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Photography: Daniel Baraka

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Mastering Men's Style

Styling the Men of Nashville with Bentley Caldwell: Trends, Traditions and Tailored Transformations

Article by Kit Garrott

Photography by Provided by Bentley Caldwell

Originally published in Belle Meade Lifestyle

Belle Meade Lifestyle got a few styling tips and insights from Nashville's Bentley Caldwell. As a men's personal stylist, writer and style influencer, Bentley knows his way around a suit. From groom styling to everyday outfits, Bentley has his finger on the pulse of the trends and the classics. 

Can you walk us through the typical process of starting with a new styling client? How do you understand their style preferences and wardrobe needs?

My process always starts with a phone call. I really like to get to know my clients. I'm not putting them in a costume, so I like to know their likes and dislikes—their wants and needs. 

Once we've agreed to work together, the first step in the styling process is the Closet Detox. I go to the client's house, and we sort through their closet and get rid of old clothes. I like to start with the client's closet because it gives me a better understanding of who they are, what they like, how their clothes fit and what they need for their wardrobe. 

From there, we enjoy an entirely pre-planned and customized personal shopping day at various stores in Nashville and Franklin. I'm all about efficiency, so I don't want a client to hire me, and then we wander aimlessly around the mall! 

Once we finish with the Closet Detox and Shopping Day, I put everything in a Digital Style Book as their fashion reference guide! Like your own personal style handbook!

How do you stay updated with the latest trends and fashion influences? How do you incorporate these into your styling recommendations for clients? 

I read a lot of fashion magazines and blogs, and I follow a lot of really stylish guys on Instagram. To be honest, I try not to follow too many fashion trends. What's in one season will be completely out next season. If you try to follow trends, you'll end up with a closet full of mess that you'll never wear again. 

I like to adhere to classic American fashion with European sensibilities. It's timeless. 

When creating a new look for a client, how do you balance their personal style with current trends and your creative vision?

My goal is to make my clients look and feel their best. Men often come to me because they're in a fashion rut, and my older clients have been wearing the same things for years and have no idea what to do or change. In both cases, I take their current style and update it with some current pieces without losing their sense of self in the process. The whole point is for them to look and feel like the best versions of themselves!

What is a common challenge you encounter when styling men? 

The two most common challenges that men face when being styled are body image issues and imposter syndrome. Like women, men also suffer from body image concerns. Either they're too short or too tall. Their arms are too long or short, shoulders too broad, torsos too long, etc. I've heard it all! 

The most common concern is that they think they have a "Dad Bod." Listen, as you get older, your weight shifts - it happens! I always tell my clients, "No one is paying attention to it more than you are." The imposter syndrome comes into play with the elevated wardrobe. Most guys go from being completely unnoticed to being the best-dressed guy in any room they walk into. I always tell my clients, "You'll grow into it."

What are some of your favorite style tips?

  1. Always have an anchor for your outfit: light with dark, dark with light, patterns with solids. It's more settling on the eyes.
  2. Shoes complete the outfit.
  3. Consider adding a third piece to every outfit, such as a bandana/pocket square, watch or hat. This takes an outfit from "decent" to "great." But don't overdo it! Keep it simple.
  4. Remember to cuff your short-sleeved button-down shirts and your chinos and jeans.
  5. Condition your leather shoes at least once a month. Take care of your leather, and it will take care of you. Leather is a skin, treat it as such.

Who are your favorite fashion follows right now?

Here are some of my favorite fashion follows:

Sergio Ines (@Whatmyboyfriendwore) runs an informative style account.

Brian Chan (@Bchanism) runs a cool and instructional account.

Jim Moore (@jimmooregq), Former Creative Director at GQ, is an absolute Legend!

You can follow Bentley on Instagram @bentleycaldwell for all your men's style content, including special event "Get Ready With Me" videos, styling tips and his clothing and accessory recommendations. Bentley has honed his process down to a few packages that you can choose from on his website: The Junior Package, The Standard Package and The Executive Package. 

Bentley prioritizes finding the right fit in clothing and styling assistance. His eye for what works, and more importantly, what works on you, is at the heart of what he does so well. 

bentleycaldwellstyling.com

"I like to get to know my clients. I'm not putting them in a costume."