Moms (and frankly, all of us!) seek comfort in everyday wear, and Alessandra Ambrosio proves that you don't have to sacrifice style to keep up with the kiddos. On a trip to the farm with her son, she sports an easy graphic tee and jeans, but the fedora and riding boots are the perfect touches of flair without going overboard. Keep a lightweight utility jacket handy by effortlessly tying it around your waist!

There's something so envious about Sienna Miller's style, and this time around it's her gorgeous bomber jacket. Much can be done with such a versatile piece, but when you're going for comfort, the boyfriend jeans & sweater combo is a no-brainer. Finish off with some cool combat boots and you'll strike the perfect balance between causal and edgy like Sienna does!