Grandpas deserve more than a "world's greatest grandpa" coffee mug. We think these personalized playing cards from Kodak Gallery ($10) are great, especially when you use a picture of the kiddos. Or for the PopPop with the amazing tales, consider the memory books from Sand Dune publishing ($15). This way he can write down all his "way back when I was your age" stories while you watch It's a Wonderful Life reruns uninterrupted. Ties are a dime a dozen, but not when they are carefully hand-embroidered with your child's artwork at Love Plus One ($50). Or maybe this is the year to spoil him rotten with a silver photo money clip from TJ and Co ($120). Grandpas love showing off the grandkids even more than we do.

If you’re stuck with the kind of mother-in-law you reluctantly have to buy a present for, try the Picasso stationery set from Anna Bella Baby ($25) featuring the artwork of your own little Picasso (or Jackson Pollack). For the MIL you wouldn't mind a drop-in visit from, step up the gift-giving with a beautiful sterling silver photo ornament from TJ and Co ($80). And if she's the kind of mother-in-law that all your friends envy, you know, who babysits your children without hesitation and doesn't critique your housekeeping skills, wardrobe, or marriage--thank her with a custom photo bag from Gina Alexander ($120-250) adorned with her favorite little grandmonkeys. And make sure to address the card "To Mom..."

Don’t forget the second but equally important half of the babymaking equation: the dads-to-be in your life. An inexpensive way to say, “hang in there, the hormonal freakouts will pass” is with Daddy Needs a Drink, ($15.64 at amazon) from author Robert Wilder. The Goodfather CD-ROM ($34.95) is a very funny primer on baby stuff that can keep even hardcore baby cynics entertained and informed. But for something really special, we can’t top the traditional route: A box of cigars from the Nat Sherman VIP selection (box of 25 starting at $119). Even if he all he does with them is pass them out to strangers in the hallway of the l&d ward.

While any mama-to-be would be happy with another layette or knit pair of booties, don't forget to pamper her! For a coworker or distant friend, we love the handmade eye pillows from Pillows for the People ($12-25) filled with stress-relieving herbs. The sentimental mama will love Tracey Clark’s beautiful Pregnancy and Baby Journals ($20 each). Get her the pair—these are the kinds she’ll actually want to fill out. Or for an extra-scrumptious treat for a friend who really needs it (or will by the third trimester), pamper her silly with a gift set of all-natural lotions and potions from VedaPure ($150). Almost good enough to eat--if only they were chocolate.

If you've got a budding Boticelli on your hands, coloring books and crayons are not the only items that will spark his or her creativity. The portable chalk art mats from Aunt Art ($15) or a cool art folio from Teacups and Tadpoles ($21) allow inspiration to strike even when you're on the move. No artist’s studio is complete without an easel – we love the classic one from Melissa and Doug ($49) that you won’t mind adorning your living room. And if your future RISD student was extra extra good this year, let her know it with the Chalk Table Set from Sparkability ($250). We're strongly in favor of fostering creativity that doesn't lead to any wall repainting around the home.

While they do grow up faster than we’d like, there’s no reason you can’t appease her fashion-forward sensibility while still staying (ahem) somewhat age-appropriate. No belly tees, we promise. The Carrotbox has a terrific selection of fun lucite rings that girls will love--we especially dig the carved flowers ($16-18). No tween fashionplate will be able to resist a trio of funky handmade headbands from ElisaLou Designs (3 for $30). And the awesome pink Zoe handbag ($50 at Pixel Girl Shop) will certainly set her apart from the kiddies in her class still stuck on Bratz and Barbies. Or one can hope.

We can’t tell you how to avoid the politics inherent in doling out goodies to your mom clan, but we can suggest a few items that they’ll want to bicker over. For an inexpensive little trifle, we love the funky makeup bags from Queen Puff Puff ($14). The bold, Asian inspired boxed notecards ($19-45) from Joy by Mel Lim are an appropriate thank you for the mom who cleaned up after your kid the day he came down with the stomach virus. (And they can be personalized if you order soon!) And for the mom worthy of sainthood—you know, the one who always remembers to bring the alcohol? Make sure to hook her up right this year with the Koka shoulder tote from Lotta Jansdotter ($58). Just make sure you give it to her out of the view of the other moms--and then swear her to secrecy.

Not just any gift will do for your best friend, especially the type who puts up with the daily toddler-tantrum laced phone conversations without a single complaint. For a gift in the reasonable range, try one of the handmade fabric covered journals from Pixel Girl Shop ($34) and give it to her over coffee--just the two of you. If she deserves something a little more indulgent--like she plays Play-Doh with the kids while you put your feet up--the beautiful washi paper pendants ($75) from Blend Creations will make her eyes light up. And if she saves your butt on a regular basis, honor her with something she covets but might not buy herself, like a Kristin Kahle belt handmade from vintage fabric ($135-150). That's what friends are for, right?

