I'm not one that believes in buying a new bag just to match a new outfit or to get the latest in thing, etc. - that goes for pretty much everything. But bags do wear out and need to be replaced. When I was in junior high and high school I never had a book bag make it through a year. I was always stapling the holes and broken straps back together to make them last until the next school year.
The last one is a purse I got at Wilson's Leather sale probably 5 years ago now - it has hardly worn at all and is good for going to the store. I have a matching wallet to it somewhere as well but I'm using a different wallet right now.
The others are new, from Ross (never pay full price for a bag!) The black bag is good when I need to carry more than my wallet, phone and sunglasses but don't need to carry books or school papers, etc. It is a brand called Sasha from New York, but it feels really nice and zips shut and is a good medium size. It looks much better in person, I didn't get a good shot. It was the best looking bag in the store, trust me. :)
The top one is a Franklin Covey laptop bag. I buy laptop bags even though I don't have a laptop because they are great for my work as a teacher - I can carry binders, books, papers, calculators, and my small purse inside. Plus it has cool pockets and a little tiny wallet purse inside, etc., to help with organizing stuff. My old laptop bag, a Nine West one that was starting to wear that I also got at Ross, is a bit smaller than this one - I needed something a little larger for work and this one should last awhile I hope! (You may notice bunny ears - that is Sally the Rabbit checking out the bags - I just hope she doesn't eat them - she likes to eat things, especially bills and electrical cord LOL.)