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A Bellwether Friend: Bentley Caldwell

by Priya Pappu |

Bentley wears the Sashay pocket.

Bentley wears the Adieu pocket.

Bentley wears the Proud pocket.

Bentley wears the Stand kerchief.

Photo Credits: Jessica Leigh, Guillaume Lechat

We are very excited to debut a new series today: A Bellwether Friend.

Clifton+Leopold was created as a vehicle for Living Your Best Life. We like to think of ourselves as curators of an aspirational lifestyle - a large part of this lifestyle being fashion, of course, but it reaches far beyond that: to travel, interior design, art, food + drink, the sky's the limit. 

This series aims to delve into the dapper lifestyle as a whole by chatting with our bellwether friends in their respective fields - we can’t wait to share what we have planned! 

We couldn't think of a better, more talented, creative to kick things off with than Mr. Bentley Caldwell. Recently, our Founder + Chief Proprietor, Christopher, sat down with Bentley for breakfast to have a conversation about his work + ethos. We'll allow him to introduce himself below + their conversation follows:


Bentley Caldwell is Nashville's premier Men's Personal Stylist. He has a passion for working with everyday men, helping them take the guesswork out of shopping and upleveling their style.

With more than 15 years of retail and fashion industry experience, Bentley uses his intuition, instinct, and understanding of style to create an invaluable service that helps men take their image and confidence to the next level.

Bentley’s styling work has been featured in various Nashville publications and he has recently been added to NFocus Magazine’s contributor team with his own monthly style column.

To find out more about Bentley, visit his website at:
You can also follow Bentley on Instagram: @bentleycaldwell


Interview edited for clarity & brevity.

C: Talk to me about how you think about fashion - what is the story you're telling?

B: My personal style varies day to day. Yesterday I was full on dress pants, button down and tie, and then today I’m in jeans, a thermal and letterman jacket.

C: And looking great!

B: Haha thanks, so for me I think of my personal style as being a maverick...I don’t know maybe that is too big of a word...

C: Why? I love that idea of finding your inner maverick! 

B: It’s one of those things where anytime I see something I think “how can that be better." So with styling - there are a lot of great stylists in Nashville, doing great things, especially commercial - like videos, and commercial shoots. So for me, it was like I like that, but I don’t want to do it like they are doing it. So even when I am styling a photoshoot, I don’t style it like someone else would style it. I don’t approach it like anyone else.

C: Yeah, that makes sense. I mean, you are putting YOUR stamp on it. How do you think about styling yourself? Here’s what’s interesting- we’ve hung out a few times and you always look impeccable and it is always completely different.

B: For me first and foremost I have to love the piece. You know when I see it in the store or online I have to be like 'Oh I need that.' Like this letterman jacket I have on right now, I got it in a store in Seattle & I literally saw it & said oh my god YES.

What I usually do is get statement pieces and just know that when I get it home I will have something to put it with. Or sometimes I will buy it and go I’ll figure it out down the line...

C: Totally - and I think if not that way it is a missed opportunity! I know people who will say 'I’m going shopping for this' and I never have that, I might walk in and find nothing or I might wake up the next day like 'God I have to return this' you know but I never stop myself. The idea that an event will show up that needs me in this is just my thinking.

B:always joke - I rarely ever regret buying something, I have definitely regretted not buying something. So I’m like I’m going to get this, and know that I will eventually wear it.

SO in putting outfits together, I fill my closet with 1) things that I know I am going to wear and then 2) things that fit within the landscape of my wardrobe. Like sometimes you have to go and just buy a normal pair of jeans, not everything has to be a statement piece.

My thing is have a solid foundation of foundation pieces and then you can add the statement. I guess that would be my personal style and approach.

C: So a good foundation gives you freedom.

B: Yeah a wardrobe is like a house - build you a nice house and then you can add the nice furniture and appointments and paintings and whatever whatever.

C: I love that. A good friend of mine, we were talking one time and he was like - everything doesn’t have to be a 10. You know, a 6/4 is a 10 and 1/9 is a 10. So that freedom to have a couple things shine is a cool take.

One of the things we talk about a lot with the brand is all about writing your story. I think about it like this - I have pieces where I can tell you the things I’ve done in that particular item of clothing because it is etched on me.

B: Well your clothes hold memories - they really do-


B: With my clients I’ll do this thing where we do a closet detox and get rid of stuff that they just literally have physically outgrown or their life has outgrown. Like they’ll have the suit from their first job 10 years ago and I’m like why do you still have this suit? And they’ll say - that’s the suit I went to my first job interview in or blah blah blah, it’s like we all know and remember THAT moment.

C: I love how you put it - clothes hold memories.

B: Like you said, clothes tell the story of who you are. It's the thing that like you said, every time you see me it is a different outfit but-

C: You’re the same person - like I can find a through line in it-

B: Exactly!

