Caitlyn Jenner Celebrates Her 66th Birthday on the Red Carpet
![Caitlyn Jenner walked the red carpet at Logo TV’s “Beautiful As I Want To Be” web series launch party at The Standard Hotel on October 27, 2015 in Los Angeles, California.](https://s.yimg.com/ny/api/res/1.2/5A3K_Mizat3OOITx._tofA--/YXBwaWQ9aGlnaGxhbmRlcjt3PTk2MDtoPTEzOTY-/https://s.yimg.com/uu/api/res/1.2/bcdkDHTLWV1qA77JC69Ppg--~B/aD0zMDAwO3c9MjA2MzthcHBpZD15dGFjaHlvbg--/https://41.media.tumblr.com/bc1f6cbabbae4e949a05b4204a7efd48/tumblr_inline_nwxlz8o0XJ1rpqds5_1280.jpg)
Caitlyn Jenner walked the red carpet at Logo TV’s “Beautiful As I Want To Be” web series launch party at The Standard Hotel on October 27, 2015 in Los Angeles, California.
For her birthday on October 28, Caitlyn Jenner celebrated the night before by walking a red carpet in a black velvet dress. She paired the long-sleeved piece with open-toe heels, showing off her bright pink pedicure, a white clutch, and diamond earrings. Chandi Moore, Candis Cayne, and Geena Rocero were all in attendance as well.
![Caitlyn Jenner addressed the audience during the Point Foundation’s Annual Voices On Point Gala in Los Angeles, California.](https://s.yimg.com/ny/api/res/1.2/WHXghr7ZBE9R5wr6i94fpg--/YXBwaWQ9aGlnaGxhbmRlcjt3PTk2MDtoPTk2Mw--/https://s.yimg.com/uu/api/res/1.2/bqmyYgaCwyC8WrLRr6LRXw--~B/aD01OTk7dz01OTc7YXBwaWQ9eXRhY2h5b24-/https://41.media.tumblr.com/ac3cf0b79b39b61348d03c099f4c63ed/tumblr_inline_nwxm52SzGe1rpqds5_1280.png)
Caitlyn Jenner addressed the audience during the Point Foundation’s Annual Voices On Point Gala in Los Angeles, California.
To present the producers of the ABC Family docuseries Becoming Us and Rhys Amazon’s Transparent with an award, Caitlyn Jenner wore her best power suit and channeled Jennifer Aniston’s Gucci suit moment earlier this year.
![Caitlyn Jenner in a white dress at?the 8th Annual Safety Harbor Kids Polo Classic Fundraiser at Will Rogers State Historic Park in Pacific Palisades, California.](https://s.yimg.com/ny/api/res/1.2/BNdaBWc1DJ59KQA3rFSD8w--/YXBwaWQ9aGlnaGxhbmRlcjt3PTk2MDtoPTEzOTE-/https://s.yimg.com/uu/api/res/1.2/ZCCMsNObPXtQfWlV7CqbAA--~B/aD0zMDAwO3c9MjA3MDthcHBpZD15dGFjaHlvbg--/https://40.media.tumblr.com/2f42fe216e4be6bb30ad39b76c396341/tumblr_inline_nwxlyp1qnL1rpqds5_1280.jpg)
Caitlyn Jenner in a white dress at the 8th Annual Safety Harbor Kids Polo Classic Fundraiser at Will Rogers State Historic Park in Pacific Palisades, California.
For an end of summer soiree, Caitlyn Jenner gave a white linen dress one last run. She paired it with a gold belt, wedge sandals, and round sunglasses.
![Caitlyn Jenner in Moschino.](https://s.yimg.com/ny/api/res/1.2/bfNFpinKk8iaqNcb55Hmjg--/YXBwaWQ9aGlnaGxhbmRlcjt3PTk2MDtoPTEyOTY-/https://s.yimg.com/uu/api/res/1.2/u4rOWvfvNMUhKx.w1NB1MQ--~B/aD0zMTAwO3c9MjI5NzthcHBpZD15dGFjaHlvbg--/https://40.media.tumblr.com/b2d68474ad9a625aae33eaaf144ac1ab/tumblr_inline_nv7uktKRPA1rpqds5_1280.jpg)
Caitlyn Jenner in Moschino.
Out to dinner in Los Angeles with friend Candis Cayne, Caitlyn Jenner served up fall style inspiration. Wearing all black — a pair of leather pants, black wrap jersey top, and knee-high boots — she took the monochromatic look to the next level with a Moschino jacket. The black and white bold-lettered coat was certainly a statement piece, and Jenner rightly paired it with a simple outfit.