If you’re lucky enough to have a reliable, responsible young sitter who doesn’t make out with her boyfriend on your couch (or at least not on your bed), you owe her big time. The one-of-a-kind acrylic kimono rings from The Carrotbox ($16) fit nearly any young girl’s style. For a little more, you can create a custom beauty gift pouch ($23.50-32.50) full of yummy natural soaps, body butters or lip glosses from Mi-Spa artisanal skincare. But for the sitter who’s like another member of your family, thank her with Peggy Li’s Peace Tag necklace ($59). That is, if you really want to insure you can continue to indulge those last minute Saturday night movie cravings.

This is the one time of year you can really tell your children’s teachers thanks for dealing with…er, educating your little angel. Herb+Ginger sells delicious Rooibos Teas ($8 and up) along with an inexpensive set of fillable tea bags ($8). You can’t go wrong with the botanical notecards from Egg Press ($25)—if she’s that cool a teacher, she’ll surely have lots of thank you notes to write this holiday. And for really, truly invaluable teacher, the one you’ve petitioned the schoolboard to teach your kid all the way through high school, the chalkboard pendant from Elsewares $70) is so awesome, it’s practically a bribe. Not that you’d ever stoop to something like that.

PS If your beloved educator is a man, skip the pendant and instead check out Elsewares’ Personalized Typekey Pen ($72). Anything but a paperweight!

It’s perfectly natural for girls to go through a princess phase, even if their moms are cringing with every shiny tiara request. Fortunately we’ve got a few gift ideas you can both live with. The Cupcake Mini Stationery and Stickers Set ($8 at Pixel Girl Shop) will let her thank grandma for the ballerina outfit with delicious, sparkly goodness. We love Dolca’s collection of clothing—especially The Friend Dress ($32 at the White Balloon) which is as pink as pink gets while staying clear of fairy dust motifs. Accessorize with a pair of felt flower hair clips from Giddy Giddy ($16 for 2 at Mahar Dry Goods). And for a super splurge for that very special girlie girl, we love the playtents from Tee Pee for Me which can be ordered in a dainty rose petal fabric ($288). Because even little princesses need a place to daydream about their royal escapades.

If you’ve already exhausted every plastic dinosaur toy out there, we’ve come up with a few Mesozoic-era options that you might have missed. You can’t beat your kid’s name turned into an actual dinosaur then printed on a cool custom t-shirt from Alex and Jett ($18). For a few more bucks, check out the Dino backpack from Little Packrats($40) or the exquisite wooden marionettes which double as a decoration and then a toy ($38 at Mahar Dry Goods). For the mini dino lover you love best of all, try a wooden Dino Rocker ($100) and let him play Jurassic Park III all day long.

There’s nothing like experiencing New York City over the holidays with your children, even if it’s just from your living room in Columbus. Joanne Dugan’s alphabet book ABC NYC ($10.61 at amazon) is a vivid introduction to bagels, manholes and skyscrapers. The Serendipity Frozen Hot Chocolate Gift Box ($25) lets you recreate right from home, the very drink that has kids begging to return to the big apple every year. But if you’re really committed to keeping NYC in your heart long after the Rock Center tree’s come down, deck your child’s walls with the gallery quality NYC alphabet C-print ($300 and up) from Sparkability. It costs less than taking the family to the Radio City Christmas show and lasts longer too.

Stay out of the dollar bin at the big box store. Here's a selection of great items, none of them more than 10 bucks. And you're not likely to get them regifted back to you next year.

Pixel Girl Shop
Pink Starbust Hairclips, Cherry Blossom Cell Phone Charms, Vinyl Skull and Crossbones Keychain

Uncommon Goods
Bike Chain Bottle Opener, Coal Gum, Genius Decks for Kids, Bag of Pewter Hearts

Copacetique
Tiny Animals Pencil Case, Leafy Luggage Tag, Bonnet Girl Gingham Pouch, Turntable Wrist Cuffs

Modern Tots
Kids Chopsticks, Mini Radio, Toothbrush Clips, Pocket Paint Set

The Perfect Card
Haute Note
Joy by Mel Lim
Basically Cards
Fabulous Stationery
Egg Press
Letterspace Paper
Enduring Notions
Write Now Notes
Groovy Paper

Wrap it Up
Olive Paper
Joy By Mel Lim

Tag It
Shades of Violet
Amy Smyth Made It
The Small Object
DeMarco Designs
Erin Condren Design

Stuff This
Fadiddle Custom Stockings
Mahar Dry Goods