Overcoming the Imposter Syndrome: How Taelor Can help
It’s a common story, whispered in conference room corners and hidden behind carefully crafted LinkedIn posts: a sharp-dressed man in a leadership role, maybe even a CEO, who secretly feels like he has no idea what he’s doing.
Despite the résumé, the promotion, and the glowing performance reviews, there’s a persistent inner voice muttering: “One day they’ll find out I don’t belong here.”
This is imposter syndrome. And men experience it more often than they admit.
Expert stylists assisted by AI to pick items that match your preferences and occasions.
Rent up to 10 items per month to get ready for the week and achieve your goals.
Easy return to get your next shipment or buy to keep your favorite items.
The Silent Struggle of the Successful Man
Imposter syndrome doesn’t discriminate by gender—but while women are more encouraged to talk about it openly, many men keep their doubts to themselves. The cultural narrative often tells men they must be confident, put-together, and always in control. Vulnerability doesn’t always have a place in the boardroom.
But behind the polished smiles and smart suits, many professional men wrestle with the feeling that they’ve somehow “faked it” into their success. In fact, in a recent interview on the podcast Coffee with Cher, Taelor’s Founder and CEO, Anya Cheng, revealed that she herself struggled with exactly this kind of self-doubt. She was not into fashion, but just wanted the right clothes to give her a professional image without spending too much time thinking about them. She found help with subscription services for women like Rent the Runway and Nuuly, although that too required spending time scrolling through options on their websites.
She soon discovered that a large number of high-performing men felt the same as her. Even though they’ve built amazing companies or climbed the corporate ladder, they still feel out of place in the role.
Clothes Make Confidence
Here’s the thing: how you dress affects how you feel. As they say, "When You Look the Part, You Start to Feel the Part."
Studies in psychology back this up. “Enclothed cognition” is a term researchers use to describe how our clothing choices can influence our confidence, performance, and even our thinking. When we wear clothes that match our aspirations—or project authority, creativity, or sophistication—we begin to embody those traits more easily.
But for many men, figuring out how to dress well is a burden. Fashion trends are confusing, in-store shopping is overwhelming, and the idea of spending hours figuring out what works for your body and lifestyle? Not appealing.
Clothes become this source of stress. And, like Anya, many busy men are looking for style without stress. This need laid the seed for Taelor.
Enter: Your AI-Powered Style Wingman
Taelor is not just a menswear rental service. It’s a personal brand accelerator.
By combining advanced AI with expert personal stylists, Taelor takes the guesswork out of dressing well. Every item is handpicked to suit the customer’s personality, goals, body type, and lifestyle. The result? Curated outfits that help men look like they belong in the room—whether that room is a pitch meeting, investor conference, date night, or casual Friday.
“You don’t have to know fashion,” Cheng explained. “You just tell us about your life, and we take care of the rest. And when you look good—like, really good—you carry yourself differently. That confidence builds over time.”
Expert stylists assisted by AI to pick items that match your preferences and occasions.
Rent up to 10 items per month to get ready for the week and achieve your goals.
Easy return to get your next shipment or buy to keep your favorite items.
No More Wardrobe Anxiety
One of the most surprising insights Taelor’s team uncovered is how much mental space men dedicate to something as seemingly trivial as “What should I wear today?”
When you’re already dealing with high-stakes decisions at work, imposter syndrome lurking in the background, and the pressure to always “show up,” the last thing you want is to feel unsure about your appearance.
Taelor eliminates that friction. With each delivery, members get premium clothes that they can wear with confidence—no shopping, no laundry, no long-term commitment. Just great style, always on tap.
And because the service learns from your feedback over time, your outfits get better and better. Like a wardrobe that evolves with your career.
Real Stories, Real Impact
One Taelor user, a startup founder in San Francisco, put it this way: “I never realized how much my confidence at work was tied to how I dressed. I used to wear the same three shirts to every pitch. Now I actually get compliments—and more importantly, I feel like I belong.”
Another executive said: “Taelor helped me show up as the version of myself I always wanted to be—but never had time to figure out how to dress like. Now my team sees me differently. And so do I.”
Looking Ahead
Imposter syndrome may never fully go away—but how we respond to it matters.
By removing one source of uncertainty—your wardrobe—Taelor helps men reclaim their mental bandwidth, show up with more confidence, and, perhaps most importantly, start seeing themselves the way others already do: as leaders.
In a world where first impressions matter and self-doubt can creep in even at the top, dressing well isn’t superficial. It’s strategic. And with Taelor, it’s also effortless.
Because when you look the part, you start to feel the part. And eventually, you become it.
Want some help finding clothes that will make you the best possible version this season? Let Taelor help. Taelor is a menswear rental subscription service dedicated to helping men look their best when it matters most. Our styling service, powered by a human stylist and assisted by artificial intelligence, finds the clothes that help you win – at work, on a date, at a party, or wherever you spend your time.
