As religious Instagram stalkers – it’s often how we discover our best fashion interview subjects – we’ve come to appreciate those who seem to be able to nonchalantly whip up a killer outfit without so much as a calculated though. It is, we think, the definition of innate style. Take Lucky-turned-ShopBop editor, Jenna Gottlieb. Her Instagram feed is dripping with an effortless off the shoulder BCBG top here, that perfect Rachel Comey ankle boot, not to mention that just-so Frame Denim 70s suede flares. Nobody does easy, fuss-free dressing quite like Jenna and when we arrived at her Chelsea flat, it was almost instantly obvious that her wardrobe was one we wouldn’t forget.
But it’s not just her style that got our attention – her career is equally as impressive. Fashion has long been one of those industries that can feel near impossible to penetrate, whether you want to be a writer, stylist, buyer or PR. Even here at The Lifestyle Edit, we’re inundated with emails everyday looking for intern and freelance opportunities and that’s why Jenna’s story isn’t your average industry story. Despite always being interested in fashion, admittedly, she found herself directionless after college. It was only a year after moving to Manhattan, working in a restaurant, that a friend pushed her to reach out to a publication and pursue writing. That’s how she ended up at Lucky, starting first, as a fashion closet intern, then a freelance fashion week assistant, managing the calendars of 12 different editors before assisting the magazine’s founding editor-in-chief Kim France, and later, Brandon Holley before working her way up to the magazine’s Fashion Features Editor.
Her move to ShopBop wasn’t purely coincidental. After almost seven years working in print, she felt like she owed it to herself to experience a different facet of the industry and go digital. In her newly created role at ShopBop, Jenna’s at the heart of bridging the worlds of content, commerce and technology, offering customers a seamless path from inspiration to purchase through a shoppable editorial layer that sits on top of the site’s tightly curated selection of the best in contemporary wear. It means that one day, she’s flying to L.A. rubbing shoulders (taking selfies) with Mindy Kaling on a shoot; the next day working with buyers on highlighting new and niche independent brands on their homepage. Here, she gives us the 411 on work and style.
I honestly can’t remember a time when I wasn’t interested in fashion. I grew up in Los Angeles and, from a really young age, was exposed to great boutiques, flea markets, and people with really incredible innate style. My mom is very stylish, and I’d accompany her on trips to spots like the Rosebowl Flea Market, Maxfield’s or Ron Herman. As a kid, I was really tiny for my age, and I would get so frustrated that I couldn’t find clothes that appealed to me in my size. I really hated kids clothing. Finding something to wear to my own bat mitzvah was an ordeal. I finally bought a tiny little sequined-embellished slip dress that was super on sale from a store called Madison in Brentwood, where my mom often shopped. I was 12 years old, and I think had to take the straps up probably 10 inches. But I’ve always loved the thrill of the hunt, and dressing differently—I still love finding and wearing things that no one else has.
Growing up, Vogue was kind of the holy grail of fashion magazines, but discovering Lucky as a teenager was like when you make a new friend who you become instantly obsessed with. It just felt comfortable, and very me. The clothes, the voice, the discovery—it represented everything I loved about fashion. I went to Washington University in St. Louis where I majored in English and Film & Media Studies (it was my own made-up way of studying journalism, which wasn’t offered as a concentration), but found myself pretty directionless after college. I wanted to be a writer, and had always loved fashion, but I hadn’t identified a career path, or even an industry, that really grabbed me. After moving to Manhattan and working at a restaurant for a year, I finally decided I wanted to work in magazines. At the time, a friend from school was designing for a clothing label and had a lot of contacts at different titles. She said, pick one and I’ll reach out. I immediately thought of Lucky.
I started as an intern in the fashion closet, which was a true mash up of hard work and amazing insight into how a fashion magazine works. After my internship ended, I was asked by one of the editors to come back and work as a freelance fashion week assistant, which meant I handled scheduling the fashion week calendar for roughly 12 different editors. The hours were insane (this was pre-online invites and fashion GPS), but I loved every single second. It was such a lucky opportunity, because I was granted access to practically everyone in the fashion department, from the market editors to the creative director and editor in chief. It was that short-term role that led to a permanent position as the assistant to Kim France, Lucky’s founding editor in chief. Kim was amazing, because, as a former music journalist, she was sort of this unlikely fashion editor. You could tell that Lucky’s inclusive attitude about fashion really started with Kim. I always wished that I had gotten to write for her. Brandon Holly, who succeeded Kim as editor in chief, kept me on as her assistant. She also gave me my first opportunity to write professionally, for Lucky’s website, which ultimately led to a features editor position on the print side.
