What Sits Under Your Taste (and Decides What You Buy)

Men often tell me they like certain things. That they like how certain men dress. Another guy will tell me the exact opposite.

How associations shape your personal style

We call it taste, but what's underneath it are your associations. A Western denim shirt means cowboys to one man, while to another it's just the shirt he saw Kanye West wear in a double denim look, and the aesthetic hooked him. It is the same shirt but with a completely different meaning.

Those associations are data. A piece works (or doesn't) because of the memories and signals it plugs into. Every piece you're drawn to carries a few, and since it's "just" clothes, most guys have never looked at it that way. And that, gents, is exactly why the closet is full while the rotation is... dying for some new blood.

If you want to find your personal style as a man, this is the layer to study first: the associations behind what you already reach for, save, and buy.

Let me paint you a picture.

A client of mine bought the same pair of drawstring trousers ten times. Yes... ten times. From Isaia, no cheap brand either. It was the exact same style; the only difference was in the color. This is how most men approach building a wardrobe: they just replicate what works. That means the result never reaches the level they originally had in mind. And that makes sense. In what world would you eat different-colored capsicum every day in an attempt to develop your palate for the rest of your life, just because it tasted good once? Just saying.

Unlike paprikas, Isaia trousers retail anywhere in the $1,000+ range, so this palate experiment isn't one you'd want to keep repeating for every category that follows. The underlying thing: my client was trying to buy back the feeling the first two brought to his wardrobe, and that feeling doesn't come folded in a box.

That pattern is worth sitting with, because almost every man I work with runs some variation of it. The closet is overfull, the rotation is thin, and everything in between is a big question mark. Fabric and fit alone aren't enough. The explanation: we're rarely drawn to a piece of clothing itself. We are drawn to what it stands for.

The James Bond problem

I see the clearest version of this in my style discovery process. I ask clients what car they drive and which one they wish they drove, what style has meant to them, and whose style they admire. A remarkable number of them say Daniel Craig in James Bond. Or David Beckham. Only to then send me examples of them in the most basic outfits known to man.

Because when we look at what Bond wears, it's mostly a suit or a pair of pants and a polo. Inside the suits, he's a well-tailored man. Outside them, his clothes aren't extremely special, and there's no styling secret to reverse-engineer.

What these men are drawn to is the setting. Context. The message the whole appearance sends. The fact that Bond's never there to play nice or look for approval. That's the association, and it produces a very different shopping list than the one they walk into a store with. You can't buy Bond or Beckham off a rack, but you can absolutely waste years trying.

The same thing happens on a smaller scale every time you save a photo of an outfit. You think you're saving the jacket, but often you're saving the color combinations of the outfit, the setting or mood of the photo, the posture or aura (I hate that word) of the man inside it, or the life the setting implies.

If you buy the jacket without separating those layers, the jacket arrives, the feeling doesn't, and you file it under "didn't work" without ever knowing why.

A little analysis

Said client recently purchased a seersucker jacket with matching pants. Loved it. It was a beautiful wool seersucker set by the Italian label Altea.

Then he got tempted by a sale at one of his favorite stores. Staff knows him well. He ordered a similar set, also seersucker, in his colors, but from another brand: NN07. The pants were okay; the fit of the jacket was off. We talked about possible reasons why.

Here's his data:

• Drawn to the style of Stanley Tucci: composed, with a bit of quirk
• Wore suits for most of his career. A kind of uniform. He knew fit, fabric, silhouette, and there was room within it for personality. A pattern, detail, an accessory. A David Yurman piece here, a nice silk tie there, a good watch, shoes
• Fit: tailored, sharp, good-looking, Italian-leaning
• A build men would kill for at his age
• 80% of his casual wardrobe: Italian brands
• Fit and fabric were always the priority; now comfort is non-negotiable too

The pattern behind the Altea set follows that data closely: the tailored Italian cut, the luxury materials, the attention it was made with, and the interchangeable details like shoes, underlayers and accessories to play with inside that perimeter.

The NN07 set, on the other hand, was a polyester variant from a Scandinavian brand, aimed at a completely different audience. Same concept, different look, and a completely different data set.

The Altea set worked because it matched everything his suit years had built: the Italian cut, the real fabric, the uniform-like sharpness that still left room for a quirky detail.

The NN07 set only matched him on the surface. Because seersucker, his colors, a set, combined with half the original price all add up to what looks like a valid reason. In reality, it was a boxier, more relaxed Scandinavian silhouette. Designed for a young guy who wants to look like he isn't trying but magically looks good in whatever he grabs.

My client has spent thirty years looking like he tries. So take that fact, and the polyester, the slightly different cut, and a brand ethos that doesn't align: of course the jacket felt off. His data had said no already. Four times.

And that's the point of all this. Taste is tempting, but understanding the association that draws you in comes first. And that starts in your own wardrobe, without having to spend $10K just yet.

Run the question first

So before you buy anything, ask yourself what it is about the piece that actually speaks to you, because whether you like it was never the question. You already know you like it; that's why you're holding it. Is it the cut you were trained on for decades? The world the brand belongs to? Is it just because some attractive woman once mentioned it was "hot"? Or a stylish guy you know wears it who seems to pull everything off? The setting you saw it in? Or is it the discount (which is really just the feeling of winning, and wears off right after tapping "pay")?

If the answer turns out to be something real, then this is a question that follows naturally: what do I already own that carries this? Let the first buying place be your closet, because most men with a full wardrobe and a thin rotation already own the association they keep paying for again in slightly different colors.

If there's nothing there, that's a good place to start from. Write down this data, because it might just save you some cash, time, and thinking you like something while you don't.

Nice clothes were never just about the look. They go as far as the meaning you've attached to them, which means the men who dress best aren't the ones who own the most, but the ones who know exactly what they're buying.