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7 fashion illustrators style Caitlyn Jenner’s new look

Author: Dottie Maguire
by Dottie Maguire
Posted: Jun 04, 2015

Caitlyn’s got curves — and style! We tapped seven of Instagram’s most beloved fashion illustrators to dream up some new looks for the hottest member of the Kardashian clan, Caitlyn Jenner. Check out their day-to-night outfit picks below:

Day: "When I think of Caitlyn, I think of the words ‘powerful’ and ‘bravery.’ For my day look, I chose an all-white Yves Saint Laurent suit accessorized with a black Givenchy bag, silver-mirrored sunglasses and a classic pair of Christian Louboutin heels."

Evening: "I chose a more extravagant-yet-simple piece. I envision her on the red carpet with a black Zuhair Murad gown and a red lip — nothing says bold and brave like a red lip. It says to me, ‘I am here and I am Caitlyn.’?"

First day look: "Caitlyn has amazing pins! I’m very jealous. With this in mind, I’ve drawn her in a really modern, chic ‘Little Black Dress’ — simple neckline with a classic cut and quite short. She has the legs. It’s an elegant and modern look for the day."

Second day look: "For this look, I have Caitlyn in a soft pale-blush pantsuit. With her new cascading locks, this is a beautiful look for spring."

Evening: "Caitlyn has an amazing figure — again, very jealous — long, lean and strong. I’ve drawn her in a striking red couture gown with cap sleeves. This is her moment, and I think she would look so striking in a really bold dramatic red for the evening. After 65 years of waiting to wear feminine clothes, Caitlyn should wear as many couture gowns as she wants."

Day: "I would describe Caitlyn’s Vanity Fair wardrobe as womanly and glam, which led me to draw Caitlyn in fur for both evening and day looks. Nothing says sophisticated, feminine and chic like a fur. For day, I put Caitlyn in a fitted white T-shirt and fitted jeans, because every woman should have those basic, feel-good staples in her closet."

Evening: "I strategically chose to draw Caitlyn in black for her evening look. I didn’t want a flashy color to take away from showcasing her epic cheekbones."

Day: "For both looks I was inspired by Caitlyn’s strong shoulders and arms. I thought they looked great in the Vanity Fair issue and I also wanted to draw attention to her small waist. Both looks are very American to me. [And] there’s nothing more American than a pair of jeans."

Evening: "The evening look reminds me of Audrey Hepburn with its classic silhouette."

Day: "I chose to dress Caitlyn Jenner in two Dior Couture looks. Raf Simons is a designer who is known for looking ahead, instead of to the past, and I feel this concept aligns perfectly with Caitlyn’s story. I love the feminine silhouette of this Dior dress, and its pink hue makes it a fresh daytime option for Caitlyn."

Evening: "Caitlyn would look stunning in this couture Dior piece, because of its elegance, texture and playful sophistication."

Day: "I chose to put Caitlyn in a style very inspired by the famous Marilyn Monroe white dress blowing over the New York subway grate. There is no doubt Caitlyn is already an icon in her own right, like Marilyn. I thought this also was appropriate, given that Monday was not only the day that Caitlyn’s Vanity Fair cover debuted to the world, but was also Marilyn’s birthday. I added a shirt collar on the halter style, as a small nod to menswear, to honor Caitlyn’s history as Bruce. The look is still timeless, easy and celebrates Caitlyn’s curves — arms proudly shown, legs for miles."

Evening: "I chose to put Caitlyn in a showstopper, red evening gown. Red, in my mind, is timeless, classic, and arguably a neutral. It will always look great. With a plunging neckline and curve-conscious silhouette, Caitlyn celebrates her femininity without being over-the-top or sensationalized. The gown, I imagine, would be covered in sparkles, as she leaves a dusting behind her wherever she goes, inspiring people to live life their way.

"If I were Caitlyn, I’d totally rock my gold medal as a red-carpet-worthy jewelry piece. I’ve shown it here as a custom-made necklace with pearls. I read recently that there is already movement for Caitlyn to give back her medals, since she is now a different gender. I hope Caitlyn not only keeps them, but wears them on a regular basis."

Day: "Caitlyn is an athlete and enjoys being active. What’s easier and more effortlessly chic than a sailor shirt? Nautical stripes are flattering and fun, and I imagine Caitlyn with a loose chignon, and perhaps little diamond or pearl studs to accent this casual ensemble."

Evening: "[Here], she gets to explore and find her personal style and have fun. I loved the Vanity Fair shoot and think Caitlyn looked elegant and polished. I imagine her at evening events in sophisticated looks — with perhaps a bit of bling here and there to accentuate her neckline."

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Author: Dottie Maguire

Dottie Maguire

Member since: Mar 05, 2015
Published articles: 117

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