As Associate Editor, I was responsible for writing recurring features, such as Lucky Girl and the City Guides. The City Guides were the most fun—I would travel to a different destination each month (Austin! Oahu! Aspen!), research the best the city had to offer in terms of shopping, and write a comprehensive guide for our reader. Those trips were some of the most memorable of my life, because in those instances, I would totally hit the ground running, visit as many spots as humanly possible, and meet up with anyone I had a semblance of a relationship with (my friend Megan’s boyfriend’s mom in Nashville? Sure!) in order to learn as much as I could about where I was. The experiences taught me how to travel in a way I never had before. My last position at Lucky was as the Fashion Features Editor, where I oversaw the front of book section, and wrote a bulk of the magazine’s fashion copy, including the occasional cover story. That role is very special to me, because it represents a time where I felt that I had finally matured as an editor and was comfortable trusting my own gut and voice. And I got to work for Eva Chen, who is all of the things I really want to be: incredibly kind, incredibly professional, and someone with perfect, cool hair.
By far, my favourite aspect of being at Lucky was the people. I worked with some of the nicest, smartest, most stylish, hilarious, silliest women (and a few dudes!) who just made the environment feel very one of a kind. They’re people I still see regularly and consider some of my closest friends. I came into print at a very interesting time, when a lot of people at Condé Nast, Lucky’s parent company, referenced the golden olden days. Change and experimentation were absolutely in the air, but I always felt like the integrity of the brands remained priority one, and that’s something really unique to the industry.
My job as an editor was about spotting new discoveries—an electrifying young designer, an eye-catching micro trend, an up-and-coming tastemaker—and packaging those finds in ways that were interesting and compelling for our reader. In print there’s a sense that what you create is both of-the-moment and permanent—it’s definitive after a certain point. So the content is considered in ways that digital features aren’t always. I love the collaborative nature of print—how every story is touched by fashion editors, photo researchers, copy editors, fact checkers, and designers. It’s a team effort in this really unique and almost precious way.
I had been working in print for nearly 7 years, and felt like I owed it to myself to experience a different facet of the fashion industry. I wanted to learn new skills, and I wanted to do something in the digital space and on the brand side of things. Shopbop checked all of the boxes. And I felt about Shopbop the way I had about Lucky—that the brand was accessible and fun, but super smart and really personally right for me.
I’m the Features Editor at Shopbop, which is a new role for the company. I oversee all of the editorial copy for the site—everything from homepage features to emails—and work with various departments across the board, from the fashion and styling teams to the marketing and traffic groups, to creatively concept our daily stories and work on large-scale projects. I collaborate on everything from homepage features, to celebrity style muse stories, to bigger initiatives, like our holiday campaign. I also contribute to our men’s site, East Dane, where I’m helping develop our editorial point of view.
My print background is definitely an asset, because I think it gave me a unique understanding of how to editorialize concepts, and inject trends and ideas with colour and personality. At a magazine, you spend a ton of time brainstorming, and I’m getting to do a lot of that at Shopbop, which has a very innovative, synergistic mentality. We’re very encouraged to bring any and all ideas forward.
My last position at Lucky was as the Fashion Features Editor, where I oversaw the front of book section, and wrote a bulk of the magazine’s fashion copy, including the occasional cover story. That role is very special to me, because it represents a time where I felt that I had finally matured as an editor and was comfortable trusting my own gut and voice. And I got to work for Eva Chen, who is all of the things I really want to be: incredibly kind, incredibly professional, and someone with perfect, cool hair.
A lot of what has changed is my mindset. At Shopbop, we create content, which spotlights our product, which the customer is (hopefully!) inspired to buy. You gauge when, and which types of, stories are successful. And you really learn to put the customer first. In some ways, it’s so much more satisfying, because you’re not just sending your efforts out into the ether with zero sense of return. It’s so cool to now be able to measure both emotional and monetary success in terms of clicks and sales. I love when something we’ve consciously chosen to feature sells out. It’s such a tangible way of understanding levels of engagement and excitement. I will always think that print is so glamorous though. And, as a writer, I admire how some of the greatest talents still use magazines as their most expressive forums. The magazine world—and the fashion magazine world in particular—is such a fun, weird little club, and sometimes I definitely miss it. Other times, not as much.
