IN CONVERSATION WITH CASSIDY MONTALVO

interview by JANA LETONJA

Cassidy Montalvo has built a digital presence that feels less like a feed and more like a conversation with a trusted big sister. A lifestyle and fashion creator with over 2.7 million followers on TikTok and 1.1 million on Instagram, she’s known for her warm, nostalgic approach to modern dressing, pairing classic silhouettes and romantic details with an ease that feels genuinely attainable. Through her platform Just Classically Cassidy, she shares everything from viral hair hacks to quiet moments at home, blending humor, honesty, and heartfelt advice. Alongside her work as a creator and founder of the jewelry brand I’Mperfect Collective, Cassidy continues to expand her influence, most recently attending New York Fashion Week, where her timeless point of view stood out amid the season’s ever-shifting trends.

Your content carries a strong “big sister” energy. Was that something you set out to create, or did it evolve naturally?

It evolved very naturally. I am a big sister and come from a big family, so it is just part of who I am. When I started sharing online, that same instinct showed up in my content. The “big sister” energy is really just me wanting women to feel encouraged and more confident when they leave the house. If I can drop tips along the way, that make their journey a little easier or give them a boost like a good sister should, then I have done my job well.

Just Classically Cassidy celebrates vintage-inspired style in a very modern way. What draws you to classic silhouettes and neutral palettes?

Trends are exciting, but there is something powerful about pieces that transcend seasons. Neutrals and timeless tailoring give you a strong foundation, and from there you can layer personality. Things like color, texture, and accessories add individuality to timeless pieces without losing that sense of polish. I will always respect designers who can take classic silhouettes and neutral palettes and make them eye-catching and unique while still maintaining top-tier elegance.

How do you balance nostalgia with making fashion feel relevant and wearable right now?

I have always said nostalgia is another word for inspiration. I love pulling references from past decades and blending them with modern trends, but I always ask myself, “How would this woman dress today?” Updating a nostalgic look through texture, pattern, proportion, and styling is the easy part, because many designs from past eras are inherently timeless. The real artistry comes from finding your personal style and giving those classics a unique twist while still preserving their elegance.

You share both polished moments and imperfect ones. How do you decide what parts of your life to keep private?

I share intentionally, not constantly. My audience sees a lot of my life, but the moments I keep private are the ones that need to stay sacred, like family time, certain personal challenges, and anything that in my gut feels like it should remain protected for the sake of my family and my mental health. I think boundaries actually make authenticity stronger.

Attending New York Fashion Week is a big milestone for any creator. What did that experience mean to you personally?

NYFW feels like a full-circle moment. I grew up reading fashion magazines cover to cover, wallpapering my room with Vogue clippings, and dreaming about the rooms where new designs would be shown. Walking into those spaces as part of the industry, not just watching from afar, has been incredibly emotional and motivating. I always think about the little girl I was, who never believed she would be good enough to make it into those rooms. To be at NYFW in any capacity means the world to me because it allows me to live out the dreams I carried for so long, and that is such a blessing.

How did being at NYFW influence the way you think about fashion, trends, or your own style voice?

It reminded me that personal style matters more than ever. Trends move quickly, but the people who truly stand out are the ones who understand who they are and dress with intention. Being there encouraged me to lean even further into my own aesthetic rather than chasing what’s trending.
This season especially, we are seeing a resurgence of color, rich textures, and multiple decades being reimagined at once, which is a powerful reminder that fashion is cyclical. Individuality is what makes it feel modern and fresh.

In an industry that moves quickly, how do you stay rooted in timelessness?

Timelessness comes from knowing your core aesthetic and having the confidence to stand in it. I love experimenting, but I always return to the pieces that feel unmistakably me, adding small, unique touches that keep the look personal. When you understand your foundation, trends become accents rather than direction, which is what keeps your style grounded and lasting.

Your audience has grown completely organically. What do you think people connect with most in your content?

I think people connect with my honesty. I love fashion, but I also talk about the journey and building confidence. I have shown myself growing through different seasons of life, sharing my mistakes, and allowing myself to reinvent when I feel called to evolve, especially since I have grown my audience from my twenties into my early thirties, which is such a transformative time for most of us.

Style becomes much more meaningful when women feel seen, not just styled. I try to show my audience that they do not have to have everything perfectly figured out to show up beautifully in their lives. Confidence is something you build over time, and fashion can be a powerful tool in that process.

Jewelry is clearly personal to you. What inspired you to launch the I’Mperfect Collective?

Jewelry has always felt emotional to me. I wanted to create pieces that were not just accessories, but small reminders of moments and meaningful milestones. Launching I’Mperfect Collective came from that belief that the things we wear every day should tell a story.

The brand celebrates individuality and meaningful imperfections. How does that philosophy reflect your own life?

Life rarely unfolds perfectly, and I have learned that some of the most beautiful moments come from what did not go according to plan. That philosophy shaped the brand, celebrating individuality and the idea that imperfections are often what make something unforgettable.

Even now, I’Mperfect is in a season of change as we reshape what it will look like. We are evolving imperfectly, just as we all do, but we continue to move forward.

As a creator, entrepreneur, and style voice, how do you balance creativity with the business side of what you do?

I try to treat creativity and business as partners, not opposites. Creativity builds the vision, and business protects the longevity of that vision. When both are respected, you can create freely while still building something sustainable.

Looking ahead, what does growth look like for you—creatively and personally?

Growth for me means expanding my impact while staying aligned with who I have always been. Creatively, I want to continue evolving in fashion, storytelling, design, and honesty. Personally, it is about building a life and a brand that encourage women to feel confident stepping into the next version of themselves.

TEAM CREDITS:

talent CASSIDY MONTALVO
photography ABIGAIL MILLER
editor TIMI LETONJA
interview JANA LETONJA