: How crazy has your life been since Hugh Hefner made the formal announcement about your being 2011’s Playmate Of The Year last month?

Claire Sinclair: It’s been a really hectic, but great, month. I actually don’t mind being so hectic; I’d rather be busy then sitting around at home all day, you know? But, really, it’s more a sense of relief now. Like, “Finally, they’ve announced it!” It felt like I’d been waiting forever for them to make the formal announcement and for it to be official. So, I’m really glad that I lasted through all of the anxiety. [Laughs.]

claire-sinclair-hugh-hefnerHow long did you know about it before the actual announcement?

Claire Sinclair: A couple of months. Hef actually told me during a party at the [Playboy] mansion. I had to keep it secret, because the official announcement had been set for May, and it was just killing me. I kept thinking that everything could change, and they could take it away from me before anyone else even knew I’d won the title.

I was freaking out, because I’m one of the youngest Playmates of the Years ever, and I thought that they were going to change their mind. I’m too young, I can’t promote liquor—they’re going to take it away from me. So I was freaking out until the actual day of the ceremony, and it’d become official. Then, I finally breathed. I just thought, “Cool! I’m officially Playmate of the Year now—they can’t take it away.”

Did you or Hugh Hefner talk about the concerns with your age? Because I’d imagine that you technically won’t be able to attend some of the functions or handle some of the responsibilities that might involve things like alcohol or 21-and-over club entrances.

Claire Sinclair: Well, when he told me the news, I definitely didn’t want to bring my age to his attention. He knew I was really young, of course, but I didn’t want to be like, “OK, so are you sure you want this? I’m under 21, after all.” [Laughs.] He probably thought about it, and I wasn’t going to rub that in his face. I was just happy that, regardless of him knowing my age, he picked me.

The bad thing about it, though, is that since I’m under 21—and I think this is really silly—I couldn’t be on the cover of my issue. I shot the cover of my October issue originally when I was just a Playmate, the college issue, but it got rejected because I was under 21. When you’re on the cover of Playboy, you’re kind of promoting everything inside of it, so all of the liquor advertisers pull out if there’s someone under 21 on the cover. So both times that I shot the cover, I lost it. So, that was a little depressing. [Laughs.]

So you can’t get a Playboy cover until next year, then.

Claire Sinclair: Yeah, hopefully. I’m going to ask Hef, “Hey, for my birthday, can I be on the cover of Playboy?” [Laughs.] I think that’d be a really nice birthday present. They took it away twice, so the third time’s a charm, right? We can do a big cover with me holding a bunch of balloons, or blowing out 21 candles on a birthday cake. I think that’d be cute.

And giving a big middle finger to all of the advertisers and haters that took your other two covers away.

Claire Sinclair: Yeah, definitely. There could even be one of those dialogue bubbles that says, “Look, I’m 21 now—now what?” [Laughs.] Hopefully I can get on the cover next year. Fingers crossed.

Well, I’d think that holding the Playmate of the Year title is a pretty solid consolation prize for losing out on covers, no?

Claire Sinclair: [Laughs.] Oh, yeah, definitely. Beggars can’t be choosers, right? It’s been awesome. Not for a second did I ever think that I had a shot in Hell, because of my age and I’m just a very different mold than the other Playmates of the past year. I thought, “I’m just so different—there’s just no way.” I was really surprised that I even got Playmate in the first place, so this recent was very shocking.

Was it difficult to get your foot in the door, so to speak, and become a Playmate last year? Just two years ago, you were a high school student, and now you’re Playmate of the Year—it seems like it’s all happened really fast for you.

Claire Sinclair: You know what? Seriously, right before I did Playboy, I did… You know right in front Grauman’s Theater in Hollywood, where the characters pose for tips? Have you ever been there?

Yeah, the old Chinese Theater. I saw Batman get into a shoving match with Charlie Chaplin there once.

claire-sinclair-graumans-theaterClaire Sinclair: [Laughs.] Yeah, exactly! Well, I was there everyday posing as Belle, from Beauty And The Beast, for tips. And that was literally two weeks before I got introduced to Hef. We were like bums, essentially. My sister was there with me—she was Cinderella. It’s just so funny how your life can change so dramatically. We were just looking at that as a cool summer thing to do, to make cash. And then, a couple weeks later, I’m being introduced to Hef and I become a Playmate. My world changed so dramatically.

