In a recent post, my fellow blogger Chris Hogan referred to my distrust of the boat shoe. He suggested that one reason for this distrust was that “for some men the space between formal and casual is much tighter – like Simon or my father.”

I can understand why I might give that impression. I listed my preferred loafers as those with thinner, leather soles, a more elegant waist and – above all – without that fold of stitched leather around the toe. On a leather shoe that seems ugly and inappropriate to me. It is entirely a matter of taste, but that is where my taste lies.

However, from Chris’s description it sounds like the space between formal and casual is actually wider for me than it is for him. His preferred casual outfit is khakis, polo shirt and docksiders. I generally go for jeans, a t-shirt and an old brown leather jacket, probably with battered purple-and-brown Converse boots. So while my formal is more formal, my casual is more casual.

As stated, this is all a matter of taste. But Chris’s post prompted me to consider why I tend to these sartorial extremes. And I concluded that it is because is implicitly distrust the space in between formal and casual. It is tricky and many men get it horribly wrong.

Let’s start with some basic examples. There has been a horrifying trend in the UK in recent years of men wearing suit jackets casually, with t-shirts. It might work if the jacket was a rougher, more casual material – flannel, tweed, linen. But it was not. More often than not it was worsted, in blue, often with pinstripes. The t-shirt wasn’t a v-neck, let alone a polo shirt. It was high-necked and the jacket was worn open.

It is hard to imagine a combination that more effectively nullifies every flattering aspect of a jacket. There is no gorge, and so no plunging V in the chest. There is no waist (as it is worn open), and so no contrast with the shoulder width. There is generally no consideration of fit whatsoever.

Other examples: When men wear chinos casually they seem to think they will look good worn like jeans – very low in the waist, very long in the leg. They don’t. When they wear a shirt untucked they seem to think it matters little how long the tail is. It does. If it is a formal shirt, chances are the tail will be so long you will look like you are wearing a night shirt.

Now, the disclaimers. It is perfectly possible to do “the in between” very well. Tailored polo shirt perhaps, with a pale grey flannel jacket – shorter and less structured, but fitting well nonetheless. I’m sure that Chris does the in-between look very well indeed. And I am equally certain that the American readers of this blog wear the loafer/khakis/polo look very well, with no less attention to fit and effective colours than that given to their formal wear.

But I think they are the minority. Much of the in-between attire smacks of laziness because it is so often worn lazily. Chris mentioned his father – who has never owned a pair of jeans in his life and wears neat chinos with deeply polished loafers. Unfortunately, my experience is that for every ageing gentleman dressed this well, there are 10 that wear their old flannels with no idea of how they fit or how tatty they are. They may even – as I depressingly witnessed recently – wear trainers instead of leather shoes.

For better or worse, this puts me off the in-between look. And I’ll stick to my brown leather bomber for now.

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Interesting post. The original boat shoe the Sperry Topsider is extremely comfortable (v. many imatators that use a very inflexible plastic-like sole). It is worth recognizing that, at heart, it is a sporting shoe (yachting) and as such should be matched with items that are sympathetic to it (such as jeans, polo/t-shirt and Harrington following JFK’s lead). Worthy of mention is the style that falls between formal and casual – that of Street or Urban style. Drawing on neither traditional Country nor Tailoring influences it draws its influence from a fusion of modern sports (surfing, basketball, skateboarding) motor racing (biker jackets and boots) and, in recent times, a creeping military influence (field jackets, camo, ammo boots, courier bags etc.). I believe the growth in popularity of this style rests firstly on comfort and secondly on the ability to weave multiple influences and styles together to complete a unique personal look (biker jacket, bandana, punk style t, red jeans, Chuck Taylor Converse boots – for example). This mix and match draws from all the influences above but it is the personalisation of the ensemble that provides for the authenticity of the style.