![Caitlyn Jenner in a black jumpsuit.](https://s.yimg.com/ny/api/res/1.2/O_EQT29zHzKzHKMoUiu1lQ--/YXBwaWQ9aGlnaGxhbmRlcjt3PTk2MDtoPTE2NjU-/https://s.yimg.com/uu/api/res/1.2/nbjPXktRcxsR_fNi6sthog--~B/aD0zMDAwO3c9MTczMDthcHBpZD15dGFjaHlvbg--/https://41.media.tumblr.com/86b7df9403917a389034bdf2895b20f9/tumblr_inline_nv7ukv8w7v1rpqds5_540.jpg)
Caitlyn Jenner in a black jumpsuit.
Caitlyn Jenner’s docu-series "I Am Cait” premiered on Sunday to huge numbers signaling a success, so it’s only natural that she stepped out to celebrate. On Wednesday night, she was spotted at Eva Longoria’s restaurant Beso in Hollywood, California. She dressed for the celebratory occasion, jumping on the jumpsuit trend in a black one piece. Strappy heels showed off her vibrant pedicure and she accessorized simply with three delicate chains.
![Caitlyn Jenner in a gray dress and leather jacket at a Culture Club concert.](https://s.yimg.com/ny/api/res/1.2/9fFGGulmi415mJCDVKrROQ--/YXBwaWQ9aGlnaGxhbmRlcjt3PTk2MDtoPTE0MzU-/https://s.yimg.com/uu/api/res/1.2/HJfGKCcFipaGoGQ70dloYw--~B/aD00MzI4O3c9Mjg5NjthcHBpZD15dGFjaHlvbg--/https://40.media.tumblr.com/40f1eed417869cc2dcd06f7af928d6fb/tumblr_inline_nv7ukwXS1M1rpqds5_540.jpg)
Caitlyn Jenner in a gray dress and leather jacket at a Culture Club concert.
Making a surprise appearance at Culture Club’s performance at the Greek Theatre on July 24, 2015 in Los Angeles, Calif., Jenner wore a gray dress with a leather jacket and knee-high leather boots. She received a standing ovation. Whether it was for her outfit or bravery, remains to be seen.
![Caitlyn Jenner and Laverne Cox meeting for the first time in black and white outfits.](https://s.yimg.com/ny/api/res/1.2/RbhEyIr_YtGZyesvKIMEcQ--/YXBwaWQ9aGlnaGxhbmRlcjt3PTk2MDtoPTg2Ng--/https://s.yimg.com/uu/api/res/1.2/m6HrV7YzfpzJkPNMNPwIFQ--~B/aD01NzA7dz02MzI7YXBwaWQ9eXRhY2h5b24-/https://41.media.tumblr.com/9c355149c1730b426af0b20e6be24a26/tumblr_inline_nv7ukxcV3R1rpqds5_540.png)
Caitlyn Jenner and Laverne Cox meeting for the first time in black and white outfits.
Caitlyn Jenner and Laverne Cox are finally friends IRL! Though the two transgender icons have publicly bantered on social media and spoken on the phone, they only met in person this past Sunday, at a special screening of Jenner’s upcoming E! docu-series, “I Am Cait.” The “Orange Is the New Black” star, who wore a crop top and tight skirt, shared photos from the occasion on Instagram. Sixty-five-year-old Jenner dressed down in jeans and a white blouse. They were joined by a number of other well-known trans women, including Candis Cayne, Zackary Drucker, and Jen Richards.
Following Jenner’s “Vanity Fair" cover reveal, Cox wrote an essay on Tumblr about what the visibility means for the LGBTQ community. "Yes, Caitlyn looks amazing and is beautiful but what I think is most beautiful about her is her heart and soul, the ways she has allowed the world into her vulnerabilities,” the actress wrote. “The love and devotion she has for her family and that they have for her. Her courage to move past denial into her truth so publicly. These things are beyond beautiful to me.”
![Caitlyn Jenner and Laverne Cox with a group of #girlslikethem at a screening of “I Am Cait.”](https://s.yimg.com/ny/api/res/1.2/UIzIXIepNtATql3omknoEg--/YXBwaWQ9aGlnaGxhbmRlcjt3PTk2MDtoPTUzOQ--/https://s.yimg.com/uu/api/res/1.2/qAbZ0bYlz1es.ZVmeBsHyw--~B/aD0zNTk7dz02NDA7YXBwaWQ9eXRhY2h5b24-/https://36.media.tumblr.com/a6a1d71601fbde3439ce5957831a5cec/tumblr_inline_nv7ukyn4Sw1rpqds5_540.png)
Caitlyn Jenner and Laverne Cox with a group of #girlslikethem at a screening of “I Am Cait.”
