Untucked shirts: When and how

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Readers often ask whether I wear shirts untucked – usually at this time of year, when suddenly an untucked shirt seems delightfully cool.

The general answer is no but there are a few exceptions, enough to make it worth writing a full article rather than a one-word answer to a comment. In this article I’ve used some shots in our showroom to walk through variations on a single outfit, and demonstrate those exceptions.

Untucked shirts are easier, more relaxed and often more comfortable (comfort is, as we’ve discussed, as much psychological as physical) but in general – for most people most of the time – they are less flattering.

Consider the outfit below. Having the chambray shirt tucked into the chinos means there is a sharp horizontal line at my waist, emphasising what is almost the slimmest part of the body. It also means the legs appear longer – starting from that point rather than one lower down – and the shoulders appear broader in proportion to that shorter torso.

In this case having the shirt buttoned a little lower aids the affect, as it creates a longer V-shape on the chest. I’m slim and tall but not that broad, so anything that adds to the impression of breadth is helpful.

But flattery isn’t everything. There’s also style and propriety. Wearing a tailored jacket and trousers would be even more flattering on me – giving me shoulders I don’t have – but the formality would be completely different.

So here’s the first, most obvious exception to a tucked-in rule: when dressing very casually in the summer, I’ll won’t tuck my shirt in.

That’s illustrated in the shot below. I’m wearing shorts – and very casual shorts at that, vintage military ones – and to me a tucked-in shirt would be too formal. It’s not what I’m after when dressing like this. It’s hot, I’m off-duty, and there’s a good chance I’ll be doing something like chasing a five-year-old round a park.

Exception number two: an untucked shirt that’s really an overshirt.

I wear overshirts a lot at the weekend, and have written about a few of my favourite ones. These are usually thicker than a regular shirt, so I wouldn’t want to tuck them in even if it were possible.

But I also wear lighter shirts in this manner when the weather’s warmer – below is an example. The shirt and the T-shirt are the same, but the shirt is untucked and unbuttoned.

Note that the T-shirt is still tucked, retaining that horizontal line at the waist. This makes a big difference, I find, in stopping the overshirt look from becoming sloppy.

I like this outfit, and it’s the kind of thing a lot of more-casual-dressing readers could use I think (indeed, probably already do). The navy trousers with black belt and shoes make the whole thing smart/casual, but dark jeans and trainers would work too.

An interesting variation is doing up just one button on the shirt, somewhere around the waist. Carl at Rubato does this (he rarely wears a T-shirt on its own, there’s always a collar there somewhere).

The shirt has to be quite loose-fitted for this to work, otherwise it’ll kind of gape oddly when you sit down, but I like how it gives some shape to the shirt. The problem with untucked shirts generally is that they create this big, rectangular block that doesn’t flatter the physique; buttoning it at one point creates some shape, almost like the buttoning of a jacket. Plus you see some of that waistline underneath.

This is something I often emulate if I ever do wear a shirt untucked and buttoned-up (usually spurred by some combination of fatigue, heat and laziness).

In the shot below the shirt is untucked but it’s unbuttoned a little at the bottom, adding a little shape. You could unbutton the top more too, but that’s not for everyone; at the least have two buttons undone.

I don’t do this consciously, but I’m also aware that that block of shirt is broken up by having my hands in my pockets. I’ve done it in all these images without even thinking about it, and it certainly helps.

If you like this kind of untucked smart/casual look, one issue can be what to wear over the top. Tailored jackets are usually too smart, and bombers or blousons are too short.

Best are hip-length pieces like chore coats, or waxed and hunting jackets. In the image below I’m wearing a wool chore from Anderson & Sheppard over the fourth look above (the one-done-button). It’s a great deep, dark navy, and suits the smart/casual vibes of everything else. Not sloppy, but not dressed up either.

In case anyone didn’t see it last year, we did a series of articles on these kinds of jacket substitutes – chore coats, tebas, overshirts etc. You can find the first in that series here.

A last variation I thought was interesting to include was one showing the variations of layers I wear with overshirts.

During this past winter, I found that overshirts and jeans became my default at the weekend: the combination was simply and easy, but had enough variation to mean I enjoyed briefly picking out which ones to combine.

British winters are unpredictable though, and the weather went from mild to genuinely very cold. So I found I varied the layer underneath the overshirt depending on the weather – rather than trouble the rest of the formula.

The range went from nothing, to a vest, to a T-shirt, to a thermal. And there were two types of thermal – the Joe McCoy henley from The Real McCoys, which is a lovely cotton, and the wool crewneck from Stevenson Overall. The latter is incredibly warm, more so even than a cashmere sweater. That’s the Joe McCoy one below.

I’m sure untucked shirts are something PS readers will have views on – from considering them a crime against menswear to a wonderful, laidback style all their own, but hopefully this adds some nuance to that debate.

Clothes shown: