For Bentley Caldwell, styling isn’t just about clothes—it’s about connection. Before launching his men’s styling business, Caldwell had already worn many hats: musician, model, actor and lifelong retail pro. But his official foray into wardrobe consulting began unexpectedly when a friend launching a coaching business needed help looking polished on camera.
“I took him through my process—Closet Detox, curated Shopping Day, follow-up session—and when he tried on the first outfit, I heard him exclaim from the fitting room,” Caldwell recalls with a laugh. “He came out and said, ‘Dude, I’ve never looked this good in my life.’ I knew I was onto something.”
Caldwell’s relationship with fashion began in church, where dressing well was a given, even without designer labels. Later, a stint living in South Korea opened his eyes to global style. “I could read GQ on the train to Seoul and then buy the exact pieces I saw in the magazine. That just didn’t happen in Paducah, Kentucky!”
His light-bulb moment came during his music career, when a stylist friend helped him align his stage look with his sound. “Visually, I looked like I sounded vocally. It changed everything.” Now, Caldwell does the same for his clients—many of whom arrive feeling “overwhelmed by style” or sent by a well-meaning spouse.
The first step? Connection. “I want to know who he is. I’m not putting him in a costume. The wardrobe has to highlight what’s already great about him,” he says. And if the chemistry isn’t there? “I don’t work with jerks,” he grins.
From there, Caldwell brings his mantra—Elevated Simplicity—to life. He teaches clients to invest in quality, prioritize fit and keep things timeless yet fresh. His process is straightforward: a Closet Detox to clear out what’s no longer serving them, a pre-planned Shopping Day to fill the gaps and a follow-up to integrate the new pieces into daily life.
It’s as much about mindset as it is about materials. “Working with me is a judgment-free zone,” Caldwell says. “I like to think of myself as a ‘fashion therapist.’”
For Caldwell, the goal is simple: “When you look good, you feel good—and when you feel good, you carry that confidence into every part of your life.”
Fall Styling Tips from Bentley Caldwell
- Don't be afraid to layer. One of my favorite looks is jeans, hoodie, boots, and a topcoat or jacket.
- Embrace the suede! Whether it be a suede jacket, a pair of suede loafers, or boots, don't be afraid of the suede.
- Don't be afraid to try different textures and patterns. The beauty of fall and winter clothing is that you can play with tweeds, herringbones and different fabrics and patterns. So go for it! Have fun!
And if/when in doubt, reach out to a stylist to help you. We'd love doing this stuff!
bentleycaldwellstyling.com
@bentleycaldwell