C: I think that is what is interesting about trying to get people to go outside of their comfort zone. I mean one of the things we like to do with C+L is push people. Like I know you never thought you could wear an ascot/kerchief but MAN YOU CAN! If you know your through line. So when you are working with clients and trying to get them to push their boundaries, what is that conversation like?

B: It's one of those things that is a little different. You know I get guys who are regimented in what they’ve already worn and they are bored. And they’re like - I don’t know how to wear anything different!  So I say - look, I pulled some things you probably wouldn’t pick for yourself, and just try them on. You don’t have to buy them, you just have to try them on. No pressure.

C: Oh yeah, could you talk about the mirror moment for them when they see themselves for the first time...

B: Yeah it is totally a mirror moment. I had a client who I picked a short coat but it had a little nap to it, so it had little pops of color - like the top of a pop tart, haha. But it was a great jacket!

C: Umm, where was this jacket? Because I want to buy it.

B: He said "I’m not going to lie, I didn’t think it was great on the hanger, but then when I put it on- I would have never picked this up for myself!" That's the thing - I’m not trying to put you in a costume, I am trying to elevate who you already are.

C: Let’s talk 2023 - what are some of the fashion trends or things on your radar that you are looking forward to? That you see changing?

B: I am really loving this retro vibe in menswear-

C: LOVE IT! Our whole spring line is anchored in the idea of flashing back to the late 70s/80s.

B: YES! I am really digging that! I love the new approach to suits. So, well-fitting but with the wider lapels and-

C: Wider ties!

B: Wider ties and even a wider leg opening. I’ve always been into the more slim pant, but then I saw a friend wearing a white jean that was more relaxed and I  immediately went and bought a pair and I can’t stop!

C: And you nailed it. The wider lapel and collar.

B: Now, not baggy, I mean you still need to put in the effort. When the shoulder is like down here and you just look messy - not here for that. You still need to be fitted and tailored.

C: I think that is interesting - the bigger loser feel and more comfortable is so hot right now, but you can look comfortable and not be sloppy. I wonder sometimes if this freedom and feel isn’t encouraged from the time lost with COVID.

B: Oh yeah I think you’re right. In a round about way we were all cooped up and missed out, and the kids came out like 'fuck it...I’m going to wear whatever the fuck I want' - I’m doing it.

C: That’s my thing- you don’t have to go all the way, just a little bit-

B: NO you have to go YOUR all the way.

C: I love that. COVID was terrible, but I am always looking for a silver lining in everything - it’s how I live. And I wonder if the lining isn’t the freedom to just go hard and be you. Don’t hesitate. Like you said you never regretted buying something, I’ve never regretted wearing something - I’ve regretted not wearing it. 

One of the things we talk about as a brand is that clothes don’t have gender. How do you approach this with clients?

B: That is so funny you bring that up because I only style men, or let me say it like this: I only style “men’s” clothing and people who wear mens clothing.

I actually had a woman reach out to me and ask me style her, and I only knew her as very fem. But she was like - no I want to do a photoshoot for my 50th bday and I want to wear only suits. So we are doing a custom suit for her, and you know we’ll need some C+L haha!

We had this conversation about gender roles in fashion and how much I love women in suits - just make sure it fits! I love a woman in a bow tie. I just love seeing people being themselves - so if you feel comfortable as a man wearing a dress or a skirt, I’m like man GO FOR IT. 

People forget we have both energies in us, and it is more than ok to speak to both. To try to be 100% all the way either direction is unhealthy. 

So for me, I love pops of colors and florals and those used to be considered fem.

C: I love how I feel in pink!

B: Absolutely! And I’m speaking from a hetero male point of view - anytime I put on a floral or something that could be deemed feminine or used to be seen that way, I almost feel even more empowered - you know, maverick. 

C: I think the point is giving others permission. I keep going back to the guy in the blue nap jacket - you gave him permission to try on something, and then love something that he would have missed out on.

B: Yeah we’re all asking for permission - can I do this? AM I good enough?

I love it when people are dressing outside of gender or comfort zone because you just gave permission to others to do the same thing, they just needed someone to lend them confidence. 

C: YES - that takes me back to the thing you said before that will be my takeaway from our conversation - the idea that they don’t have to go to your comfort zone or level but they have to go to their new boundary just out of their comfort zone. They don’t have to be anyone else, but it is fun being an elevated version of yourself.


It's rare to see Bentley dressed without a pocket square, and who could blame him! In honor of Bentley, we're offering 20% off of our pocket collection. Just use code BENTLEY at checkout to start making a statement. 

And if you need a little inspo - Bentley was kind enough to style a few looks incorporating a C+L pocket. This styling session is on the house - you'll have to book him (through his website) for your next one! Thanks Bentley! 

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