At the time, I was modeling for a pin-up artist, and she introduced me to Hef. It went really fast after that. My pin-ups that I did were in the magazine, and then we did the E! pilot The Bunny House, and then I met Holly Madison and started appearing on her show with her. It just seemed like everything started to move really, really fast after I got Playmate. I moved into the Bunny House across the street from the mansion. So, yeah, it’s been a whirlwind. It’s been a crazy two years full of things that I never thought could’ve happened so soon after high school.

Those days in costume outside the Chinese Theater must’ve been surreal. There are some nutty people walking around that area.

Claire Sinclair: It was pretty cool, actually. We formed this big community, and we’d all hang out afterwards. There were like 30 characters at any given time. It’s hilarious, they’ll just sit on the curb and eat pizza while dressed like Betty Boop or Wolverine. And they’re all over the place like horseshit on that street.

Can anyone just show up there in a costume and join the crowd, or is there some kind of initiation you have to go through?

Claire Sinclair: It’s weird, you can’t step on anyone’s toes. It’s really political. My sister’s boyfriend showed up as Elmo as one day, and there was already an Elmo there. But he was, like, a grungy-ass Elmo; his suit was disgusting and old. My sister’s boyfriend’s Elmo suit was brand-new, fresh, and red, and the older Elmo got really pissed off. He almost got into a physical fight with my sister’s boyfriend. [Laughs.]

You can’t even be in the same genre; if you’re going there as a superhero, the other superheroes have to welcome you into their clique, or you’re going to get shit for it.

Did you just take a shot in the dark and show up as Belle, or did you scope the scene out first?

Claire Sinclair: There was another Belle, but she came very rarely, so I had the territory pretty much claimed as m own. [Laughs.] But there was another Cinderella who hated my sister. They would get into fights all the time.

How has your life changed from all of that since the Playmate of the Year announcement?

Claire Sinclair: I’ve been seeing a lot more opportunities pour in, things I haven’t expected to come my way. I’m getting the chance to read for this really cool indie movie that Kristen Stewart’s mom—Kristen Stewart from the Twilight movies—is directing; she’s been a big editor on a bunch of movies, and this is going to be her directorial debut. So, I’m reading for the part of the “Trophy Wife” next week, and I never would’ve gotten that opportunity. It’s not like a call like that would have come in when I was just a regular Playmate.

During the end of summer, I’m going to very, very busy. We’re working on a stage act right now, too. Since I’m under 21, I can’t do club promotion; the only way I can do club promotion is if I’m an entertainer at the club, so we’re working on a burlesque act that I can perform in clubs and be able to travel around and not miss out on anything. We’re just trying to utilize the title as much as possible, because it’s only for a year—you really got to strike while the iron is hot.

It’s so amazing that I’m becoming a burlesque dancer, though. I did Crazy Horse Paris, which is a really beautiful burlesque show in Las Vegas, and I never thought I’d ever get an opportunity to do that, either. The opportunities I’ve had over the last year have been unreal.

You’ve made no mystery about the fact that Bettie Page is your idol, and she was known for her pin-ups and burlesque shows, so that must be really cool for you to channel some of that Page-ness on stage. Where does your fascination with Bettie Page and the old pin-up culture come from?

claire-sinclair-bettie-pageClaire Sinclair: Ever since I was a child, I’ve been interested in vintage things. My mom used to watch Time Warner Classics, and films from the 1960s and 1940s would come on and I’d just sit there in awe of the way people dressed. I’d see the transformations from the ’40s to the ’50s to the ’60s, and I was just blown away by how things have changed.

I used to go to a bunch of different thrift stores while I was in high school and dress in clothes from various different eras. I rant he gamut in just dressing like I was from different time periods, and I took a particular liking to the styles of the ’40 and ’50s mainly because of the pin-ups. My dad had pin-ups on our walls, and I loved them. They just seemed like the “quintessential woman.” They were fun, and they had themes. I always wanted to pose like that.

It’s so weird how that’s exactly what I’m doing right now, too. My Playmate of the Year spread is all pin-up-inspired; it’s based off of the most famous pin-ups in the world. It’s crazy how everything has come full circle.

You seem to be at the forefront of a pin-up resurgence. Why do you think the look and feel of those vintage pin-ups aren’t all that prevalent today?

