Here’s another great example of how higher waisted trousers can give you nice proportions between your torso and legs, and how pleats can visually break up the expanse of fabric that sits on your hips and thighs. Ignore fashion writers who say that pleats should always be avoided, or that they’re only meant for heavier set men. There’s nothing wrong with pleats if the tailoring is done well, and you can find many good examples in Old Hollywood pictures from the 1930s through ’50s. Slim the legs down a touch, if that’s to your taste.
That polo shirt, incidentally, was made by Ascot Chang and is currently being sold through The Armoury (where the model above, Nick, works). You could wear it underneath a sport coat for a more casual look. The collar and cuffs will give you the look of a dress shirt, while the half-placket and pique cotton will prevent you from looking like you just came from the office.
Agreed, it’s important to not become too caught up in the dogma of current trends (i.e. no pleats etc) as you should dress to fit your frame. Higher waist pants will better complement most people and pleats (when tailored appropriately) are perfectly flattering.
Plus, to paraphrase Glenn O’Brien, pleats are an example of engineering, not fashion. They allow your pants to expand and contract with your body in comparison to the stretching flat front pants are forced to do. Anyone who’s squatted and blown out a pair of flat front trousers can attest to this design flaw.