We recently connected with JenniLee and have shared our conversation below.

JenniLee, appreciate you joining us today. Can you talk to us about a risk you’ve taken – walk us through the story?

You know, my biggest risk was probably deciding to step out from behind the scenes and build my own business. I’d spent over 20 years styling celebrities—Lauryn Hill, Greta Gerwig, Scarlett Johansson—always being the invisible person, making everyone else look amazing. I’m actually quite introverted and got into styling because it was specifically behind the camera.

At the time, I had one personal styling client who kept telling me that there were many women just like her who needed my help. But I had resisted shifting my focus, until the pandemic hit, and suddenly there were no music videos, red carpets, or magazine shoots. All these female entrepreneurs showing up on screens, building businesses, and many were struggling with the exact thing I’d been helping celebrities with – how to look confident through their clothes.

But here’s the thing – becoming the face of my own business meant doing everything I’d avoided my whole career. Getting on camera, building a personal brand, and showing up on social media. I was basically betting my entire career on my ability to go from invisible expert to visible authority.

My camera shyness and introversion actually became my superpower. When I talked about using clothes as confidence armor, it wasn’t just styling advice – it was deeply personal because I lived it every time I had to show up on-screen. That vulnerability made me so much more relatable to other entrepreneurs dealing with the same visibility struggles.

Now I’m quoted in magazines like Glamour and Real Simple, I’ve built a business helping female entrepreneurs align their style with their goals, and I’ve proven my expertise translates way beyond celebrity styling. The biggest win was discovering that being a stylist could be a purpose-driven career that changes lives.

JenniLee, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?

I’m JenniLee, a fashion stylist and image consultant based in NYC who helps ambitious, creative female entrepreneurs transform their relationship with their wardrobes through my “more styling, less shopping” approach – creating powerful looks from what they already own while making only strategic additions.

I got into styling almost by accident. Growing up, my Nana Kitty was my style icon; she taught me that “making an outfit can make your day.” When I moved to NYC in my twenties, while working in costume departments on indie films, a celebrity stylist spotted my personal style and hired me. This launched me into a 20+ year career of styling A-list talent—from Angelina Jolie to Rashida Jones—for major campaigns, world tours, magazine covers, and red carpets, including launching the magazine ANTENNA and serving as fashion director.

The core problem I solve is style paralysis, specifically for successful women with closets full of clothes but who continually feel as if they have nothing that works. My clients struggle to translate their professional identities into confident visual presence. They’re spending money on pieces that don’t work together, feeling underdressed for networking events, or avoiding opportunities because they don’t feel put-together enough.

What sets me apart is my editorial background. Most personal stylists come from a retail background; they’re trained to sell clothes. I come from celebrity and editorial styling, where my job was selling dreams and aspirations to audiences. When working with clients, I’m not pushing products; I’m creating visual stories that communicate who they are and where they’re going. I know how to help them project authority, creativity, or approachability because I’ve spent decades crafting those narratives for magazine covers and red carpets.

This background also uniquely equips me to guide clients toward sustainable consumption. In fashion shoots, we constantly created multiple looks with a single piece; that’s where I learned to reimagine and restyle existing items in countless ways. Now I teach clients these techniques, helping them reduce overconsumption by discovering new styling possibilities within their current wardrobes. The “more styling, less shopping” way.

My services range from the intimate Style Club group membership and comprehensive 1:1 Bespoke programs to virtual styling sessions, in-person house calls, and shopping trips. I’m particularly proud of my signature SPARK framework that helps women identify their authentic style while ensuring it serves their professional goals every single day.

What I want people to understand is that investing in your image isn’t vanity—it’s a strategic move. When you feel confident in what you’re wearing, you speak with more authority, take up space differently, and stay present instead of self-conscious. That confidence impacts everything from client relationships to revenue. My approach isn’t about following trends or spending tons of money; it’s about understanding what works for your body, lifestyle, and goals.

The transformations I witness go beyond wardrobes. When a client tells me she nailed a major presentation because she felt completely confident in her outfit, or that she’s stopped buying clothes she never wears, that’s everything to me. I’ve been quoted in Glamour, Real Simple, and The Zoe Report, but individual success stories matter more than press.

Ultimately, every woman deserves to feel as powerful on the outside as she does on the inside, and my job is making that transformation effortless.

Any insights you can share with us about how you built up your social media presence?