Fun with #girlslikeus tonight at the screening of #IAmCait @tracelysette @candiscayne @smartassjen @zackarydrucker #MimiMarks #TransIsBeautiful,“ Laverne Cox captioned a group shot taken at a private pre-viewing of Caitlyn Jenner’s "I Am Cait” docu-series. While Jenner dressed down in jeans, Cox wore a crop top and tight skirt.
![Caitlyn Jenner in Diane Von Furstenburg at the Del Mar Racetrack.](https://s.yimg.com/ny/api/res/1.2/P0mXqabod3znG0egyQ6dKg--/YXBwaWQ9aGlnaGxhbmRlcjt3PTk2MDtoPTY4Ng--/https://s.yimg.com/uu/api/res/1.2/sU7HXsI9BIPHiDbLGgHf7A--~B/aD0xMjg2O3c9MTgwMDthcHBpZD15dGFjaHlvbg--/https://36.media.tumblr.com/2b04d69c1a6c012e2ad9e1769a34e8e7/tumblr_inline_nv7ukzG6Cj1rpqds5_540.jpg)
Caitlyn Jenner in Diane Von Furstenburg at the Del Mar Racetrack.
Following her amazing speech at the ESPY Awards, Jenner attended Opening Day of the Del Mar Racetrack in San Diego. To take in the races, she wore a flirty DVF silk wrap dress with a ruffle hem in a red twirl pattern (you can have it too for $468!). She accessorized with an oversized hat and round sunglasses.
![Caitlyn Jenner in Atelier Versace at the ESPY Awards.](https://s.yimg.com/ny/api/res/1.2/iHibafC65Wp46XzIarvWIw--/YXBwaWQ9aGlnaGxhbmRlcjt3PTk2MDtoPTEzMjg-/https://s.yimg.com/uu/api/res/1.2/mxy9P5p94XDuHZ5Mxzy20g--~B/aD00MDk2O3c9Mjk2MDthcHBpZD15dGFjaHlvbg--/https://41.media.tumblr.com/4e3bad29590c81e4188e68d070aae191/tumblr_inline_nv7ul02wtU1rpqds5_540.jpg)
Caitlyn Jenner in Atelier Versace at the ESPY Awards.
To accept the Arthur Ashe Courage Award at the ESPY’s, Cailtyn Jenner, in her first major appearance since coming out as transgender, looked glamorous in a white Atelier Versace gown. “Trans people deserve something vital: They deserve your respect,” Jenner said.. “If you want to call me names, make jokes, doubt my intentions, go ahead, because the reality is, I can take it,” she said. “But for the thousands of kids out there, coming to terms with being true to who they are, they shouldn’t have to take it.”
![Caitlyn Jenner poses in a long black dress for her first “I Am Cait” promo picture.](https://s.yimg.com/ny/api/res/1.2/rK685gsGo0NypMCR63E_sg--/YXBwaWQ9aGlnaGxhbmRlcjt3PTcwNTtoPTk0MA--/https://s.yimg.com/uu/api/res/1.2/_NkQoZGYY1SMhOCuEWEDwA--~B/aD01ODA7dz00MzU7YXBwaWQ9eXRhY2h5b24-/https://36.media.tumblr.com/090a4a127024cf62e68561429296a025/tumblr_inline_nv7ul1cA0R1rpqds5_540.jpg)
Caitlyn Jenner poses in a long black dress for her first “I Am Cait” promo picture.
Caitlyn Jenner has let the world in on the first promo pic teasing her much-anticipated docu-series “I Am Cait” that is scheduled to premiere on July 26 on E!. The photo, shot by John White, captures the 65-year-old posing—with her hand on on hip and her back to the camera—in a long black dress with lace detailing. She completed her look with a tousled updo, diamond studs and a shimmering ring. Gorgeous!
![Caitlyn Jenner in a cheetah-print wrap dress heading into the Patricia Field store in SoHo.](https://s.yimg.com/ny/api/res/1.2/1pxpKPy8uQSndCZ1wgPxtA--/YXBwaWQ9aGlnaGxhbmRlcjt3PTk2MDtoPTE1NTE-/https://s.yimg.com/uu/api/res/1.2/NFsidNN_sZUh.o8f9GNYJg--~B/aD0yNzA0O3c9MTY3NDthcHBpZD15dGFjaHlvbg--/https://41.media.tumblr.com/c89268ddbdeabc4c3ae1c28163be61a2/tumblr_inline_nv7ul2cM871rpqds5_540.jpg)
Caitlyn Jenner in a cheetah-print wrap dress heading into the Patricia Field store in SoHo.
