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You have the right idea of looking towards a 5 year life in a suit, particularly if that is what you wear daily.

Most people look better in a 2 button, so that probably works for you. Try a 3 button to be sure. It really is question of your physique.

Side vents require a good cut and a good tailor or you will have a shelf on your butt. That is why most suits are sold as single vent.

Pleated vs flat front doesn't make much of a difference and I am not picky when it comes to the pants. That said, I recently picked up a 2 emergency pairs of pants from the Andover shop, one pleated, the other flat front. The flat front makes my 38" waist look not so bad. I was surprised as I have bought pleated for the last 15 years because that is mostly what has been available. The pleats provide more room in the thighs, etc, and are overall a tad more comfortable.

Unless you wear cowboy boots with your suits, have your pants cuffed.

You can't time fashion. If you could, fashion houses wouldn't make any money. Traditional clothes always look good in any time, so they are cheaper in the long run and that is why I buy them.

Good luck and look for a store with a good tailor.
 
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