After six and a half decades in hiding as Bruce Jenner—the Olympic champion and model of all-American masculinity—Caitlyn Jenner introduced herself to the world Monday, on the July cover of Vanity Fair. In sumptuous photographs by Annie Leibovitz, Caitlyn reveals herself as an elegant beauty, comfortable in classic silhouettes, pinup poses, and Old Hollywood aesthetics. 
 
 And just who helped Caitlyn decide upon her introductory look? Vanity Fair’s veteran fashion & style director, Jessica Diehl, who has styled countless covers for the magazine, ensuring that each subject looks and feels his or her best. In celebration of Caitlyn’s grand unveiling today, VF Hollywood connected with Diehl to hear how she and Jenner collaborated on Caitlyn’s very public coming out, the James Bond–esque precautions taken on this top-secret shoot, and what screen sirens helped inspire Caitlyn’s glossy first impression. 
 
 VF Hollywood: I can’t believe that you kept this a secret for so long. 
 
 Jessica Diehl: It was not easy. I am getting a lot of angry text messages from friends, colleagues, and acquaintances. 
 
 How long did you have to style this cover? 
 
 Not that long [and] we couldn’t really prepare the way we normally prepare. Normally we go to, I don’t know, Valentino or Armani, and say we are shooting a cover and ask if they can give us some clothes [to borrow]. For this, I had to go into stores incognito, so to speak—not like anyone would know what I looked like anyway—and buy stuff. That was actually what was fun. It was like Vanity Fair: Off the Rack. 
 
 Did you talk to Caitlyn beforehand to discuss the look? 
 
 Yes, I went to go meet her before just to talk through what she wanted to do. Just because the Vanity Fair thing—it’s a very specific look. It is not your casual-jeans Tuesday. But we also just wanted to talk about her style in life. Coming from a very fashion-forward family, we sort of thought that the nicest thing to do was to focus on style over fashion. Nothing too bling or too shiny. Kind of keeping it more in the style arena rather than hardcore fashion arena . . . 
 
 To get special early access to the revealing story and stunning photographs now, before the issue hits newsstands on June 9, subscribe to Vanity Fair’s digital edition. 
 
 Were you talking at her house in Malibu? How long did the meeting last? 
 
 I went to her house and stayed there for a couple of hours maybe, and just spent the time talking through things and bringing up lots of pictures and inspiration images, from Lauren Bacall to The Thomas Crown Affair to people who I think look amazing on the red carpet. And just vintage photographs of Old Hollywood stars. A couple of Jackie Kennedys are never wrong. And then for the photo shoot, we talked more about how one would see oneself in an ideal world in Vanity Fair. 
 
 You mentioned that you showed Caitlyn some inspiration images. What were some of Caitlyn’s own inspirations or ideas for how she wanted to look? 
 
 She’s all-American in so many ways. She has certain ideas about what she feels great in. But those ideas are still forming and taking shape. There will be some experimentation and trying things. Welcome to the world of women’s fashion! It’s not always smooth sailing, but I think she has a pretty good idea of what makes her feel good, and those are classic silhouettes. She has a fantastic physique. It’s just a totally well-taken-care-of physique. She’s an athlete, so the muscle tone is incredible. She’s slim, and her proportions are very easy to dress. 
 
 The Kardashian family is known for clingier, more risqué styles. But Caitlyn is kind of wanting to keep her style classy and elegant? 
 
 Yes, and that is no disrespect to the Kardashian clothing choices at all. It’s just that feels more comfortable to her. Not to say that she won’t rock a sexy Roland Mouret number. She would love it. But there is definitely a more restrained feeling so far. Hopefully she’ll get to just have fun with it rather than have the fashion police judging what she wears every day. I think the most important thing here is that she gets to have fun and finally do things she’s been wanting to do. For all I care, she could wear a purple striped muumuu dress that would be a fashion failure. But if that is a happy moment for her, that is a success to me. 
 
 I would love to ask you about the styling on the cover specifically. Both you and Caitlyn knew how important this image was going to be—culturally, and also, this is the world’s first impression of her. What was your vision for the cover look? 
 
