Just an FYI to everyone: I’m cool with criticism and critiques, so don’t go feeling like you’ll hurt my feelings or anything. (Obviously, don’t be a dick though, as there’s enough of those on the Internet.)

Anyway, I see your point on the pants. Just to throw out some numbers, I typically got 7.5-8” (laid flat) on my leg openings. A couple of chinos I have from Brooks Brothers (Milano cut) came at 8” and I thought they looked fine and weren’t worth having reduced down toward my usual 7.5”. Most of my other grey trousers are 7.5”.

Could I go narrower? Sure. I have a few that are 7”, but I feel like that’s just not me most of the time. It looks like I’m trying to squeeze my body into this pair of pants designed to look like a lookbook model, which is definitely not my body type by any means.

I’m a bit tall and lanky, but my thighs are kinda big, my waist and gut fluctuate with my alcohol intake and that’s just what I’m working with. (Sidebar: I gained 2” on the waist last month. That’s what happens when you can’t cook for yourself and drink four nights a week for a month.) Plus, I do feel a bit restricted by “skinnier” cuts and I feel a bit looser cut still looks all right and just gives me more — ahem — movement.

Typically, for most pants I get, I have the tailor take in the seat (maybe the waist if it needs it) to avoid having “diaper butt”, and taper the legs the whole way through. I could maybe ask for a greater taper, but it’d look weird as my thighs are substantially greater than my mid-calf area. So, this would mean it’d be tighter in the thighs, or I’d have a wide upper leg and a super narrow lower leg. I opt to keep it even throughout — starting at the leg opening.

I feel like some guys go for a really extreme taper on their clothing, which is slimming and all, but I think you need to have the body structure for that to pull it off (ie: Street Etiquette).

Do I have my alterations completely correct or at a level of perfection? Nope, but I think it’s a process of finding what works for your frame and being realistic. You can’t just carbon copy your fit from models. I think part of this whole thing is knowing yourself, being comfortable with it and choosing the right clothes to suit your lifestyle.