This has got to be one of the more ignored or misunderstood topics out there. At least if the appearance of the man on the street is anything to judge by. The right cut for your clothes is crucial to middle ground dressing.
Today’s garments are trimmer — which I find a good thing for most men. I almost didn’t add this rule as I hope that everything that you have in your wardrobe has been rigorously tailored and altered to best effect. I mean everything. Sportcoats, shirts, trousers, jeans, khakis and shorts … take ’em all to the tailor, regardless of their styles.
Can you get away with pleated trousers? Yes, provided they fit you perfectly, are laundered and creased (starch helps) and don’t droop below your belly making the pleats expand. (That is why they work best with suspenders/braces.) Your shirt should be equally well cut and tailored to fit. Floppy and baggy looks careless these days. Full-cut oxford cloth button-downs? OK. But, as much as I hate to say it, starch them.
Another good example would be to compare an older overcoat of yours to a newer one. The newer will be cut slimmer. Chances are it doesn’t have to go over a suit coat. It is made to be thrown directly over a sweater or shirt.But you may still have to have the sleeves shortened for it to look good. Long sleeves on any suit, sport coat or topcoat again look careless.
Find the right cut for you and wear it correctly.