 It had a lot to do with the idea that there is so much artifice everywhere in the world and the world of red-carpet dressing, and even with magazines, there is artifice in everything we do. That can be wonderful because it is fun. But there was a stripped-down idea there that sort of felt like underneath all of this excitement and newsworthiness is the soul of a woman. And that didn’t need a lot of covering up. It was not meant to be risqué in any way. It was really meant to sort of show with all honesty and purity, “This is what is going on. Here I am.” 
 
 There is already a report online speculating that Caitlyn wanted to show off her body so that there would not be any more questions from the public about what her body looked like. Was that a discussion at all? 
 
 It was not so much a discussion with us. I think Annie and Caitlyn and all of us sort of went at it from the perspective of this is her moment to be in her own skin. We’re not going to take a nude photograph. I don’t know if that report is completely right. I think it is a positive side effect. The one thing that you don’t really need after months and months of speculation is further intrusiveness. I think the only way to counter that is to be open and honest. I think that is what the Diane Sawyer thing was about. It is really Caitlyn embracing that she is free. 
 
 To get special early access to the revealing story and stunning photographs now, before the issue hits newsstands on June 9, subscribe to Vanity Fair’s digital edition. 
 
 You mentioned how much harder it was to style this cover because of the secrecy involved. Can you talk about some of the James Bond–esque precautions you had to take while preparing for the shoot? 
 
 Well, my poor office thought we were doing Barbra Streisand! I just couldn’t think of anyone tall. [Laughs] And I don’t even know if Barbra Streisand is tall, but in my mind she was tall. And so that just seemed right. I should have said Rene Russo, who I think [Caitlyn] looks like more anyway. The secrecy, I have to say, had a lot to do with being discreet and shopping—a lot of which we did online. We talked to no one. Literally, the people here at Vanity Fair did not know. Three people in the fashion department knew, including me. 
 
 Did you have other looks you considered for the cover or was the corset the clear forerunner? 
 
 We tried everything. We had basically a three- or four-hour fitting. I have to say, out of that three- or four-hour fitting, there were only two things we did not like. Everything looks good on her. That just doesn’t happen. It was never the clear forerunner—it just kind of became clear when we spent the day together. Annie, I am sure, had it in her mind [what the cover was going to look like] way before. Annie always has the thing in her mind way before and lets it all unfold, and then we all take credit for it. The off-the-shoulder Zac Posen was really beautiful. But then, all she really wanted to do was be open and honest. That is how that look felt. 
 
 In the cover story, V.F. contributing editor Buzz Bissinger mentions how comfortable Caitlyn was throughout the cover shoot. Is that the sense that you got? 
 
 Absolutely. I’d like a slice out of that confidence pie. She was comfortable, confident, and has absolutely no reason not to be. It was probably the most exciting thing to see—there was real joy in her feeling comfortable and happy in her skin. It was amazing. I don’t usually get super-sentimental about things, but that was probably the most emotional and open experience I have ever had on a shoot. 
 
 You have styled so many incredible covers over the year, but what did this landmark cover—landmark moment—mean to you personally? 
 
 Everyone’s reactions have been super-personal because you can only imagine what a life not lived in openness and in your skin would be like. We can all kind of find things that made us feel uncomfortable in our skin. And to see someone letting all of that go and just being completely at home and at peace with themselves is something everyone wishes they could have. You felt an incredible sense of responsibility. I didn’t want her to feel in any way that this wasn’t . . . this was meant to be the most fun she was ever going to have on a shoot. And that was utopic. And she will probably have even more fun [on future shoots because there will be less at stake]. 
 
 It was really meant to feel like the most “welcome to the club” kind of experience. I can’t describe it—we all bawled our eyes out at the end. And I am not a crier. It was the most personal experience. It was more than just taking pictures. 
 
 WATCH: Caitlyn Jenner Is Grateful to Laverne Cox and Other “Pioneers” 
 
 To get special early access to the revealing story and stunning photographs now before the issue hits newsstands on June 9, subscribe to Vanity Fair’s digital edition. 
 
