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I go cuff on about 75% of my suits. IMO always put a cuff on a pleated pant, and alway go no cuff on flat front. Since I am taller i don't mind the cuff, but on short guys the cuff makers them look shorter. In general the street used to be pro-cuffs, now it doesn't matter one bit. Most high-fashion (italian, etc) suits these days will have flat-front pants.
I'd disagree, no cuff definitely looks good with some pants but I think the cuff helps with having the pant sit well on the shoes; especially when you're on your feet a bit or are in a rush, you don't want the awkward too-far-forward look (you guys know what I'm talking about). More importantly, make sure you get good quality, 100% wool dress pants. And yes, always wool, don't mess with anything else.
With the younger guys, no cuff, flat-front is now becoming the trend. Pleats are designed to be more comfortable, and the cuff is designed to put more weight on the bottom of the pant leg, thus maintaining the pant's nice silhouette. Hope that answers your questions.
And theyll admire you for it. To help with that, heres your new favorite website:
http://men.style.com/gq/fashion
For general notes, have a look at "How To Build The Perfect Business Wardrobe" and for you specifically, review the "Suit Your Shape" section as well.
GQ will NEVER steer you wrong - classic and stylish wardrobe advice for any and every environment.
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