Today we’d like to introduce you to Lana Ashby Rowder.
Alright, so thank you so much for sharing your story and insight with our readers. To kick things off, can you tell us a bit about how you got started?
Sure! I never set out thinking I’d start a fashion tech company—but looking back, it all makes sense.
I was a nurse for years and loved taking care of people, but after having kids and stepping away from the hospital, I found myself staring into my closet feeling totally overwhelmed. My body had changed, my lifestyle had changed, and suddenly getting dressed felt… hard. And I knew I wasn’t alone—my friends, especially fellow moms, would constantly text me asking what to wear to events, date nights, family photos, interviews—you name it.
The idea for lookingGLASS honestly nagged at me for years before I finally went for it. My husband was the one who said, “You keep talking about this… maybe it’s time to actually do something with it.” That little push was what I needed. I went back to school to get certified as a personal stylist, and that’s when everything started to click.
I realized there was this huge gap: most people don’t want to hire an expensive personal stylist, but they also don’t want to keep buying random clothes from influencer links that don’t work for their body or life. So I created lookingGLASS—an easy, friendly platform that helps people get dressed using what they already own, with real outfit help from real stylists. We combine AI with actual human connection, and we make confidence and personal style feel way more accessible.
Today, we’ve been featured in Forbes, WWD, and we’re even doing a demo at CES 2025. But at the end of the day, I still get the most joy when someone says, “I like they way I look again and I feel great.”
Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
It has definitely not been a smooth road. It’s been the bumpiest of all bumps—and honestly, it still is.
I’ve dealt with imposter syndrome more times than I can count. I’ve cried for days, taken days off because I didn’t even know what I should be working on. I’ve had trademark issues. I’ve been scammed by app developers. I’ve redone our website three times. We rebranded. Changed our name. And the hardest part? I had to lay off my first employee because we didn’t have the funding to keep going.
Fundraising has been its own beast—hearing “no” over and over and over again, trying not to let it shake my belief in what we’re building. There have been so many moments where I questioned myself, my path, and whether this was ever going to work.
But even in all of that—somehow, I kept going. I believe in this. I believe in the people we’re helping. And every bump, every mistake, every hard day has taught me something I didn’t know I needed to learn.
As you know, we’re big fans of lookingGLASS. For our readers who might not be as familiar what can you tell them about the brand?
I’m the founder of lookingGLASS, a personal styling platform that helps people get dressed using clothes they already own. We combine real stylists with AI to make it quick and easy to get outfit advice—whether you’re heading to a wedding, an interview, or just trying to figure out what to wear on a random Tuesday.
We specialize in simplifying style. Our members don’t have to scroll Pinterest for hours or waste money on another haul that doesn’t fit their life. They can just text a stylist and get help—right then and there. No pressure to buy anything new unless they want to.
I’m most proud of how personal and real we’ve kept it. Our stylists are kind, down-to-earth, and totally nonjudgmental. We meet people where they are—whether their body has changed, their lifestyle shifted, or they just feel stuck in a rut.
What sets us apart is that we’re not trying to sell people more stuff. We help them make better use of what they already have—and feel good doing it. It’s not about trends. It’s about confidence. And we’re making that accessible for people who’ve never seen themselves in the fashion space before.
We’d be interested to hear your thoughts on luck and what role, if any, you feel it’s played for you?
Oh, luck has definitely played a role—but not always the kind you hope for.
There’s been plenty of bad luck: getting scammed by app developers, trademark headaches, spending time and money on things that totally flopped. There were moments where I honestly wondered if the universe was trying to tell me to quit.
But the good luck? That’s shown up in the people. The team I have now—every single one of them came into my life in a way that felt random but also… kind of meant to be. I met some at networking events, others through mutual friends, and a couple I’ve known for years but reconnected with at just the right moment. The timing was uncanny.
Those relationships, that support—that’s the kind of luck I’ll take any day. Because without them, I wouldn’t have made it this far. They believed in me and in this vision when things were messy and uncertain, and that kind of luck is something I’ll never take for granted.
Pricing:
- Memberships start at $95/month
- One Time Styling starts at $100
Contact Info:
- Website: https://lookingglasslifestyle.com/collections/all-services
- Instagram: https://www.instagram.com/lookingglasslifestyle/
Image Credits
Alissa Cordoba Photography
