About trousers and their length
First things first, some basic information: ideally trousers should help creating a slender silhouette, giving the impression of longer legs and a taller figure.
Therefore a golden rule for proper trousers length would state that on the front they should sit on the shoe breaking only once, close to the hem, and that on the back they should almost reach the heel with a straight line, without ever breaking at the hem.
In case you were wondering if this means that the hem should be slightly diagonal, the answer is yes, the back part of the pant leg being longer than the front.
Having this general rule clear in mind, we can now discuss how (and if) we can break it.
I personally very much dislike trousers that are too long and break multiple times on the shoe: not only they shorten the figure of the person wearing them but I feel they communicate a somehow scrubby and shabby image.
People wearing trousers this long tend to have also quite wide hems, which make the overall effect even worse.
The current aesthetic (in order not to call it “fashion”) in formal and casual menswear want us to adopt trousers that are slimmer, shorter and with smaller hems. Be also aware of the fact that there’s a strong trend for pleated trousers looming at the horizon ;)
I’m leaving streetwear out of the conversation because we’re talking about aesthetic and in my opinion streetwear is simply a big mess.
Back to the main point: being Italian, I have an obvious and foregone preference for the above mentioned shorter lengths, slimmer legs and smaller hem openings, allowing to show some fancy socks during winter and let my ankles breathe in warmer months/climates.
Wearing shorter lengths of trousers can be done to various degrees, which means that I usually adopt “short but not super-short” with formal trousers, where the pant leg is barely kissing the top of the shoe (thank you Thom Brown and your aesthetic) and “definitely short” with casual trousers such as five pockets and denim; in these cases I sometimes appreciate rolling up the hem myself, emphasizing the casual look.
On formal occasions I tend to respect the “golden rule” as much as possible, even though keeping on the short side of it ;)
What about you, how do you like the length of your trousers?
Quick note on the point mentioned at the beginning of this post: in general, straight lines and no breaks equal to a more uniform pattern and therefore a longer figure. This is the reason why, for example, a not so tall person will look better in a striped cloth suit than in a suit made of checked cloth, and the other way round for a very tall person.
If you’re reading this and you’re a tall guy, please do add some checks to the rotation of your vestiaire. You’re kind of lucky, take advantage of it.
NB: adopting trousers with a higher waist definitely helps in the initial effort as well ;)