After I retired the tuxedo — a decision I wrote about in the last post — I overcorrected. Badly.
The logic seemed sound at the time. If the problem was dressing too formally, the solution was dressing more casually. So I showed up to a corporate event in Vienna wearing dark jeans, a black crew-neck sweater, and clean white sneakers. The look was what fashion magazines would call “elevated casual.” I thought I looked modern and approachable.
The audience was in suits. Not fancy suits — standard corporate attire for an evening event at a financial services company. But suits nonetheless. And there I was, the person who was supposed to command the room, looking like I had wandered in from a coffee shop.
I had traded one problem for the inverse of the same problem. Before, I was overdressed relative to my audience. Now I was underdressed. Both errors had the same root cause: I was not calibrating my appearance to the specific context I was walking into.
This is when I started to understand that the goal is not to dress up or dress down. The goal is to be the best-dressed person in the room — which is fundamentally different from being the most overdressed person in the room.
The Calibration Principle
Dan Harlan’s costume advice in his Tarbell Lesson 83 lecture contains a deceptively simple principle that I keep coming back to: wear something that is a little bit better, a little bit different, a little bit more stylish, a little bit more you than everybody else.
Every word in that sentence matters. “A little bit” is the operative phrase. Not dramatically. Not conspicuously. A little bit. The difference should be noticeable but not jarring. It should register as “that person looks sharp” rather than “that person is wearing a costume.”
This is harder than it sounds, because the line between “best dressed” and “most overdressed” is genuinely thin. On one side of the line, you project confidence, taste, and authority. On the other side, you project self-consciousness, effort, and separation. The audience reads both instantly, and they read them through the same social lens they use in every other area of life.
Think about it from the audience’s perspective. When you see someone at a party who is dressed slightly better than everyone else — a nicer jacket, better shoes, a small detail that stands out — you register them as someone with good taste. Someone who cares about how they present themselves. Someone who might be interesting to talk to.
When you see someone who is dramatically overdressed — a three-piece suit at a barbecue, a cocktail dress at a casual dinner — you register something different. That person is performing. That person is trying. That person has misjudged the situation. It is not a judgment of their taste. It is a judgment of their awareness.
For a performer, awareness is everything. If the audience sees you and thinks “this person does not understand the room they are in,” you have lost credibility before you open your mouth.
My Calibration System
After the Vienna underdressing incident and a few more experiments in both directions, I developed a system. It is not complicated, but it requires discipline, and it starts days before the performance.
Step one: research the event. I ask the organizer what people will actually be wearing, not what the dress code says. As I mentioned in the last post, the stated dress code and the actual dress code are often very different things. “Business casual” means different things at a tech startup than it does at a law firm. I want to know the reality, not the aspiration.
Step two: build my outfit one level above the expected reality. If the audience will be in jeans and button-downs, I wear dark trousers and a tailored blazer. If they will be in business casual, I wear a suit without a tie — or a suit with a tie if the occasion warrants it. If they will be in full formal attire, I match them in quality and add one distinctive element — an unusual lapel pin, a pocket square in an unexpected color, a jacket with more texture or character than a standard suit.
Step three — and this is the step most performers skip — I look at the complete outfit in my hotel room mirror and ask myself one question: “Does this look like it belongs in the same world as the audience, or does it look like it belongs in a different world?” If the answer is a different world, I adjust downward. If it looks like it belongs but could be sharper, I adjust upward. The sweet spot is when it looks like it belongs in the audience’s world but stands out within it.
The Distinctive Element
The “a little bit more you” part of Harlan’s principle deserves its own discussion, because this is where personality enters the equation.
Being the best-dressed person in the room is not just about quality or formality level. It is about individuality. Harlan describes his own performance look — the blue velvet jacket — and what strikes me about that choice is that it is specific. It is his. It tells you something about who he is. It is not generic “nice clothes.” It is a deliberate statement.
I have been developing my own version of this over the past couple of years. For me, it tends to center on one element that is slightly unexpected. A jacket in an unusual fabric. A shirt in a color that most men at corporate events would not choose. A watch that starts a conversation. Something that gives the audience a detail to notice, a reason to think “that person has interesting taste,” without overwhelming the overall impression of professionalism.
The key is that the distinctive element has to feel intentional, not accidental. An unusual shirt color works if it is clearly a deliberate choice, coordinated with the rest of the outfit. It does not work if it looks like you grabbed whatever was clean. Intention communicates taste. Randomness communicates carelessness.
I learned this lesson the specific way, by wearing a patterned shirt to an event in Linz that clashed slightly with my blazer. Nobody said anything, but I caught it in the photos afterward. The shirt on its own was fine. The blazer on its own was fine. Together, they looked like two good choices that had not been introduced to each other. The impression was not “distinctive” — it was “disorganized.”