 Related: Introducing Caitlyn Jenner ||||| Who knew the gossipy, overexposed, selfie-taking Kardashians could be so good at keeping a secret? 
 
 Vanity Fair unleashed one of the biggest cultural stories of the year on Monday with Caitlyn Jenner's first public interview and photo shoot. The exclusive captivated the media world with a speed and intensity matched by few other articles. 
 
 For Vanity Fair, Jenner and her family, it marks the result of months of negotiations and work, as well as beefed up security to keep the story from leaking. The magazine hired security for the shoot and forced people to give up their cell phones to prevent anything from leaking. A spokesperson for VF told Mashable that the magazine had been in talks with Caitlyn Jenner since January and did not give her any compensation for the exclusive. 
 
 The magazine was concerned about leaks and took security measures "every step of the way," including on the photo shoot, in the VF editorial office and at the printing plant for the upcoming issue. The story and pictures were done on a single computer that was never connected to the Internet, with the assets put on a thumb drive every night and then deleted from the computer. The story was even hand-delivered to the printer. 
 
 The magazine's exclusive on Jenner's introduction as Caitlyn spread far and wide on Monday, with media outlets as diverse as ESPN, Reuters, Seventeen magazine and the New York Times following the story. VF's original tweet of the cover has been retweeted more than 145,000 times in approximately four hours. 
 
 Plaudits rolled in for VF throughout the day. 
 
 If I worked at @VanityFair, I wouldn't have been able to sleep all weekend. Quite the Monday coup. #CaitlynJenner — Jeffrey David Cook (@jdc3sa) June 1, 2015 
 
 EXCLUSIVE: leaked footage inside the vanity fair offices right now #CaitlynJenner pic.twitter.com/cge9qmak8M — Twillo Art (@TwilloArt) June 1, 2015 
 
 Jenner first came to national attention after she won a gold medal in the decathlon during the 1976 Summer Olympics. At the time, she identified as Bruce Jenner. She has more recently been known for her role on Keeping Up with the Kardashians, during which she said she self-identified as a man. 
 
 Jenner and her family might seem overexposed in the media, considering they have their own dedicated reality show and hardly a week goes by without one of the family members gracing a magazine cover. But that shouldn't be mistaken for media naiveté. Jenner and the rest of the clan are well versed in how to handle big announcements. 
 
 The New York Times in a recent feature on Kris Jenner noted that the family had plenty of experience in planning and executing media exclusives for maximum impact. The article noted that none of the Kardashians had leaked Jenner's transformation in the promos for the new season. 
 
 "Bruce has no privacy; none of them do. That’s the deal they made with one another. When they’re silent on Bruce, they aren’t protecting him from the judgments of a cruel world; they are protecting Bruce’s exclusive," wrote Taffy Brodesser-Akner in the article. 
 
 The VF article with Jenner is her second in which she discussed her transition, having told Diane Sawyer in late April that she now self-identified as a woman. 
 
 That Vanity Fair cover is stunning. Coupled with the Sawyer interview, I'm almost as awed by Jenner's media strategy as I am her bravery. — Gina Trapani (@ginatrapani) June 1, 2015 
 
 VF's particular brand of celebrity-drive journalism has held up as other magazine have struggled to make the transition to the Internet. The brand's combined print and digital audience has risen 17% in the first quarter of 2015 when compared to the same period a year ago and has more than double its mobile audience, according to the Association of Magazine Media's 360° report. ||||| share tweet pin email 
 
 Buzz Bissinger, who authored the upcoming Vanity Fair article reintroducing Bruce Jenner to the world as "Caitlyn," can already sense the freedom Jenner has felt since making the transition. 
 
 "A huge difference,'' Bissinger told Savannah Guthrie on TODAY Tuesday. "More open, more honest, more connected, more everything. I think Caitlyn has found her soul that really Bruce never had. I just spoke to her yesterday and she said, 'I'm free. I can live. I don't care about the paparazzi any more - just make sure it's a good shot.''' 
 
 The cover of the July issue of Vanity Fair revealing Jenner to the world as Caitlyn features her in full makeup and a strapless corset in a photo by Annie Leibovitz. 
 