In terms of product, Shopbop has such an incredible selection. There really is so much stuff. And while the vast variety can be daunting, the amazing thing is that there truly is something for everyone. I want the editorial content to help guide the shopper. I want it to function as a tool that will lead her to discover a great pair of jeans, learn about an up-and-coming designer, or sample a new colour or silhouette. The content is really there to serve our customer, and that informs our unique perspective, which is to always try and provide a takeaway for our shopper, whether that be in the form of a style tip, or a fisherman knit she’ll order and absolutely live in.
Priority A-one for me is to keep the Shopbop voice engaging and colloquial. I really try to avoid using tired or rote fashion language—it’s amazing what your brain will come up with when you restrict yourself from using words like ‘cool’ or ‘chic.’ Lucky taught me to avoid word repetitions like the plague, and that’s still something I abide by. It’s kind of a game—I’ll think, the word ‘sophisticated’ has been creeping into a lot of my stuff. So I’ll add it to my personal ‘endangered words’ list, which reminds me to use it extra sparingly. I read a ton, and look to unexpected places for language and voice inspiration, like a food magazine, lifestyle site, or a start-up’s branding.
In terms of generating ideas, I always try to keep my eyes open. We debut a new story every day, and it’s a fun challenge to think of different ways to present recurring concepts. It definitely helps when you have a trove of inspiration to pull from. A few of us on the creative team keep a list going of ideas—everything from pie-in-the-sky concepts, to ideas for lifestyle features, to lists of crazy-stylish people you’ve never heard of but who we’d love to feature in some form when the time is right. Again, it’s really about the customer. And it helps that so many of my friends are real women with great fashion sensibilities—they are the Shopbop customer! I think of them, what they would want to see, and what type of content would inspire them to make a purchase. My friend Robyn is a lawyer, and she always complains that workwear features are complete bullshit, because they never actually spotlight pieces she could realistically wear to the office. So I’ll take something like that and think, let’s do a workwear story that passes the Robyn test!
We recently began highlighting some of our more niche and independent brands on our homepage in a section called Designer Spotlight. It allows us to shout about some of the smaller, lesser-known names that we at Shopbop feel passionate about—brands like Cover swimwear or the cult-favourite line Apiece Apart. We also regularly produce a “Names to Know” feature, which is a portfolio of our favourite emerging brands. The last roundup included designers like Dodo Bar Or and Greek label Zeus + Dion, along with a fun little bio about each one. I love stories like that because they’re at the intersection of feature writing and retail—that’s kind of my sweet spot. And the payoff is huge for the customer. What’s better than learning about a new label and then instantly filling your cart with its latest designs?
A lot of what has changed is my mindset. At Shopbop, we create content, which spotlights our product, which the customer is (hopefully!) inspired to buy. You gauge when, and which types of, stories are successful. And you really learn to put the customer first. In some ways, it’s so much more satisfying, because you’re not just sending your efforts out into the ether with zero sense of return. It’s so cool to now be able to measure both emotional and monetary success in terms of clicks and sales. I love when something we’ve consciously chosen to feature sells out. It’s such a tangible way of understanding levels of engagement and excitement.
I’d say that everyone on the creative team actively thinks about our social platforms in the brand sense. The stylists, buyers, market editor, and I all regularly send pictures to the social team for use on Instagram, especially when we’re out and about at fashion week or in market, or on set. There isn’t any pressure when it comes to our individual feeds. However, when I’m excited about a story I’ve worked on, I’m 100% going to post about it. Last year I was on set in L.A. for our shoot with Mindy Kaling—she was appearing in a story we do called Style Muse. I established two equally important goals for the day: 1) become Mindy’s best friend, 2) Get a picture with her for my Instagram. I was 50% successful.
I don’t ever want to be one of those iPhone zombies who walks into people on the sidewalk or falls through a manhole while I’m checking Snapchat. But I’m definitely not always great at putting my phone down. My strategy is forced separation. My favourite thing to do when I get home from work is to leave my phone in the bedroom and forget about it for a few hours. And nothing ever important happens! When I finally do check it later in the night, all I have is a missed call from my mom and a text from the dentist’s office reminding me that I need a cleaning.