Claire Sinclair: It’s inevitable, you know? Things change with the times. From the ’50s, when people wore big poodle skirts that were puffy and considered to be conservative, and then in the ’60s the miniskirt came out, and people started showing skin. Look how dramatically things changed just within those ten years. And now we’re in a completely different time, but I think anyone can still look at a pin-up and appreciate it and thinks it’s beautiful and fun.

Pin-ups will always be relevant. You can never go wrong recreating that era. It’s true, it’s not as huge as it used to be, but it’s still relevant. That’s why I’m able to do it, because people still respect it. So I’m lucky that people still have an interest.

As far as the burlesque show you’re working on, is it going to be anything like that Christina Aguilera movie, Burlesque? Hopefully not, because that movie sucked.

Claire Sinclair: [Laughs.] It’s funny, all of the people I worked with in Crazy Horse kept saying, “That movie is crap! It doesn’t represent burlesque well.” And I think it does, actually. They actually have a song in it called “I Am A Good Girl,” and that’s one of Crazy Horse’s original songs. So, yeah, it’s in a similar light. I can see the comparisons. It’s a lot of fun. But, yeah, that movie is basically a really watered-down version of the burlesque I’m going to do.

Is being a Playmate of the Year a 24/7, seven-days-a-week job?

Claire Sinclair: No, I tell everyone that Playmate of the Year doesn’t come with a set of things that you have to do throughout that year. You still have to go out and look for opportunities; it’s not like there are tons of jobs thrown your way within Playboy. There are a couple of obligations every month within Playboy, but it’s not like you have to work fulltime for them.

I’m lucky in the fact that things are spinning for me right now and there are a lot of things coming, but it’s really about making sure that you stay relevant. You really have to hustle.

Last year’s winner, Hope Dworaczyk, was a cast member on the most recent season of Celebrity Apprentice. Are you looking for gigs in that vein?

Claire Sinclair: I definitely want to do Dancing With The Stars. [Laughs.] It’d be like burlesque, when they taught me ten hours a week, so I think I’d be used to the training, and that I’d do really well on that show. I’m not a dancer—that’s the thing. I’m not confident with it, but I know that if I was trained, I could do it, and win. [Laughs.]

We’d vote for you, no question. Switching gears a bit, in your Playboy profile, you mention that the kinds of guys that you find are sexy are “man-boys.” We’re not sure if that’s a positive or negative description.

claire-sinclair-bed-nakedClaire Sinclair: [Laughs.] It’s totally a compliment! I like guys who are youthful; they don’t have to look like a little boy, particularly, but they just have to act really youthful. Childlike guys, guys who are curious—I think that’s adorable. I can’t date someone who has a really serious tone; I need someone who’s not afraid to act like a man-boy.

That actually plays into your willingness to dress as a Disney character in public, too. Would your heart melt if a boy-ish-looking guy showed up for a first date in a Spongebob Squarepants costume?

Claire Sinclair: Yeah, I’d love it. [Laughs.] It’s just more fun that way. Who wants to be with someone who’s all serious? Someone who can’t have fun and can’t goof around. The most attractive quality in a man, I think, is when they can be enthusiastic about the littlest things.

So, for instance, a guy whose idea of a great date night would be to buy you a ticket to see X-Men: First Class with him and school you on all of the mutants’ back-stories? Because I could totally do that.

Claire Sinclair: Yeah! [Laughs.] That’d be sexy as hell. It could be anything, though. Just someone who’s still excited by things and has a really optimistic outlook. They have to be boy-ish in their personality.

These days, you must be receiving tons of outspoken attention from guys everywhere. Is that something you’re comfortable with?

Claire Sinclair: It takes some getting used to, because prior to all of this I wasn’t getting that kind of attention. All of the sudden, I’m at these parties and guys come up to me and tell me that they’ve seen me naked. [Laughs.] It’s definitely a weird feeling, but you definitely get used to it quick.

The most interesting thing to me is seeing who comes out to my signings. All I get at my signings, seriously, are pre-teen girls and boys and then middle-aged to older men—they are no men of my own age there.

The older men, in particular, could be gravitating toward you due to your whole old school pin-up vibe.

Claire Sinclair: Definitely, yeah. They’re a huge fan base for that look, because I think it brings them back to the feelings they had when they were younger. And you know what? I love that!