Waist and Seat
Dress pants and wool trousers should fit perfectly around your waist with no need for a belt to hold them up. They should hit around the high hipbone area, or even slightly higher. You do not wear wool pants at the same waist as jeans – which are usually designed to sit lower. Saggy pants is a big no no.
The seat, or butt area, should lightly hug your butt and not be saggy or super tight. If it feels like you’re going to split your pants, they’re way too tight. If you’ve got a bunch of extra fabric around the butt, they’re much too loose. A tailor can fix this, it won’t be easy or cheap, but if everything else on the pants fits properly, definitely get it done.
RealMenRealStyle has the perfect illustration of how the seat of your pants should fit:
You want to be able to pinch around 1/2″ to 1 inch of fabric on either side of your thigh. If it’s less than that, your pants are too tight. If it’s more, have your tailor slim the thighs.
Knee to Ankle
If you’re a thin to regular build, the pants should have a slight taper so that it gets narrower towards the ankle, like the image below. This will look great on this body type/size.
If you’re a thicker/wider guy, you want the pants to be cut straight down from the knee to the ankle – like how your jeans should fit. This will balance your proportions nicely. If you went with a taper here, it’d make you look very top-heavy.
Hem & Cuff
Always default to having your pants hemmed to leave a quarter (also called slight) break. It looks more polished and sharper than a full break and no break at the hem is a time & place kind of thing, and not generally for everyday wear. A slight break works for everyone.
A trick I do with all my clients is to have the tailor hem the pants so that it’s slightly longer at the back of the hem. That way, when you’re walking, you’ll show less sock and when you’re standing still, it’ll lay nicer on the top and back of your shoe.
There are very few times, I’d argue almost never, when you’d cuff your dress pants or wool trousers. I’ve never cuffed pants for a single client because it’s not necessary, no matter their body type.
If you’re not familiar with the different type of pant breaks, PrimerMag has some great images to help you understand:
See my Wool Pants and Trousers Essential article for my favorite wool pants for men.
See the bottom of my Wool Pants and Trousers article for details.