Since then, I lay out every element of my performance outfit together, on the bed in whatever hotel room I am in that night, and I look at them as a complete composition. Not as individual pieces. As a whole. Does this outfit tell a single, coherent story? Does every element support the same message?
What “Best Dressed” Actually Means
I want to be precise about this, because the phrase “best dressed” can be misleading. It does not mean “most expensive.” It does not mean “most fashionable.” It does not mean “most attention-getting.”
Best dressed means most appropriate, most polished, and most intentional — all simultaneously. It means your clothes fit properly, your grooming is impeccable, your shoes are clean, your colors coordinate, and the overall effect is one of quiet authority.
Fitzkee was adamant about this. His costuming and grooming section in Showmanship for Magicians reads almost like a military inspection checklist: fresh linens, freshly cleaned and pressed clothing, well-groomed hair, clean hands, manicured fingernails, spotless shoes. Every time. Without exception.
What strikes me about Fitzkee’s list is how much of it is about maintenance rather than fashion. It is not about wearing the trendiest clothes. It is about wearing your clothes in perfect condition. A simple outfit that is perfectly maintained will always beat an expensive outfit that is wrinkled, scuffed, or poorly fitted.
This aligns with something I have noticed in my consulting career. The best-dressed executives I have worked with are rarely the flashiest. They are the ones whose suits fit like they were made for them, whose shoes are always polished, whose shirts are always pressed. The quality is in the details, not in the labels.
The Comfort Factor
There is a practical dimension to this that rarely gets discussed: comfort affects performance. If you are wearing something that does not fit properly, that pinches or pulls or rides up, you will carry that discomfort in your body. And the audience will read it.
I performed once in a jacket that was slightly too tight through the shoulders. It looked fine standing still. But every time I raised my arms — which happens constantly when you are performing — the fabric pulled and I instinctively hunched to compensate. I did not realize I was doing it until I watched the footage later. My shoulders were slightly raised throughout the performance, my movements were slightly constrained, and the overall impression was of someone who was not entirely comfortable.
The audience cannot diagnose the cause. They cannot see that the jacket is too tight. What they can see is that the performer is not fully at ease, and that impression undermines everything else. If your clothes are fighting you, you cannot project the relaxed authority that makes an audience feel they are in good hands.
I now have a movement test for every performance outfit. In my hotel room, I put on the complete ensemble and then run through the physical demands of my set. I reach overhead. I bend forward. I gesture broadly. I turn sharply. If anything restricts, pulls, rides up, or shifts out of place, that garment does not make the cut.
This sounds excessive. It is not. The freedom to move naturally on stage, without any part of my brain monitoring whether my jacket is bunching or my shirt is untucking, is worth the few minutes of testing.
The Adam Conversation
When Adam Wilber and I were building Vulpine Creations, we had a conversation about brand presentation that extended naturally to personal appearance. Adam’s insight was characteristically direct: the first thing anyone sees is how you look, and they decide within seconds whether you are someone worth listening to. Not based on your credentials. Not based on your reputation. Based on the immediate visual impression.
This is not shallow. This is how human cognition works. We are visual creatures, and first impressions are formed before the conscious mind has time to evaluate the evidence. If your visual impression says “professional, sharp, someone who takes this seriously,” the audience gives you the benefit of the doubt. If it says anything else — too casual, too formal, too costumey, too random — you start with a deficit.
The good news is that this is entirely within your control. Unlike talent, which takes years to develop, or reputation, which takes time to build, your visual presentation can be optimized immediately. The right outfit, properly fitted, well-maintained, and calibrated to the context — this is something you can get right tonight, for tomorrow’s performance.
The Ongoing Refinement
My approach to dressing for performance continues to evolve. Each event teaches me something new about the relationship between appearance and audience perception. A tech conference in Innsbruck taught me that a blazer without a tie reads as more approachable than one with a tie in a room full of engineers. A gala in Vienna taught me that matching the formality of the room is more important than standing out when the room is already elegant.
The principle remains constant even as the application shifts: be the best-dressed person in the room, not the most overdressed. Look like you belong in this world, but look like the sharpest version of someone who belongs. Dress like the host of the event, not like a visitor from a more formal dimension.
Every audience, every venue, every occasion has its own sartorial center of gravity. Your job is to find that center and position yourself slightly above it. Just slightly. Just enough that the audience registers you as someone with taste and authority, without registering you as someone who is performing the act of being well-dressed.
The performance begins the moment they see you. Make sure the first message is the right one.