Sometimes I think one of the trickiest things about dressing well when raising kids is their — for lack of a better term — capacity for destruction (sartorially-speaking).  My list is long and growing: the Thomas Pink shirtdress, purchased in London and worn everywhere, forever stained when I leaked through it while nursing LittleMan before work one morning; the Marc Jacobs aviator sunglasses Babygirl mangled during an early dinner at a local pub; the Banana Republic wide-wale white sailor corduroys that LittleMan smeared with chocolate-covered hands; the fact that my dry cleaner can pay for a trip to Barbados with the revenue generated by Babygirl’s first spit-up-infused six months.

For a day off with the kids, bright colors (the double-strap Swatches are so cute you could wear two!) and playful touches (ponies on your pants, hightops, fingerless gloves) keep the mood light.  If you need something a little on the sleeker side, the James Perse cozies are elevated by an elegant sweater/cape, tough cuff and glam gloves that break a few rules (thank you, Brian Atwood) but never the bank (merci, Target!).

– Jaime