It’s always interesting when I receive a DM that begins with “I know there are bigger things happening in the world, so I feel silly writing you….” Or better yet, “don’t think I’m a total asshole for asking this question.” It’s consistent, statistically speaking, that many people who message me are highly concerned with appearing either frivolous or pretentious, or some combination thereof, when discussing personal style. And at times, such expression is conveyed through a whisper and head bowed in a bit of shame. Because I consider learning how to identify and show your personal style as anything but frivolous, I’ve been exploring what drives this behaviour. You’ll be relieved to know I’ve found the culprits.

Just Google “shows about fashion.” The results are deeply polarizing. On one end of the spectrum, you are “either in or you are out” . At the other end, you are just flat out; you get to peek in, but make sure you know your place. And, by ‘place’ I either refer to the size of one's wallet or some official permission that is conferred to you to be considered a “creative.” A bit of financial or artistic voyeurism. Listen, I find the aspirational films on McQueen or Raf at Dior to be creatively stimulating. I will for sure just flatline to a Project Runway binge. But whilst entertaining, this content does not speak to personal style. They are places I go to learn about someone and their craft, but rarely do I glean anything I can apply to my life.

You can understand why these two extreme views taint any discussion around style. And, this sucks. It really sucks. Because indisputably, visuals speak loudly. They tell a story about you. And I think it makes sense that if they’re going to tell a story, it should be one that you’ve written. I like to be in control, to the extent that anyone ever can be, of how I’m being perceived. I have three ways of doing that: through the consistency of my words, my actions and my visuals. They’re interconnected that way. For me. And from what shows up in my DM’s. I know it’s true for you as well.

So, first things first. Just because the media-led discussions have devolved into a shit show of either ridiculousness or divisiveness, it does not mean that a solid, rational middle ground doesn’t exist. It does and I have proof. For the purpose of this conversation, let this reside as a fact in your head. When we’re done discussing, you can decide if you still feel silly or overly affected. My bet is you’ll feel neither and that, in fact, you’ll feel smarter or at least a bit more satisfied to know the origin of your angst with regards to caring about fashion.

First, I think it’s helpful to admit to yourself why you care about personal style. For me it’s because (and not in any order):

• I don’t ever want to feel like a poser.
• Creativity fuels me.
• I’m really curious as to why things are the way they are and I extend this curiosity to how combinations of clothing and accessories make me feel.
• I hate wasting money and wish I could get back all that I spent on items that I never wore or made me feel so mentally uncomfortable with myself.
• I think buying smarter ultimately results in buying less which is beneficial to my wallet and the environment.

You know the saying “that person is comfortable in their own skin.” This statement refers to confidence. Not the type that is derived from “wearing a bold color” or “putting on a statement-making shoulder pad” but rather from visually conveying you are at ease with who you are. Part of that ease comes from understanding the environment you are in - being part of it without losing yourself. Appropriate. And I don’t mean in a country club dress code attire sort of way. I mean that you are embracing the spirit, environment or traditions of the area you are in while still retaining your sense of self. To me, that is style nirvana. In my life, I often find myself in many environments that do not reflect “the way I grew up.” I don’t use the words outside of my comfort zone, I just mean factually speaking, it’s different than what I experienced before making my way in the world. Whether religious, cultural, or even financial, I love being able to maneuver and be part of different places whilst still feeling like myself. I grew up in an environment where I didn’t take my first vacation that required an airplane until college, but I can now say I’ve been on one of the finest yachts in the world. I grew up going to church, but have now bar-mitzvahed my boys, hold deep friendships with people of every religion, or none at all, and find myself navigating regularly between a range of cultural customs. I’ve sat courtside watching tennis tournaments in towns with one traffic light as well as the clay courts of country clubs where the dress code is posted next to a sign asking that your kids stay seated and quiet at this week's family BBQ.

All this to say that I think a lot about how I have felt in all these different environments. No matter where I am, I’ve come to realize that confidence comes from feeling like myself and feeling appropriate in the environment that I inhabit. Never feeling more than nor less than. The balance. It’s important to me and it’s what I think most about when creating the line with Traci, our head of design.

Here’s what I mean. The cargo skirt here has the balance of refinement, the unpretentiousness of the ease of cotton, and the modernity of an interesting color combination that strikes it all just right. Little things like the trouser fly front gives the feeling of something quite tailored-but-not. Understated whilst still making a statement - even if that statement is just between me and myself.

If I mix the skirt with a terry cloth sweatshirt, I’m at ease by sitting fireside in Montana and fully comfortable sipping wine at a gravel side table at La Chiusa in Tuscany. Worn poolside, this is chill enough that I’m feeling content in Ibiza but could navigate any Cape Cod seafood shack while still feeling right at home. Paired with a tube top I’m chic in Miami, but if you were to drop me onto the porch at La Residencia in Mallorca, it’s all good and right. Comfort and ease come from feeling like yourself in places that are quite opposite in vibe and terrain.

I think a lot about the dichotomy of the places we travel to and the desire to still feel like yourself no matter where you land. People always ask if I design specifically for customers in each region. The answer is no. I design for an individual that is chill, modern and appreciates craftsmanship - in whatever form that takes. And that mindset resides in many different regions and spaces in life.

Here’s another example of the deceptively simple-but-not denim dress. The front snaps and large pockets give it loads of relaxation, but the seaming details and the defined bra cup give it structure and modernity. It’s that balance that makes you feel at ease shopping for cheese in Bagnols, France, heading to the office in Shoreditch, sitting courtside wheather it's watching Djokovic playing at Wimbledon or simply your kid learning to follow through with the ball.

Perspective is something I try to imbue into our designs. I don’t claim, by any stretch, to be able to view things from every angle through my life experiences. However, I do try and think about what makes me feel at ease in most situations. Undoubtedly, as far as “the visuals” go, it comes down to having key pieces that can morph and become better with each new surrounding and experience without fundamentally changing its core. Which is probably how I think about myself as well... come to think of it.