Comfort is key with pajamas, which is why At Home ($23.50- $39.95) is my favorite brand. Sure, they're completely adorable (check out the pink camo and cowboy prints), but more importantly, they're cozy and warm. Long-sleeved two-pieces can double as extra layers on snow days, and the pajama tops look swell under tees. Made from all-natural homespun cotton and manufactured in the U.S. (hence "at home"), they'll help you and your child sleep easier. Unless, of course, your child is in boycott-sleep mode, in which case you're on your own. — Rebecca Woolf

For young people who think they're as smart as old people, there's nothing more precocious than plaid. Small Paul trousers have, by far, the cutest fit of any child's pants. Their "Stewy Pants" ($39.99) are adjustable, comfortable and adorable on both girls and boys. Available in orange and blue, they're p-p-plaid to the bone — and they also run a little small, so buy a size up. — Rebecca Woolf

I'm a huge fan of hot shoes, specifically shoes I can chase my son around the neighborhood in. A little heel doesn't hurt as long as it's sturdy, right? Please say yes, because I'm obsessing over the pricey United Nude Fold Mid shoe ($243) in three hot checkered looks: red/yellow, black/black and periwinkle/blue. Adorable with jeans, skirts and even shorts, the Fold shoe is comfortable enough for stroller-pushing and fabulous enough for a sexy night out on the town. — Rebecca Woolf

"And the day came when the risk to remain tight in a bud was more painful than the risk it took to blossom." Teaching our babies to be strong and independent is one of our duties as parents. So why not wear it on their sleeves? I stumbled upon the Philosophy Shop at Café Press and was delighted by the toddler tees and onesies proudly displaying the wisdom of everyone from Leo Tolstoy and Nietzsche to Anais Nin (quoted above) and Mary Shelley ($14.99). Junior philosophers, start your engines — you can now make a statement at playgroup before you've even learned to talk. — Rebecca Woolf

Too bad these eye-catching drawers max out at a girl's size ten; several young ladies in the public eye have exhibited a rather drastic need for coverage, and Francie Pants ($15) would no doubt benefit from the exposure. The brainchild of a mother who connected with her Pre-K daughter's desire to flaunt her pretty panties at circle time, these funky boy-cut briefs subvert the shame of inadvertently revealing London and France. They blow Disney Princesses and other character-based undies out of the water with their skate-punk attitude; patterns range from Pink Graffiti to Limited Edition Greek Salad. Quick-drying and stretchy, they can even be pressed into bathing suit duty on days when Mom failed to anticipate that the sprinklers would be on. — Ayun Halliday

With a brand new baby and fifty pounds to lose, getting dressed in the morning was one of the more depressing moments of my day. Nothing fit, and I hated having to wear my maternity clothes weeks (okay, months) after giving birth. My saving grace was finding Babystyle's fashionable and extremely functional transition jeans ($68). Made with hot mamas' postpartum bodies in mind, the transition jean has a built-in belly band to slim problem areas and flatter curves. Denim is stretchy for comfort and the bootleg cut elongates legs. Oh, and they're cute. Because although comfort for a new mom is a must, style shouldn't have to fall by the waist size. Er, wayside. — Rebecca Woolf

Wear' em, cowboy! With these tasseled "Cow Pants" from Go Goose Go ($29), your little cowpoke is sure to be the most styling kid in the west. Made from the softest flannel, these pants are perfect for riding sidesaddle across the backyard or chilling at home on the range. Top them off with a kid-sized cowboy hat for a mere $6. — Rebecca Woolf

Little girl clothes can be, well, a little too girly: pinks and purples and hearts (oh my!). Why not mix up her wardrobe with something a little more rock-and-roll? These retro-inspired tattoo print skirts ($20) are handmade by Babyfairies designer Amy using vintage sewing techniques. If the tattoo print isn't your style, check out the ‘50s-style polka dots or the flea market-inspired florals. — Rebecca Woolf