My social media journey was forced by necessity. Before I pivoted to being the face of my own business, my Instagram was basically a styling portfolio mixed with fashion inspiration – lots of behind-the-scenes shots from shoots, trend spotting, maybe some vintage editorial. My stories were mostly about my cats or flowers and sunsets. I was rarely on screen myself because, honestly, I preferred being off camera.

When the pandemic hit and I had to start building my own brand, I realized I couldn’t hide behind other people’s photos anymore. I had to actually show up as myself, which was terrifying for someone who’d spent 20+ years being the person behind the camera.

What really worked was leaning into authenticity instead of trying to be polished, and this was not easy for a perfectionist and editorial stylist. I started by sharing my own relationship with the clothes in my closet: why I held onto things I no longer wore, or how to style pieces in multiple ways. Those vulnerable moments got way more engagement than any perfectly curated styling shot ever did.

I also used my celebrity styling background strategically—not to name-drop, but to teach practical lessons. When I told the story of crashing SNL after-parties so I could tell Michael Stipe that he was wearing a shirt I had bedazzled 24 hours prior, I was able to summon the chutzpah because of the outfit I wore. It became a lesson about having signature pieces that give you confidence in any context.

Building real relationships became crucial. I started actively engaging with my followers – DMing people who shared their style struggles, commenting genuinely on their posts, and responding to their stories. Some of my best clients actually came from those authentic Instagram conversations. I treated social media like actual networking, not just broadcasting.

For anyone starting out, my biggest advice is to focus on being helpful before being perfect. Share your expertise generously, show your learning process, including mistakes, and consistently solve real problems. But don’t just post and disappear; actually engage with people who comment or DM you. Your audience doesn’t need to be huge; it needs to be engaged and actually care about what you offer.

The hardest part was getting comfortable being visible, but once I started sharing authentically about that struggle, it became my superpower. Turns out other entrepreneurs were dealing with the exact same visibility anxiety I was. Getting used to talking on camera takes time, and it’s okay if it doesn’t come naturally. I still feel awkward doing it!

Any thoughts, advice, or strategies you can share for fostering brand loyalty?

I keep in touch with clients primarily through my weekly newsletter, which has become the heart of my community. It’s not just marketing; I genuinely treat it like writing to friends. I share personal stories, behind-the-scenes moments from my styling work, trend insights, and client transformations. People tell me they look forward to Tuesdays when it hits their inbox, which means everything to me.

Many people discover me through my free style quiz that I promote on Instagram. It’s designed to help women identify their style personality, and once they take it, they are added to my newsletter list. This attracts potential clients who are genuinely interested in style guidance, while also providing them with immediate value. The quiz results provide personalized insights that they can use right away, and the newsletter keeps us connected.

I regularly share curated shopping links focused on resale items from The RealReal, especially trend-driven pieces that align with my “more styling, less shopping” philosophy. This way, if someone wants to try a new trend without the full retail investment, they can find quality pieces at better price points while being more sustainable.

What fosters loyalty is having multiple ways for clients to continue working with me at different levels. Someone might start with a virtual styling session, then join Style Club for ongoing support, and eventually invest in my Bespoke program for complete transformation. Alternatively, they might start with an in-person house call and later join Style Club to sustain their momentum within a community of like-minded women.

This structure enables me to support clients wherever they are in their style journey and budget. A client might use my services intensively during a career transition, then stay connected through Style Club for ongoing weekly group styling sessions and seasonal updates. It’s not about constantly upselling; it’s about having the right support available when they need it.

I also stay engaged through social media, responding personally to DMs and comments. Some of my best long-term client relationships started as casual Instagram conversations. I make it easy for people to reach out when they have questions or want to share their style wins.

The key is genuinely caring about their continued success. When a former client sends me a photo of herself looking confident at a big presentation, wearing pieces we styled together months ago, that’s what brand loyalty looks like. It’s not just about the transaction; it’s about being part of their ongoing confidence and success story.

Contact Info:

• Website: https://www.jennileestylist.consulting/
• Instagram: https://www.instagram.com/jennileestylist
• Linkedin: https://www.linkedin.com/in/jennileestylist/
• Other: https://www.jennileestylist.consulting/quiz

  https://shopmy.us/jennileestylist

  https://www.jennileestylist.com

Image Credits

Editorial images for Flaunt Magazine shot by Sharum + Ari, Editorial image (by Amber Maalouf) collage for my newsletter, editorial shoot with Irina Shayk by Garth Aikens