While in New York, Caitlyn Jenner just had to have her “Sex and the City” experience! She took some time off to do some shopping and was spotted heading to the Patricia Field store in SoHo, the store of the costume designer on the iconic show. She wore a cheetah-print wrap dress with low-slung black patent heels. Carrie Bradshaw would definitely approve!
![Caitlyn Jenner in a rainbow sequined miniskirt.](https://s.yimg.com/ny/api/res/1.2/hBBG7OPFdQi5dCIAvFfK4g--/YXBwaWQ9aGlnaGxhbmRlcjt3PTk2MDtoPTEzNjk-/https://s.yimg.com/uu/api/res/1.2/ypZ5q0dq0BbewfnAYvI4DA--~B/aD0zMDAwO3c9MjEwNDthcHBpZD15dGFjaHlvbg--/https://41.media.tumblr.com/6df8d47856920daa4667ccdd7f44f99f/tumblr_inline_nv7ul4mSWX1rpqds5_540.jpg)
Caitlyn Jenner in a rainbow sequined miniskirt.
While most people go home to rip the tags off and change into their new purchases, Jenner just couldn’t wait to get back to her hotel. At the Patricia Field store in New York City, she switched out her cheetah-print wrap dress for a rainbow sequined miniskirt and structured scuba black jacket.
![Caitlyn Jenner in Hervé Leger by Max Azria.](https://s.yimg.com/ny/api/res/1.2/9KcULL.z9fzlzCevpcY9fg--/YXBwaWQ9aGlnaGxhbmRlcjt3PTk2MDtoPTExNzU-/https://s.yimg.com/uu/api/res/1.2/eaf.J9rQ2oejUTmCQpuzYA--~B/aD0zNjczO3c9MzAwMDthcHBpZD15dGFjaHlvbg--/https://40.media.tumblr.com/f05f8048187916c6318c67f7c8735821/tumblr_inline_nv7ul53L1k1rpqds5_1280.jpg)
Caitlyn Jenner in Hervé Leger by Max Azria.
Caught! Jenner stole the Hervé Léger by Max Azria black dress she was spotted wearing out in New York City from the set of her “Vanity Fair” shoot. She paired it with low-slung black patent heels. Her hair was parted to the side and done in loose waves, with drop pearl earrings popping against her brunette coloring.
![Caitlyn Jenner in Alexander Wang.](https://s.yimg.com/ny/api/res/1.2/x6ETShLz.0yjGGJtR8WtHw--/YXBwaWQ9aGlnaGxhbmRlcjt3PTk2MDtoPTEwOTI-/https://s.yimg.com/uu/api/res/1.2/lfZiumAbEi8sNp6WXOeqbg--~B/aD02MTM7dz01Mzk7YXBwaWQ9eXRhY2h5b24-/https://40.media.tumblr.com/a52977442c608da2a955e36f3310f6ad/tumblr_inline_nv7ul8QDdQ1rpqds5_540.png)
Caitlyn Jenner in Alexander Wang.
At New York City’s PH-D Lounge at the Dream Downtown Hotel, Jenner attended a party for gay pride. She made a surprise entrance wearing a belted white T-shirt with camisole underneath, paired with a pencil skirt (Alexander Wang’s official Instagram account revealed that Jenner was wearing the Circular Hole Jacquard Midi Skirt from the T by Alexander Wang Spring 2015 collection (you can have it too for $195). Her hair was down, styled in loose waves, her lip gloss was popping, and she wore simple accessories, including a bracelet, a long chain necklace, and earrings.
![Caitlyn Jenner wearing a blush pink dress in a promo for ‘I Am Cait.’](https://s.yimg.com/ny/api/res/1.2/KumOCUAlt4C87Dxyf8S2PA--/YXBwaWQ9aGlnaGxhbmRlcjt3PTk2MDtoPTYzOA--/https://s.yimg.com/uu/api/res/1.2/gdIpaPOma9AF8_MFlIAEvg--~B/aD00MDk7dz02MTU7YXBwaWQ9eXRhY2h5b24-/https://40.media.tumblr.com/edf54b7536d21f0e96283e73e655e625/tumblr_inline_nv7ul8CItA1rpqds5_540.jpg)
Caitlyn Jenner wearing a blush pink dress in a promo for ‘I Am Cait.’
In a promo for the upcoming docuseries “I Am Cait,” Jenner was seen wearing a blush pink dress, giving off a very '70s vibe. “I’m telling my story,” Jenner says to the camera. “People don’t understand looking into the mirror and nothing seems right, putting on clothes that you just really don’t identify with. This is about getting to be who you really are.”
