I also can't choose one over the other. I have 2 of each and both styles rock! (Putty and Teal Lindsays and Red Patent and Pealized Green Peytons) The Lindsay is more dressy IMO, but the Peyton holds more. Also, the Peyton is more comfortable to carry on my shoulder. It can be done with the Lindsay but the handles are shorter and makes my arm stick out, so for me Lindsay is an arm crook or hand carried purse. I guess for comfort and ease of being able to put everything plus the kitchen sink in it - Peyton wins. (plus add in the yummy Legacy lining!) But, when I want more style then Lindsay wins. I do end up using Peyton more for real every day life needs, and pull out a Lindsay only for special occasions. Also, Lindsay is heavier than Peyton if that makes a difference.