Oh, Amanda—I sooooooo understand where you’re coming from. I mourn the loss of my old handbags and even though my son is two as well, I still am having the trouble transitioning back to the purse (he just needs so much ….stuff!). There are, however, some great, roomy options that should make “the switch” effortless. My favorite: Kooba’s Aram Multi Stitch Shopper, which  offers a magnetic snap closure for easy in and out, exterior side pockets—perfect for holding sippy cups. It also features an interior zip and wall pockets to keep your keys, wallet and phone free from stray Goldfish crumbs. Because it’s made from patent leather (which is incredibly hot right now—bonus points!), it will repel accidental spills better than traditional leather or fabric (one quick tip I learned from my pal Alison: if you’re gonna stash a cup inside your bag, keep it sealed in a quart-sized Ziploc bag, just in case). The best part: should you decide after testing it out that you’re not yet switch-ready, you’ll still be left with a really cute bag you’d probably want anyway. The bag can be purchased at Nordstrom stores and www.nordstrom.com for $595.