Dylan Penn

Unlike some Hollywood entitled progeny, twenty four year old Dylan Penn’s inherited the best of her parents’ DNA: silky Breck-girl blonde hair, a sculpted face, a slender but curvy body (the Robin Wright part); with the unlikely combo of depth, smarts, determination and talent (the Sean Penn and Robin Wright part) - plus a heavy dose of unpretentiousness/healthy skepticism about Hollywood and show business (yes, the other Penn part).

  • Photography: Justin Campbell
  • Writer: Lily Bart
  • Editor: David Niederhoffer
  • Stylist: Monty Jackson
  • Makeup: Ashleigh Louer
  • Hair: Derek Yuen
  • D. Penn Agency: DT Model MGMT
Dylan Penn with a d
-Dylan Penn | Photographed by Justin Campbell

Portrait of Dylan Penn standing and showing skin in a crop top

Fashion Credits

Styled By: Monty Jackson

Looks 1 & 4
Look 2
Look 3
Look 5

Dylan and her younger brother Hopper were brought up in Ross, a town in Marin County where she attended the Marin Academy – a far cry from Hollywood’s competitive class conscious Brentwood school or Crossroads. Having grown up imagining she’d wind up unselfconsciously behind the camera – most likely as a screenwriter – Dylan’s suddenly emerged – to her own great surprise - as a budding Hollywood hyphenate model/actress, with a Gap campaign in 2013, appearances in GQ, W and Ellen – then more recently, a Vogue shoot with photographer Mario Testino, a campaign for Florentine house Ermanno Scervino, a Stuart Weitzman campaign shot by Julia Restoin Roitfeld – that featured Dylan without pants accompanied by Poppy Delevingne, and an array of flirtatious ads with Bonds Lacies, an Australian relatively demure sweet lingerie brand. The pics are a little bit cheesecake – but in an innocent 1950’s sort of way. However, that was not the case when she posed nude for the magazine treats! in 2014 – though she was partially obscured by a Fendi bag. Her reasoning? She wanted to shoot with photographer Tony Duran, because she’s an admirer of his nude black and whites.

Her foray in acting began when she appeared in the Nick Jonas video for the song "Chains" – then took her first role in the horror film The Condemned, about squatters who are haunted by decrepit tenants. “I’m not a fan of horror movies,” she admits. “But I really admire writer/director Ely Morgan Gessner and felt comfortable with him.”

Dylan Penn close-up portrait with wavy hair

Then she took another small part in the upcoming Elvis and Nixon – with her mom’s co-star Kevin Spacey. “It’s funny it should be with Kevin Spacey, because of House of Cards – but I didn’t shoot with him on Elvis and Nixon (he’s Nixon to Michael Shannon’s Elvis) and barely saw him.” Her image may be one of youth and beauty – but behind those doe eyes, there’s also a serious cerebral streak. And nothing superficial. While growing up in Northern Cal, she was purposely insulated from the entertainment biz and fashion – so her style icon was somebody with moxie and street chic: “The only girl I ever wanted to dress like was Gwen Stefani,” laughs Dylan. “I started wearing my brother’s CK underwear over my jeans. I thought it was cool because she did it – thinking back, I was probably a little too young for that.” She’d never even been to a fashion show before her mother took her to Paris for January’s Chanel couture show by special invitation from Karl Lagerfeld himself. “I’d never been to a fashion show,” she admits, a little wide eyed. She got to don a navy blue Chanel dress with Chanel black low heeled shoes. “It was amazing,” she says. "I’m not a huge fashion advocate – but now I really think of it as an art form.”

Dylan Penn sexy black and white portrait

JJ: So do you enjoy modeling?

DP: Honestly, I hate posing for photos- it’s not something I enjoy doing- but you’ve got to make a job look good. It's not something I feel comfortable doing. But I have had a blast so far and I am lucky to get to work with major people in fashion!

JJ: What do your parents think of all this?

DP: My parents never discouraged me from doing anything. Both my parents have been very supportive – but let me have my own independent path. They’re just happy I’m busy. I think it was a huge advantage growing up outside of L.A. Especially because my parents are in the industry; being the child of someone famous can be a strange lifestyle – but I had a really normal childhood, which I don’t think I would have really had here.

JJ: Do you think that it was an advantage growing up outside of L.A.?

DP: It was a huge advantage. Because my parents are in the industry, growing up in L.A. would’ve been really odd. It’s a really strange lifestyle being the child of someone who is well-known. Growing up outside of it, I had a really normal childhood, which I don’t think I would have had here.

JJ: What’s your relationship with your younger brother Hopper like?

DP: My brother and I are really close - even though we couldn’t be more different. He’s always been the entertainer – and I’m more shy - and I’m not funny! He was always the athlete, I’m into the arts. But what really brought us together is we’re passionate about a lot of the same things: how loyal we are, how intimate our relationships with our friends.

JJ: What did you think of your mother’s recent Vanity Fair cover?

DP: She didn’t tell me till after the fact. She was so nonchalant; I don’t even think she said it was the cover. A friend of mine sent me the photo of the cover, then I went to the newsstand. I know how beautiful my mom is, so to see is so great.

JJ: What’s your favorite of your dad’s movies?

