When it comes to finding the perfect pair of jeans comfort is everything. You should ideally be looking for the perfect mix of style and comfort. Jeans need to look good but more importantly feel good. When it comes to selecting a pair I think it is always best to go to multiple stores that specialize in denim and try on a few pairs until you find what works for you. One of the important aspects of a pair of jeans is whether or not they will work with the rest of your wardrobe. Your choice of shoes can dictate how wide you want the ankle of your jeans to be cut.
Boot cut jeans are jeans that fit normally through the rest of the jean, but the ankle of the jean is cut wider to allow them to sit lower and more comfortable over a pair of shoes. Tapered jeans are cut with a slimmer ankle that is tighter as the leg goes down. If you are looking for a more comfortable look that is cut to be worn with many of today's shoe styles you may want to look into boot cut jeans. Since jeans are becoming more acceptable in the business world they are often being worn with dressier shoes and need to be a little wider to allow for the shoes to look natural with the jeans. Tapered jeans tend to be more traditional looking and are popular especially in women. Most men's jeans are being cut a little wider to sit more comfortably without feeling constricted. Some men still choose to go with tapered jeans if they often wear taller boots.
Whatever your decision make sure to try on several pairs from several different companies before making your decision. Remember to think about your wardrobe when making your decision.