Rolled up trousers work best on slimmer cuts, such as bootleg or slim fit but not skinny cuts, which would give a very feminine look. The trouser cut should follow the natural width of the legs, visually creating the illusion of one continuous line all along the length of the leg including the covered and exposed parts. On a wider cut, the rolled up end will result in too strong a contrast between the width of the trousers and that of the exposed leg thus, drawing the eye only towards the (shortened) length of the trousers. Low waisted cuts will also visually shorten the legs as they give the illusion that the legs start from the trousers’ waistline.
Pin rolls shouldn’t look too chunky, which is usually the result of too many folded layers or very thick fabric. Whilst turn-ups can give an extra dose of style to an outfit, being located too far down, they should never be the centre-piece. People should be focusing on your face, not your legs/feet. Therefore, trousers should never be too long as this will inevitably lead to more layers to fold.
How long you wear your trousers will also have a visual effect on your height. Rolled up trousersusually reach just above the ankle or slightly lower. However, men’s trouser lengths are getting shorter meaning your trousers can even be worn up to mid to lower shin, especially if complemented with a pair of boots in the same colour as the trousers and socks, allowing for the legs to look longer.
In fact, for short men to carry off pin rolls, the focus shouldn’t be limited to the trousers themselves but also to how the other pieces affect one’s silhouette. Monochrome is considered perfect for looking taller as it avoids that break-up of the silhouette into a top and bottom half. Therefore, it should make turn-ups safer.
However, monochrome can be a bit boring, not to say restrictive, especially given the limited range of colours that most men would feel comfortable wearing from head to toe. Hence, it’s OK to opt for varying yet, similar colours – a tonal look. You still don’t want too much of a strong contrast and always keep lighter tones on top as the other way round makes the top appear heavier.
I would also suggest to keep the belt minimal in a way that it blends in with the trousers’ colour, making it hardly noticeable. This prevents it from creating too strong a horizontal line that breaks the silhouette.
In addition to combining colours wisely, how your top layers fit, as well as their length also affects how short/tall you appear. Stick to shirts, tops, and/or jackets in your size which in combination with the trousers’ cut will keep your silhouette balanced (size-wise), as opposed to top-heavy. Just as you can make your legs appear longer by avoiding low-waist cuts, by keeping your tops to just below the waist, you keep more of your lower half exposed.
Rolled-up trousers and shoes combinations
Rolled-up trousers must be worn with the right shoes and my idea of the right shoes are those which keep your feet looking narrow but not necessarily longer. You want shoes that keep your feet looking proportional to the rest of your body whilst visually elongating the legs. Bulky shoes do the exact opposite. Moccasins, loafers, sandals with vertical straps, chukka and Chelsea boots, as well as Converse all look great with pin rolls even on short guys. Just as you’d avoid too much contrast between your trousers and tops, combine colours that give your lower half a flowing look. This can be achieved by opting for similar trouser and shoe colours, or which at least blend effortlessly with one another.
I know how fashion trends seem to be set with only tall men in mind and how disappointing it can be when the end-result is not what you hoped for. With these tips, I’m hoping you’ll be able to keep looking great and confident when wearing turn-ups. Just remember that the trick is to compensate by keeping the eye drawn vertically, thus creating the illusion of height.