Let’s talk about pants. Specifically the end of the pants. For two little openings that allow your feet to poke through, they are surprisingly complex and difficult to master. So I’m going to talk about a few rules and options when it comes to hemming your pants.
Rule #1 (and really the only concrete rule): hem your damn pants!
There’s few things sloppier than a guy walking around with a puddle of pants around his ankles. It makes you look like you stole someone else’s pants and completely ruins your silhouette. A pair of hemmed $30 chinos from gap will look better than an unhemmed pair of $250 flannels from Howard Yount. Almost as bad is just rolling/cuffing pants that are not meant to be cuffed. Rolling up dress pants or slightly more formal chinos/khakis with dress shoes just looks damn lazy. If it’s jeans or more casual pants like the 5-pocket variety, and it’s being worn with casual boots/derbies or sneakers, by all means roll ’em up. Otherwise, it’s 2017 and there are tailors in every shopping centre so please have your pants hemmed to the correct length.
To break or not to break
Pants can be hemmed to have a double break (two creases), single break (slight single crease), or no break (no cress at all). I personally don’t think there’s much need for double break for most guys, and the choice between single break or no break is a matter of taste. I first got into clothes via an interest in the ivy style of dress so my preference is for no break. Whatever you decide, also try to get the tailor to put a slight camber on the hem so the front is slightly shorter than the back. This is a bit harder if you decide to add a cuff to your pants.
To hell or high water
Of course the other option is to have highwater pants where there is a gap between the hem and your shoes, revealing a bit of sock. This is a bit of a fashion forward look and frowned upon by “trad”. I personally don’t mind the highwater look and I tend to employ it with pants that are a bit wider/straight fit and high-waisted. That way I avoid the homie-G connotations and it looks intentional. You can also do it with slightly tapered fit pants but I tend to avoid it with slim pants as I find it looks odd, especially since my legs are quite skinny.
To cuff or not to cuff
This is a matter of personal taste as well. Traditionally hemming the pants with a cuff is more formal. The idea of cuffing is that it adds some weight on the end of the pants so it pulls them down a bit and creates better drape. This is why I tend to always cuff dress pants, particularly if they are made out of linen or wool (which are materials that tend to drape better than cotton). For chinos/khakis I tend to cuff them if they are slightly dressier i.e. not 5-pocket, no visible stitching, mid-waisted. Plus I just like the look of cuffed pants. It’s an old fashioned thing that you don’t see very often anymore (outside of #mensstyle/Instagram of course). Now that I’m used to it, I find it odd to wear uncuffed pants with dress shoes. The fashion trend at the moment is to have a big 2-inch cuff but a 1.5 inch cuff could work better for shorter guys and may have more longevity when the big cuff trend wears off.
Leg opening width
Leg opening width is something most guys don’t think about. I often see guys with longish derbies and very skinny pants, which looks out of proportion to me. I read this very helpful post a while back. It talks about how the leg opening width should be matched to the shoe length and style of shoe so that it looks in proportion. Now this is a very “trad”/conservative proportion and not a hard and fast rule but it demonstrates how these factors can make your outfit look disproportionate.
Now that you know, please don’t let me see you with a puddle of pants again.