Digital has been hugely revolutionary in fashion in that it’s affected how people shop, and how they learn about what they want. Those are things I’ve known for a while, but being at Shopbop has really solidified my understanding. The “want it now” mentality is really, really a thing, and it doesn’t stop with fashion—the same goes for food, news, everything. In fashion, you can see that need for instant gratification most recently on last season’s runways, in the form of shoppable shows from Rebecca Minkoff and Burberry. The industry feels constantly in flux—like there’s always something new right around the corner waiting to pop out. I think the evolution and advancements are fascinating.
At Shopbop, I feel much more a part of a business than I ever did as a print editor. I love that I’ve been able to work with myriad teams across the board—from UX designers to marketing directors to buyers to email specialists. We’re all striving towards this common goal of customer satisfaction and growth, and that has been hugely educational. It’s a lot of spreadsheets and data, but my brain kind of loves that. And the onslaught of information helps to put everything I do into a really meaningful context. I also love that I know who our customer is—the countries she lives in, what she buys—and that is so evocative and helpful when it comes to creating compelling content. Shopbop is a global brand, and that’s been very eye-opening for me as well. The scope is just larger—there are more eyeballs on what I write now than ever before.
My personal style is a little bit nineties, a little bit streamlined, and kinda boyish. I love nothing more than a turtleneck, trousers, loafers, and eyeglasses that take up half my face. But I also love the gen-x look of mid-rise jeans with a crewneck tee. I wouldn’t say I have a uniform, but when it comes to the day-to-day it’s generally a mix of the following fairly classic/bordering-on-boring pieces: soft, hefty sweaters, button-downs, tweedy blazers, vintagey jeans, a great leather jacket, and some sort of casual shoe—like a white sneaker, Chelsea boot, or slide. I like to sneak in a feminine detail, like a drapey blouse or ultra-high waistline. I love denim everything—jackets, skirts, dresses, shirts, cut-offs—and have recently been living in a pair of Orange Tab Levi’s that I snipped at the hems. I don’t necessarily shy away from trends, but I’m selective. I get excited when I add a new silhouette into the rotation. It’s like giving your wardrobe a Red Bull.
It’s probably not shocking that since starting at Shopbop, a vast majority of my clothing comes from the site. I love Rachel Comey and Apiece Apart for unexpected basics, Jenni Kayne for everyday flats and Rochas for exquisite, black-tie appropriate ones. Derek Lam 10 Crosby and Wes Gordon for versatile designs that also make me feel like a grownup, Suno for special-feeling pieces, and Nili Lotan slip dresses for fancy occasions. I love Veda leather jackets, and delicate, playful jewelry from Jennifer Zeuner and Aurelie Bidermann. Ulla Johnson designs perfect tunics. ATM tees are a joke they’re so soft. I’m really into all of the simple, ‘70s-style cuts Frame is doing right now, and am loving Citizens of Humanity jeans—the slouchy, straight-leg Liya is so, so good.
There are a lot of exciting new/newish brands on the site! Some have already generated buzz of course: Paul Andrew, who makes beautiful shoes, is one. He’s already sort of a fashion darling, but his stuff really is so pretty. Sandy Liang makes the most fantastically fluffy yet somehow tough outerwear. Warm, a beachy collection started by the same-named New York boutique, is like Tulum in clothing form. Saylor is an adorable line of rompers and little dresses. Goen.J. makes these sculptural, almost cerebral pieces. Jacquemes is just so original. I always look forward to their latest because it’s consistently a little bit wacky but completely wearable. Ganni is a Scandinavian label that’s been around for a while, but I love their modern, feminine pieces. It’s a great name to know.
I’ve definitely become a smarter shopper, and I think that’s led to my wardrobe being a bit more refined and considered. For a long time, I was almost too experimental and impulsive, and I ended up wearing some really unflattering or straight-up batshit things. Now, I really think about something before I buy it. It’s become way more controlled. My former co-worker and dear friend Jayna Maleri taught me that before you buy something, think of three different ways to wear it. It’s a very, very good rule for keeping impulsivity at bay.
There are a couple people who have made a big impression on my style. The first is my mom, who as I mentioned before, has a great sense of style. She always encouraged me to dress for myself, and enabled my love of clothing and style. Growing up, I’d go on these weird quests, where I’d NEED to have something, like a Keroppi ring watch or ‘50s vintage carpet coat, and she’d make it her quest too. She never chastised me for caring about what I wore, or being picky about my wardrobe. She also taught me the importance of looking pulled together, though admittedly that took longer than it probably should have. But I’ve gotten a lot better about doing things like replacing certain staples when they’ve basically disintegrated, and being diligent about going to the tailor when a fit needs to be tweaked—it truly makes me feel like a more sane, together person. And that’s something I’ve gotten from my mom, who, to this day, will be the first one to tell me when I need to tweeze my eyebrows or colour my hair or throw out an article of clothing that has one too many holes in it. The second person is Alexa Chung. Yep, her. She’s sort of the style crush who I can’t ever seem to move on from. There are days when I’ll feel iffy about my outfit before leaving the house and I’ll ask myself, “Would Alexa wear oxfords instead of Supergas with this?” It’s an oddly effective decision making strategy.