 "If I was lying on my deathbed and I had kept this secret and never ever did anything about it, I would be lying there saying, 'You just blew your entire life,'" she says in the Vanity Fair interview. 
 
 Vanity Fair 
 
 As Jenner has made the change to becoming Caitlyn, there has been speculation over how much her ex-wife, Kris Jenner, knew about Bruce's desire to transition to a woman. 
 
 In the article, Kris Jenner asks, "Why would you want to be married and have kids if this is what you wanted since you were a little boy? Why would you not explain this all to me?” 
 
 However, she also said that Bruce told her in the early 1990s that he had taken hormones in the early 1980s. Caitlyn contends in the story that Kris witnessed her cross-dressing while she was living as Bruce, while Kris denies that ever happened. 
 
 "Kris was very civil during the interview and she was very open,'' Bissinger said. "She said, 'I didn't know...I had no idea about the extent of his gender issues, really the severity.' I've got to say, I think she's right. I think Bruce downplayed it (as) 'It was a phase of my life, it's over.' It wasn't over, and I think Kris had a sense that whatever happened in the past I can fix it." 
 
 Caitlyn expressed regret about not being a good father as Bruce to his four children from two previous marriages before he married Kris Jenner, saying she was often absent from their lives. 
 
 "One of the beautiful parts of this is that as Caitlyn, they are trying really hard to reconnect,'' Bissinger said. "It's not easy, but they are really trying." 
 
 Her children from her first two marriages, Burt, Cassandra, Brandon and Brody, have also declined to appear in an upcoming E! reality show documenting her transition. 
 
 "They felt they could've gotten money from it, they could've gotten exposure from it,'' Bissinger said. "They said, 'Dad, you have the ability to have a legacy as a sports figure equal to Muhammad Ali. You could be a real trailblazer here in becoming a woman, in becoming a transgender woman, don't blow that with spectacle.' They said, we do not want to participate, and they must have been asked a dozen times." 
 
 In revealing herself as Caitlyn on Monday, Jenner also started a Twitter account that set a record for reaching more than one million followers in a matter of hours. 
 
 Another Jenner world record, and at 65? Who'da thought! Humbled & honored to have reached 1M followers in 4 hrs. Thank you for your support. — Caitlyn Jenner (@Caitlyn_Jenner) June 1, 2015 
 
 I'm so happy after such a long struggle to be living my true self. Welcome to the world Caitlyn. Can't wait for you to get to know her/me. — Caitlyn Jenner (@Caitlyn_Jenner) June 1, 2015 
 
 Vanity Fair also released a behind-the-scenes look at the photo shoot for the issue that hits newstands on June 11. 
 
 "Bruce always had to tell a lie,'' she says in the video. "He was always living that lie, Every day, he always had a secret, from morning till night. Caitlin doesn't have any secrets. Soon as the Vanity Fair cover comes out, I'm free." 
 
 Many of Jenner's family members took to social media to express support for her after the magazine cover had been unveiled, including the daughter of the Olympic great. 
 
 be free now pretty bird. — Kendall Jenner (@KendallJenner) June 1, 2015 
 
 Follow TODAY.com writer Scott Stump on Twitter and Google+. ||||| Welcome back to Midweek Madness! Every Wednesday, we frolic through the tabloid forest in search of merry critters bearing gossip. This week, Eva Longoria is dating a political figure; Jennifer Aniston is having twins again; Bethenney Frankel is getting divorced; and Britney Spears is off her meds. Lay yourself down on the mossy banks of the bubbling brook and let's do this. 
 
 Ok! 
 
 "Yes, I'm Pregnant — With Twins!" 
 
 Please do not be shocked when you open this magazine and find that there are NO DIRECT QUOTES from Jennifer Aniston. Merely this sentence: "Friends say Jen is not only pregnant at last, but that she and fiancé Justin Theroux are expecting twins — a boy and a girl." An "insider" claims her fertility treatments worked, Jennifer Aniston does not utter the words "Yes, I'm pregnant." BTW! Star had this exact same cover line in December 2011. And before that, in 2008, when Jen was supposedly incubating John Mayer's twins. Even if she does have a fetus a-cookin' — multiple mags are saying so — this "quote" is not a quote. 
 
