Investing in a Designer Bag

I just bought a MICHAEL by Michael Kors bag, a black Berkley E/W Shoulder Flap, and now I'm starting to wonder if I spent way too much money on this one. It's my first splurge on a designer bag... I also got it on sale for $175, the regular price is $298. I don't know if I'm overthinking this or what. Should I return it, and find a cheaper replacement? In part, I like knowing that I have a designer bag, but at the same time I'm kind of regretting it. I also am thinking that a designer bag has better quality, and it will last me longer. I'm so confused. This is a real bag dilemma. Here's a picture of it below:

The perfect red leather bag

I have two red leather bags, and I’d love to love one or the other, but I use both. One is larger, and my mother bought it for me on a trip to Venice. It’s downfall is the closure on the top—a large fold-over flap, which means I have to take it off my shoulder whenever I need to grab anything, unless I tuck the flap inside, which leaves a fitting exposed. The other is smaller, and is an alligator-textured leather. It’s downfall is that it’s just too small for anything more than going to church.

The mother bag

I’m now a mom, and I end up switching back and forth between my diaper bag and my work bag. I have to shuffle my wallet, my phone, my business cards (as a mom, I can still promote my business, can't I?) and my makeup bag. After a few months, I began gathering these items together in a small clutch, which I could shift from bag to bag. And, when I was just dashing in someplace, I could just grab the clutch out of the bigger bag and take it (and the baby) with me. After reading this site, however, I feel I must be committing a fashion faux pas by using my clutch during the day. What can I replace it with?