My mom always encouraged me to dress for myself, and enabled my love of clothing and style. Growing up, I’d go on these weird quests, where I’d NEED to have something, like a Keroppi ring watch or ‘50s vintage carpet coat, and she’d make it her quest too. She never chastised me for caring about what I wore, or being picky about my wardrobe.
Trends-wise, obviously, I’m totally on board with pyjama dressing. The shirt I’m wearing now is an oldie but a goodie. I’m not a very fussy dresser—I don’t take a lot of time to get ready in the morning—and I love how the look is easy and luxe, but not at all messy. I’m also enjoying the resurgence of quirkiness. I’ve always been a fan of designers like Miuccia Prada, Dries Van Noten, and now Alessandro Michelle at Gucci—people whose approach to fashion feels at once thoughtful and irreverent. It’s funny when then that out-of-the-box aesthetic becomes mainstream.
The most cherished item in my wardrobe is probably my watch, which was a birthday gift from a few years back. I wear it every single day and am now one of those annoying people who’s like, ‘I feel naked without my watch!’ I also have a few sleep shirts that I will never ever part with (my best friend gave me a Broad City tee with illustrations of Abbi and Ilana’s hair over the boobs). And one particular pair of vintage Levi’s (they’re probably from the ‘80s) that I ordered off of Ebay on a whim, and that magically fit perfectly. I’m really pretty proud of those guys.
I love great tailoring. A pant with a sharp pleat or blazer with crisp, clean lines always seems to catch my eye. I really like a blocky, modular silhouette, though my boyfriend tells me I look like a Lego when I wear really boxy things (it’s annoyingly accurate). I don’t wear a ton of black, but I do really love navy, gray and white—a great white top is a weakness. I love prints, but am really really picky about patterns. I don’t like anything too abstract or geometric, or overly sweet. It’s more of an, ‘I know it when I see it’ kind of thing. Oh and stripes! I’ve had to put the kibosh on items I found myself overbuying, and striped tees are at the top of that list. Gray sweatshirts are on there too, as are Chelsea boots.
Naturally, I’m a big online shopper but my friends’ boutique Concrete + Water in Williamsburg has a perfectly curated selection of independent and contemporary designers, as well as inspiring home stuff. In Soho, I love the Rachel Comey store and Trademark, which are both beautiful shops where you can see an entire collection in full. I love Warm in Nolita for beachy odds and ends. French Garment Cleaners in Fort Greene is great for classic, beautifully made staples. And Barneys is always a very fun one in New York.
For downtime, I read a lot! Mostly contemporary fiction. I joke that my Kindle is my best friend, and I always have it with me. I go for runs on the West Side Highway a couple of mornings during the week, and on the weekends. It’s my favorite form of exercise. That and classes at Yoga Vida. In the fall and winter, I spend too much time watching football. I was born in Chicago and am a Bears fan, which is sadly not always easy. I see a ton of movies. I love a good podcast, and I listen to a lot of Howard Stern, who is the best interviewer of all time. Though I don’t go nearly enough, concerts makes me so so happy—especially when they’re at magical venues like The Beacon, Jones Beach, Bowery Ballroom, or Radio City. And I bake! Especially when I’m feeling stressed. It’s so calming. I also love to eat. My boyfriend and I go to Bar Sardine in the West Village often. We’ll sit at the bar and order burgers, which are arguably the best in the city. And in the summer they have a drink called ‘What’s Your Favorite John Hughes Movie?’ which is the very best name for a cocktail. I love Russ & Daughters café for breakfast. You have to go crazy-early to avoid waits, but it’s so worth it. Roberta’s in Bushwick is the ultimate hipster destination, and the pizza is so good. And St. Anselm in Williamsburg is always a delicious, indulgent night. I also really love getting out of New York, so traveling is a big priority. We went on a big trip to Japan last summer, which was magical. And right now we’re planning a week in Greece for a friend’s wedding.