Elana! Don't get me started on handbags. They're my kryptonite, and Hubs does not appreciate giving up yet more shelf space for the collection (or the credit card bill said collection produces), but I do hear ya' on needing your hands free at all times with three babes in the mix, and my third isn't even walking (much less running) yet.
There just seem to be a lot of gyroscopic moving parts these days--once we finally manage to wrangle ourselves into the car, I find myself breathlessly counting them OCD-style (1-2-3, 1-2-3, 1-2-3, "Henry, is the baby in the car with us?"). But it just so happens that I do believe something as simple as a handbag can help establish a modicum of sanity, even during these crazy days of early child rearing.
$438 - couture.zappos.com
$275 - bluefly.com
$75 - asos.com
$296 - zappos.com
$182 - asos.com
$555 - couture.zappos.com
$95 - bigbuddha.com
$200 - asos.com
$27 - kohls.com
$95 - bigbuddha.com
$66 - asos.com
$50 - zappos.com
$40 - target.com
$168 - zappos.com
Happily, I've found a bunch of affordable (and some not-so affordable), yummy cross-body handbag options, and it came as a shock to me that my hands down fav is a $40 find from Target. I am seriously crushing on the Chocolate New York Satchel ($40). The structured, ladylike satchel handbag silhouette is going strong and still feels fresh. I'd love to offset the prim vibe with army green (Houlihans, an anorak or sleeveless military shirt), or play it up with a full skirt and espadrilles.
Check out how ASOS styled (another big crush) the Cambridge Satchel and the Color Block Smart Bag (love!):
My other fav, the Motif-56 M-Dori ($168 on sale at Zappos from $240), isn't quite as affordable, but has fab details that make it well worth the investment. I'd wear this with anything from printed shorts to a tie-dye kaftan, a black maxi, or use it to add (a lot) of interest to a standard t-shirt and jeans/cutoffs outfit.
A close runner up is the Big Buddha J-Courtney ($95, use Big Buddha coupon code BAG20 for 20% off). The woven details, vintage Aztec print and huge interior make it a winner as a diaper bag replacement and will rock with a tiered maxi skirt and denim vest.
All of the picks should be large enough to carry the essentials without feeling over-stuffed. If you're in a city and walking all day long, I would avoid carrying heavy toys, water bottles or books and throw those in your stroller basket instead for comfort.
Hope this helps, Elana--thank you for your kind words and for writing in!