![Caitlyn Jenner on the cover of 'Vanity Fair.’](https://s.yimg.com/ny/api/res/1.2/_dI0Ai4.irpfelY6m6Uwrw--/YXBwaWQ9aGlnaGxhbmRlcjt3PTk2MDtoPTEzNDA-/https://s.yimg.com/uu/api/res/1.2/cyxJDMeOfsyjCYvTh_CTtQ--~B/aD05Nzc7dz03MDA7YXBwaWQ9eXRhY2h5b24-/https://41.media.tumblr.com/2998b9c521e863d196ab76a4d118aec3/tumblr_inline_nv7ul9IBHc1rpqds5_1280.jpg)
Caitlyn Jenner on the cover of 'Vanity Fair.’
While Bruce Jenner told Diane Sawyer about transitioning, Caitlyn Jenner was revealed on the cover of “Vanity Fair.” In a feature story written by Buzz Bissinger, she said, “The uncomfortableness of being me never leaves me all day long. I’m not doing this to be interesting. I’m doing this to live. … 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. You never dealt with yourself.’ And I don’t want that to happen.”
![Caitlyn Jenner in Zac Posen for 'Vanity Fair.’](https://s.yimg.com/ny/api/res/1.2/8Ljg5oW1pE9Mwabjn2piXA--/YXBwaWQ9aGlnaGxhbmRlcjt3PTk2MDtoPTgwNw--/https://s.yimg.com/uu/api/res/1.2/AjIT7R06ix8BfgniKwF3Zw--~B/aD0xMjExO3c9MTQ0MDthcHBpZD15dGFjaHlvbg--/https://41.media.tumblr.com/bec3b63cd59d976118bd61b7a1dd6ccf/tumblr_inline_nv7ul9d7s51rpqds5_1280.jpg)
Caitlyn Jenner in Zac Posen for 'Vanity Fair.’
“The pictures came out over-the-top great, you know, and I think people’s reaction when they see it, I was always worried — you never wanted to look like a guy in drag, you never wanted to look like a guy in a dress, OK,” she told “Vanity Fair” of dressing in dresses, skirts, and lingerie. “If you’re going to do that, come out, you really have to look the part. You have to look very feminine, you have to be able to, what I call my presentation is extremely important because it puts people at ease. And if you can do that, OK, people are at ease, they’re just comfortable being around you.”
![Caitlyn Jenner in 'Vanity Fair’ in a Donna Karan dress.](https://s.yimg.com/ny/api/res/1.2/TbYflNTZaAXLIdgvC1nNGg--/YXBwaWQ9aGlnaGxhbmRlcjt3PTk2MDtoPTY1Mw--/https://s.yimg.com/uu/api/res/1.2/6sZnqhTQPt9TOaHLXKPnGg--~B/aD02MDA7dz04ODI7YXBwaWQ9eXRhY2h5b24-/https://41.media.tumblr.com/0c3016c799f5cfeab1961c8147827d9d/tumblr_inline_nv7ulaON9q1rpqds5_540.jpg)
Caitlyn Jenner in 'Vanity Fair’ in a Donna Karan dress.
Jenner looked fierce in a red Donna Karan dress and tortoise cat’s-eye sunglasses. The $180,000 2011 Porsche 911 GT3 RS that she’s sitting in was a gift from Kris Jenner.
![Caitlyn Jenner relaxing in Agent Provocateur.](https://s.yimg.com/ny/api/res/1.2/hGm5ysLKpYoNWyEVu8CC2g--/YXBwaWQ9aGlnaGxhbmRlcjt3PTk2MDtoPTY0OA--/https://s.yimg.com/uu/api/res/1.2/z10fTInlLhOxalN3mmPaVA--~B/aD05NzI7dz0xNDQwO2FwcGlkPXl0YWNoeW9u/https://41.media.tumblr.com/5affbb7ac471b76331e2e15232cdd3af/tumblr_inline_nv7ulbDlss1rpqds5_540.jpg)
Caitlyn Jenner relaxing in Agent Provocateur.
“Vanity Fair” fashion and style director Jessica Diehl, who was in charge of styling Jenner for her cover story, said in an interview in the magazine, “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.”
After revealing her new self on the cover of Vanity Fair, Caitlyn Jenner already knows how to dress — really well, at that. From a trip to New York, where she treated herself to a full-on Carrie Bradshaw experience to custom Versace at the ESPYs, the reality star’s sartorial sense is on point. “Fashion police, go easy on me. I’m new at this,“ she pleaded on her first red carpet. But the ask was unnecessary: in just a few months, Jenner’s transitioned from second fiddle to the famous Kardashian family to front-and-center fashion star — watch out, world!
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