At some point in your life as a grownup, you will purchase pants that come with an unfinished hem. They will probably sit in your closet unworn, for a couple of weeks at least, as you forget to bring them to the alterations tailor day after day.
When you finally get them to the tailor, he or she will interrogate you about what you want done to the ends of your pants. Your tailor’s questions are typical of menswear, in that there is a range of answers consistent historical norms, but absolutely any answer is bound to enrage a menswear enthusiast somewhere. This inevitability is one of the great pleasures of dressing. This article attempts to prepare you for the choices that lie ahead (or below?), and suggest whose hackles you might enjoy raising the most.
Question 1: Would you like cuffs?
Some people will tell you that pleats are a necessary and sufficient condition for cuffs. These people don’t know what they’re talking about.
I cuff everything. The extra weight at the ankle helps the trouser leg hang straight. It’s also slightly more casual. Since cuffs supposedly began from the aristocratic habit of rolling up trouser bottoms when walking through mud in the country, some people still insist that they are inappropriate for business suits. These people are excellent targets for trolling, and I suggest you cuff your business suit trousers if for no other reason than to drive them batty. But it’s up to you. You can cuff any pants you want, as long as they are not for black tie, white tie, or morning dress. Also remember that you can always take a cuff out, but adding a cuff back in is usually impossible.
Question 2: How much break would you like?
Now we get to the issues that may cause actual riots. If your pants are too long, you’ll be attacked by a swarm of bloggers chanting “casual elegance.” Too short, and you will face solemnly wagged fingers from people who lump cropped pants together with misuse of “whom” and the designated hitter rule as signs of our impending cultural collapse.
Ideally, you want a slight or “shivering” break, following Luciano Barbera’s famous edict to “show your shoes, but not your socks.” This makes the leg line as long as possible - any longer and it gets broken by the cloth folding over itself. In practice, this is basically impossible to achieve at all times, because 1) walking or anything else that bends your leg effectively raises the hem of your trousers 2) unless you’re wearing suspenders, throughout the day your trousers will tend to slide down to your hips, lowering the hem of your trousers.
You have to find your own peace with these competing demons. You can mitigate the first issue by getting a slanted hem - longer in the back than the front. This will keep the back hem closer to the shoe. You can also hem narrow pants a little shorter than wider pants, because they’ll bounce around your ankle less. Which brings me to:
Question 3: Do you want the pants tapered? Widened?
My general advice is not to do this. You’ll need somebody competent to enlarge or constrict the leg opening equally on both sides of the leg. If this is done incorrectly, the leg will twist in one direction or another.
But if you’ve got someone you trust, you could try widening if you are a larger waist size. Tapered pants below a larger waist, especially above larger feet, is a particularly unattractive silhouette. Or perhaps now I’ve just revealed my own casus belli.