I have written about the six button fronts, the vintage look and how lowering the second button on a custom shirt helps to create that perfect, classic casual look. Lowering the second button, if you are making a custom shirt, or buying a six button front is the ideal. Without a doubt these are the superior choices which give you the perfect casual balance. But what if you don't have a six button front shirt? What if you aren't able to order a custom shirt? What do you do with all of your other shirts? Do you unbutton two buttons? Do you unbutton one button?
The problem with unbuttoning only one button in a casual environment is that it still looks too buttoned up. The problem with unbuttoning two buttons is that it may (and often does) read as if you are trying too hard to be "cool". Some people have incredibly strong opinions about this. Some people think that if you aren't wearing a tie, you should have two buttons undone. One button is not an option, they say. I think that if someone hates the way one button looks then they should unbutton two, if people hate the way two look, they should unbutton one. It is simple. It is your own personal style. This is a very niche discussion. This isn't some make or break. There really isn't anything "wrong" with either way. If someone says there is some objective thing wrong (in totality) about either way, they are probably just being hyperbolic out of boredom. Whenever people make the smallest subjective details into make or break, it's always a sign the bigger picture is missing.
My perspective, from my personal approach to our style is as follows. I think that one or two looks just fine in lots of different scenarios. I think that unbuttoning two buttons looks natural in the most relaxed settings. Some of these settings would be at the end of the day, the weekend, an outfit with no sport coat or blazer, working outside, on a hot summer day relaxing with no jacket. I think tw0 unbuttoned looks great in these scenarios. I think that outside of those situations, generally one looks better. I personally don't think two unbuttoned looks so great with a blazer or sport coat. I think on many guys it looks like one is trying too hard to be "cool". I think there is a southern Europe / Italian influence in the commitment to unbuttoning two buttons. I think that is fine. I love Italy and I love the way lots of Italian guys dress. But, they have a certain attitude, certain spirit, certain feeling of life. They are in Italy as well, in the summer. Italy is very hot in the summer. The unbuttoning of two buttons even when wearing a sport coat, blazer or suit compliments them very well. Does it compliment everyone? Does it feel (or look) natural on every guy that does it? I am not so sure.
On a work day, wearing a sport coat or blazer (I never wear suits) with no tie, unbuttoning only one button suits me most naturally. It is not optimal on a commonly found modern shirt. The optimal is a six button front or a custom shirt with a lowered second button. But, even on a common seven button front, it is more natural and feels more right to me, than unbuttoning two. It doesn't feel right in that scenario. In other very casual scenarios like mentioned early, it absolutely does feel right. But in this situation - of a blazer or sport coat and no tie - only one button seems more right.
An example of two buttons unbuttoned in the most relaxed setting
If you look at the old photos, the classic photos, men almost never have two buttons unbuttoned. Of course, they are wearing six button fronts, that second button is lower, yet still they almost never have two unbuttoned. Personally, I get more of my influence from older photos rather than the modern Italian influenced suiting. I don't really feel a need to work to "feel cool". I am married, I have kids. I am comfortable as myself. Yet, for younger guys, in the dating game, considering how our style is already perceived as so formal , I do understand in their case perhaps a need (or want) to make some little changes here and there to have things read a little more youthful. That is a bit of a separate topic, I will write more on that in the future.
Yet, even in the case of the younger guy, I am not sure that unbuttoning two buttons is what he wants to convey. Maybe it is, maybe it isn't. Guys have different approaches and what works for one guy doesn't work for another. All that said, not feeling the need to unbutton two buttons for this (what seems to be) attempt to appear as more hip because one is confident as himself may share something in common with the wearing of a pink OCBD. There is a certain sort of confidence in the pink OCBD. Some guys don't wear it, despite it being a classic. Just as there is a certain kind of sureness and confidence that comes with wearing the pink OCBD, there may be a certain kind of sureness and confidence of not needing to unbutton two. There really is a thread through our whole style which is about quiet (and sometimes not quiet as seen in the case of the GTH pant) confidence.
An idea that is core to my style approach is one of longevity. I want the photos of myself to look good today and tomorrow. I want my approach to hold up. I want to establish a personal style which is almost immune to trends. Of course we get pushed around a little bit. We wander here, we wander there. We go through different phases in terms of what feels right to us. That is normal. Yet, I think about the constant. Personally, for my approach, at my age, even when wearing a modern seven button front shirt, reserving the unbuttoning of two buttons for only the most casual moments feels right and natural. And the point of our personal style is to feel natural, feel right, feel organic presentation. For others what may be natural is two buttons, for me it is one. When developing our personal style we should always keep our eye on what is true to us and our natural lives. We should consider different ideas from outside of ourselves, we should experiment with different tweaks here and there, we should consult other inspiration (I don't dress in a continental European way, but I do get inspiration [especially in thinking] from some men in this area even it it doesn't seem like it), while always coming back and keeping our eye on what feels natural.
As for the other details of this classic summer outfit, everything is standard fare - nantucket red chinos, white OCBD and a navy blazer. The one notable piece is the cool green/blue madras belt. Generally I suggest erring on the side of caution by keeping a bold madras belt like this as the only particularly notable / non-neutral item in an outfit. Yet it can, like you see here, be pulled off alongside another non-neutral piece if you are careful and know what you are doing. In the case of this outfit, the non-neutral piece is the nantucket red chino. The madras belt fits nicely right in between the red of the chinos and navy of the blazer with the white of the OCBD in its own corner. It feels like everything is spread out evenly and in proportion. If you would believe it, I picked up this madras belt for just $9.00 from a J. Press warehouse sale. I couldn't resist.