DP: It’s hard to say, because I haven’t seen all of them. I love Dead Man Walking, he was so fabulous in that movie - he transforms for sure. But he doesn’t talk about how. Growing up, he never really talked about it. He never brought work home in that way. He kept it very separate.

JJ: What do you do in your free time?

DP: In my free time, I just like being outside. Living in L.A., obviously we get to take advantage of that every day. I love going hiking or just hanging out with friends. I go to the movies constantly. And I write in my free time. I write about my family or things that are really close to me. I have a thing that every time after a family trip or a holiday, I always write either a short story or a short film based on that experience. The last trip I went on, I went skiing in Whistler with my family and I wrote a short story about that, just to keep it going. I know that if I stop I feel like I’ll lose something.

Dylan Penn sitting down for a portrait
JJ: Do you still have aspirations to be a writer?

DP: I have a huge passion for writing and it’s my dream to direct something of my own. But right now, I’m learning so much in front of the screen; it’s really going to help me later.

JJ: So what’s next with your acting career?

DP: I haven’t taken any classes for acting. I kind of accidentally fell into it and I just have a lot of fun doing it. If I really want to pursue it, maybe I will take a class or get coached to be more professional or have a better skill set. For now, I like taking it very slowly and whatever comes, comes.

JJ: Growing up in a family of celebrities, did you ever have a celebrity crush?

DP: No, I don’t think I have a celebrity crush. I tend to like people who are out of the limelight. It’s just not something that I’m really attracted to.

Behind The Scenes: Beauty Feature

Makeup artist Ashleigh Louer wanted to create a sultry, glowing, and beautiful makeup look on Dylan for this shoot. Perfect skin was her focus and she started by prepping with Avene Thermal Spring Water mist and mixed Embryolisse moisturizer with Dior Pro Youth Sorbet essence serum. She also prepped the eyes with Kate Somerville Line Release eye repair cream. Next, she mixed a little Charlotte Tilbury Wonderglow primer with Laura Mercier’s Radiance primer to make the base extra bright and glowy.

Dylan Penn Behind The Scenes getting her hair done

Dylan Penn Behind THe Scenes getting her makeup done

Dylan Penn Behind The Scenes getting lipstick applied

Ashleigh then applied Laura Mercier Tinted Moisturizer in “nude” with a beauty blender sponge and used Laura Mercier Secret Camouflage in #3 to areas that needed more coverage. To set the makeup, she then used the same brand’s Loose Mineral Powder in “real sand” to keep the skin looking luminous instead of dry or matte. To warm up Dylan’s complexion, she used Nars blush in “madly” and then added Nars Douceur to the cheeks. To complete the look on the skin, Tom Ford’s Shade & Illuminate duo was used. Since it’s a cream, it was used last to highlight certain areas.

Dylan Penn Behind The Scenes getting makeup applied to lips

For the rest of Dylan’s makeup look, Ashleigh shaped her brows with Sephora’s Retractable Waterproof Brow Liner in “honey blonde,” brushed the brows in place, and then set them with a clear brow gel. She used a few eyeshadow colors from Laura Mercier - “stellar” for all over and inside the corner of the eye and then “cafe au lait” and “fresco” in the crease and around the eye. These shadows were used to blend out the Eyeko Shadow Eyeliner combo in “chocolate” and “taupe.” Next, MAC Fluidline eye liner was pressed into the lashline and a slight cat-eye liner shape was added as well. She pressed a little of the Tom Ford highlighter used earlier onto the eyelids for a final pop of shine. After curling the lashes, Benefit’s They’re Real! mascara was applied and Ardell individual flare lashes in medium were used to add a little drama.

Because Dylan has the most amazing lips, Ashleigh decided to keep them neutral by using Dior Addict Lipstick in #222 with a bit of Kevyn Aucoin lip gloss in “dahliana.” The final step was body glow and equal amounts of Prtty Peaushun in light and Elizabeth Arden’s Eight Hour Cream were mixed to really make the skin shine.

Dylan Penn Behind The Scenes getting her hair done

Dylan Penn Behind The Scenes getting blush on her cheeks

The look that hair stylist Derek Yuen set out to create for Dylan was a classic blowout with some soft waves. He wanted her to have maximum shine to show off how full and healthy her natural hair is. To create this, he started by using Bumble and Bumble Prep from the roots to ends and layered Bumble and Bumble Thickening Spray generously on top of that. He blow dried each section of her hair and set into hot rollers. Once it was set in, it was important to let it cool down for at least 15 minutes to ensure the blowout lasted all day.

To finish, Derek brushed all the hair together using a little bit of the Bumble and Bumble Spray de Mode to give it a brushable, touchable hold. Then, using a large curling iron in certain areas, mainly around the front, to give it a slightly deeper wave and give the hair a bouncier feel.

Dylan Penn Behind the Scenes getting work from hair and makeup


  • Photographer: Justin Campbell
  • Photo Assistant: Chris Moneberg
  • Stylist: Monty Jackson
  • Hair Stylist: Derek Yuen
  • Makeup Artist: Ashleigh Louer
  • Writer: Lily Bart
  • Editor: David Niederhoffer
  • Web Producer: Chris Choi


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