Meet Bentley Caldwell

Tell us a little about yourself. How did you go from working in music to fashion?

I’m originally from a small town in Kentucky called Paducah. I was transferred to Nashville about 13 years ago with retail. I always tell people, “Retail brought me here, but music kept me here.” Shortly after moving to Nashville, I began pursuing a music career as a singer-songwriter. In 2018, while on tour in the UK, I came to the conclusion that I was finished with playing music. I finished out the tour, came home, won some awards and shut it down! Shortly after I hung up my music career, a friend hit me up. He had to record some videos for a new coaching business he was launching and had ZERO idea what to wear. I gave some clues and tips on what to wear and it blew his mind! He ended up becoming my very first client ever and Bentley Caldwell Styling was born!

Could you share with us the experience of being featured in the NFocus Magazine? How did it come about, and what was your initial reaction?

NFocus Magazine is a really prestigious magazine here in Nashville. I first had the privilege of being featured in NFocus as a model. When I was launching my styling business, NFocus reached out to a local designer to style their Men’s Style Issue. With it not being his area of expertise, he ended up referring them to me. I’ve styled their last three Men’s Style Issues (Gracing the cover of one!) and it’s been a beautiful relationship ever since. Seeing my face on the cover of a magazine was CRAZY! They didn’t tell me! I literally said, “Holy SH*T!” when I saw it! Haha It was such an incredible experience. I started writing a men’s style column with them as well! Truly grateful to them.

What are some mistakes people tend to make when styling themselves? What is your creative process on how to create a good look?

Following trends. Trends are FOREVER changing. If you try to keep up, you’ll end with a closet full of clothes you never really wanted and can’t wear anymore. When I’m creating a good look, for me, I always start with pants and shoes. Then, I work my way up. Shoes and pants are the anchor to any good outfit! Once you have those established, you can pretty rock any top you want!

What is the most important thing to remember when styling someone?

Each person is unique. They have a unique personality. A unique view of themselves. A unique set of life goals. My job is to unearth that. My job is to put them in a wardrobe that helps them look and feel their absolute best, not to put them in a costume. That way when they look at themselves, they see an elevated version of themselves. Not a caricature.

What do you think is it about clothes that have been loved for a long time and remain unchanged that attracts people's interest?

For me, I think it’s the memories these items hold. For example, I bought the green military jacket in the photo when I was in college at a clearance sale at The GAP. It was $9.99. I thought it was the coolest jacket! I wore it anytime I wanted to feel “cool.” When I moved to South Korea after college, I took it with me and it felt a bit like home.

While I was over there, I bought that red pair of John Varvatos Chuck Taylors. At the time, that was an expensive sneaker for a formally broke college kid. $90 for some Chucks?? I ended up trading the original laces for the black ones. I immediately felt like a badass. I wore those shoes until the soles literally wore out. I keep them because they remind me of an important time in my life… The first time I ever leveled up.

What are some of your favorite brands and designers?

Obviously, I love Kato. I really dig the simplicity of Buck Mason. There’s a menswear designer here in Nashville named Eric Adler, that I really dig. His suiting is top-notch! I really love footwear as well! Two of my favorite bootmakers are White’s Boots and Danner out of the Pacific Northwest. And I LOVE a little sneaker brand out of L.A. called Brandblack. Some of the best sneakers on the market!

What are some misconceptions about styling?

A big misconception is that styling is just about the clothes and that’s 100% not true! I tell people all the time, “I’m not in the fashion business, I’m in the people business.” Styling is not “one size fits all” nor is it “copy and paste.” Each person is unique and has their own set of needs, wants and ideas of how they want to look. My job as a stylist is to distill that information to help them feel and look their best! As a stylist, you have to be able to have great people skills and expert problem solving skills as well. And I pride myself on having both!

How did you hear about KATO and what do you like about our brand?

Oh man! I first heard of Kato from a local store in Nashville called Franklin Road Apparel! I love denim. More importantly, I love selvedge denim, but the break-in process of raw selvedge is too rough! Haha When I found Kato’s selvedge with stretch… It was a game-changer! I love the fact that you get the selvedge denim look and feel, but you can actually move! I put my first pair of Pen Slims on and never looked back!

Do you have any items from KATO and what do you like about them? Can you give us 3 tips on how you would style KATO?

I have MULTIPLE items from Kato! I love the craftsmanship. Once you put on a Kato piece, you can tell it’s well made and it will last you for a very long time. For me, like I said earlier, a good look starts with shoes and pants. What better place to start than with a good pair of Pen Indigo Black Raw(My personal favorite wash) jean? From there, depending on the formality of where you’re going, toss on some sneakers and a tee shirt or some nice boots, button down, a jacket and you’re out the door! It’s really that simple! I like to toss on a bandana or a hat to round the look and add a little bit of flair!