It’s one of those choices that seem straightforward. When one is required to look smartly-dressed, the shirt goes in and when a casual look suffices, the shirt remains untucked. Yet, if it was that simple, the outcome wouldn’t so often look so unflattering. Rather than choosing only on the basis of the smart/casual factor, consider also the actual length of the shirt, the visual effect of an un/tucked shirt on your silhouette, as well as how well your choice blends in with the rest of your outfit. The three need to be considered together, as one will affect the other.
Let’s start with the shirt’s length. This should not reach further below the level of one’s mid-buttocks (and not much higher either). A shirt, whose length extends beyond that level is too long for the person’s height. If worn untucked, it’s too likely to result in a sloppy look, making wearing it tucked in, the better option. This will hide the fact that it’s too long.
On the other hand, when a shirt is so long as to result in the ‘excess length’ bunching up under your trousers, it’ll feel somewhat uncomfortable, especially if the trousers are tight-fitting. Depending on the thickness of the trousers’ fabric, the result could also be rather unsightly. If it’s too long, just don’t buy it.
However, even if a shirt is in the right length, wearing it tucked in or not, could also be matter of wanting one’s legs to appear longer or shorter. This, in relation to the upper body. Leaving a shirt untucked will visually extend the torso, especially when the shirt’s colour isn’t similar to the trousers’, consequently, minimising the legs’ length (visually). This is usually an option more suitable for taller men, whose legs tend to be very long in comparison to the upper body. By making these look shorter, one creates a better balance between the upper and lower parts of the body, effectively creating a visually more proportionate silhouette.
In contrast, shorter men, whose legs tend to be short in comparison to the upper body, will look better wearing their shirts tucked in. By leaving more of the trousers exposed, one creates the illusion of longer legs. An untucked shirt risks visually accentuating the imbalance between the upper and lower parts of the body.
Finally and equally important, is considering the overall style of one’s outfit and how each individual piece (and how they are worn), contribute to the desired style. Wearing a shirt tucked in will not automatically result in a more professional or dressy look. It could still maintain the casual style in an outfit.
However, whether the way you wear your shirt ties in with the rest of the outfit, also depends on how casual or versatile the other pieces are. For example, on a pale pair of jeans and sports shoes, a shirt is better worn untucked otherwise, the smarter look of the tucked in shirt will clash too much with the laid-back effect of the jeans and sports shoes. Similarly, if wearing a sport coat, a tucked in shirt will compliment the overall style better than if worn untucked.
There was a time, not so long ago, when it was considered trendy to wear one’s shirt partly tucked in. David Beckham often sported the look himself. As is usually the case with trends, they have a short lifespan. Nowadays, a partly tucked in shirt will just look like a job half-done – it’s either one or the other.