 Grade: F (vulture) 
 
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 Life & Style 
 
 "She Said 'No'!" 
 
 At the end of November, Star magazine claimed that that Scott "American Psycho" Disick proposed to Kourtney Kardashian on a bridge in Paris, and she said yes, and their wedding would be televised. This cover story claims that Scott popped the question in Miami, it was not filmed, and Kourtney said no. She doesn't want to be engaged. Moving on! Taylor Swift might come between Harry Styles and "his band," One Direction, because they're going on tour in February, and if Harry tries to see TSwizzle between shows, he could end up tired and jet lagged and RUIN EVERYTHING. A source insists they will break up before the tour begins. Katy Perry and John Mayer were spotted being "quite affectionate," but what she doesn't know is that he has a jumpoff on the side. He and this mystery lady — whom he's been seeing since early 2011 — meet "frequently," just for sex, and they sext each other constantly. A source says Katy will be devastated if she finds out — and wouldn't it be terrible if she found via Life & Style? Next: Lamar Odom isn't wearing his wedding ring anymore, dun dun DUN. Jessica Simpson and Eric Johnson might buy the $13.5 million mansion currently owned by Ozzy and Sharon Osbourne. Barbara Plavin, the Victoria's Secret model Justin Bieber flirted with backstage during the fashion show in November, posted a picture of herself in front of Beebs's tour bus in Miami earlier this week. Bethenny Frankel and Jason Hoppy are getting divorced. And lastly, Bradley Cooper is "ready" to propose to Zoë Saldana. Hate to lose him, but she's so great. 
 
 Grade: D (badger) 
 
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 In Touch 
 
 "The Rings Are Off!" 
 
 Lamar Odom went out and failed to take his wedding band with him, which "humiliated" Khloe, because jewelry has power! Meanwhile, Bethenny Frankel has also stopped wearing her wedding ring, and a source claims she's told husband Jason Hoppy that "they are done." She's meeting with lawyers and is "embarrassed," because she hates to fail. Also, since she made $120 million off of her cocktail line, there are millions at stake. Also inside: Taylor Swift is "breaking up the band" by dating Harry Styles; a sidebar compares her to Yoko Ono, Britney Spears and Jessica Simpson, who destroyed The Beatles, NSync and 98 Degrees. (Which one of these things is not like the other?) (Fig. 1) On the cover, there's a picture of Teen Mom's Catelynn and the word "split," but inside, you find out that she and Tyler were apart because he flew to New Orleans for a job opportunity. They are back under the same roof right now, though, so don't fret. Last, but not least: The best story in this issue uses Photoshop to give celebs new hairdos. (Fig. 2) I did Virtual Makeover once and gave myself Snooki's hair. Who doesn't love a makeover? 
 
 Grade: D+ (skunk) 
 
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 Star 
 
 "Sleeping Together!" 
 
 Reading between the lines of this Katie Holmes/Tom Cruise cover story took a LOT of effort, and it's still unclear exactly what's going on. Apparently Tom and Katie met in New York to discuss Suri's Christmas and little Joey Potter felt a "surge of emotion" when she saw him, and "one thing led to another," which we are supposed to interpret as P in V. Anyway, Katie "had to admit" that it felt good to be in Tom's arms again, says a source who, I guess, is a fitted sheet? And so Tom suggested Suri, Katie and he spend Christmas together in their old Telluride mega-cabin, just like old times, praise Xenu. Next! Anne Hathaway wants a baby and may already be pregnant. A "scary-skinny alert" has been issued for Selma Blair. Kirstie Alley is going to let Millionaire Matchmaker Patti Stanger set her up with an "age-appropriate gent." Eva Longoria is dating L.A. mayor Antonio Villaraigosa; sparks flew when they were both trying to get Obama reelected, and were recently seen holding hands at a late-night showing of Lincoln. Positibely Presidential! Taylor Swift is "bored" of Harry Styles because "they really have nothing to talk about." And finally, if this is true, it sucks: A headline claims Britney Spears is off her meds. She was spotted in a Rite Aid in L.A., throwing a tantrum because she wanted to buy a shopping basket full of body lotion, but Jason Trawick told her it was a waste since she'd never use it and had lots of nicer products at home. She "began stomping her feet and yelling at him in this strange little-girl voice" a spy claims, and "sources say" she's gone off her antipsychotics and is very upset, in general, because she wants another kid and Jason doesn't want to father her child — or at least, wants to wait. In sick, twisted sidebar, the mag gleefully asks, "Will Her New Meltdown Be This Bad?" and prints pictures of her shaving her head and hitting a car with an umbrella. Rude. (Fig. 3) 
 
 Grade: C (beaver) 
 
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 Us 
 
 "We're Having A Baby!" 
 
 Looky here! Jenna Dewan-Tatum gives an interview to the magazine, confirming that she's got a little bun in the oven and gushing: "Channing's going to be the best dad." These two, who met on the set of Step Up, seem genuinely in love and adorable; they have matching tattoos ("side by side" in Balinese and also the word "twin"under their wedding rings) and for his birthday she organized a Dirty Dancing flash mob singing "I've Had The Time of My Life." CUTE. Anyway, Jenna's final words on the kid: "It's going to come out dancing!" Also inside: Rita Ora had a secret fling with Jonah Hill, who, of course, bragged about it, and the news got back to her on/off boyfriend Rob Kardashian. Taylor Swift and Harry Styles are "crazy in love" and might just get married all of a sudden. Insert a Ms. Jay horrified eyes gif here. Finally, Katy Perry introduces John Mayer as "my boyfriend," and a source says "they are seriously in love and exclusive." Does John know? Oh, and backhanded compliment of the day: "John is surprised at just how cool and smart she is." Pretty and hot gals are usually dumb as a doornail, hmm, Johnny? 
 
 Grade: A (bunny) 
 
 Addendum 
 
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 Fig. 1, from In Touch 
 
 Fig. 2, from In Touch 
 
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 Fig. 3, from Star
– The New York Times sheds a little more light on what went on behind the scenes of Caitlyn Jenner's super-secretive Vanity Fair cover shoot, via the paper's conversation with Jessica Diehl. Diehl, VF's fashion and style director, says she found her job "completely petrifying," partially because in depicting Jenner, Diehl wanted to nail "how she sees herself," she explains. And then there was the secrecy: Only about 10 people at the magazine knew Jenner was being photographed; Diehl told the rest of the team Barbra Streisand was the subject of the shoot. And, because of the need for secrecy, Diehl had to buy rather than borrow some of the clothing for Jenner to wear—a challenge for a 6-foot-2-inch cover model. One dress was sourced traditionally from Zac Posen, and the designer didn't realize he was going to be part of such a "historic moment," as he later called it, until he saw the magazine Monday morning. More news: In case you were wondering why Caitlyn didn't go with Kaitlyn, in a nod to ex-wife Kris, stepdaughters Kim, Khloe, and Kourtney Kardashian, and daughters Kylie and Kendall, well, she's not saying. But, as the AP reports, Caitlyn does acknowledge in the full VF interview that she at least considered the "K" spelling before deciding to break the tradition. Jenner's mom is having a hard time adjusting to all the changes: Caitlyn is "beautiful" and "so much more at ease," Esther Jenner tells Access Hollywood, but "I still have to call him Bruce. His father and I named him that. It's going to be a struggle for me to get used to the change, but happily so … I'm very happy for him—or her!" Caitlyn seems to have overshadowed Kim Kardashian's pregnancy news, but a source tells the New York Daily News that Kim and Kanye are expecting not one but two babies. "Kim has told a handful of people that she had in vitro and that two eggs were fertilized. She is waiting to see if they both 'stick' before she makes any kind of announcement," the source says, adding that Kim also doesn't want to take away from Caitlyn's moment. Another source tells E! the due date is December. Click to watch a promo for Caitlyn Jenner's upcoming reality show.