The Cool Aunt’s Holiday Gift Guide

Before I was a mom, I was an aunt. There are a lot of great things about being an aunt. You get to do things like teach your nephew about candy and feed him bowls of whipped cream for dinner. You can play with him for an hour and then hand him off when it’s time for a diaper change because hey, he’s not your kid. And you can buy him really impractical gifts because you don’t have to think about how it will wear or what special care it requires or how many hours of daycare it could have paid for. (I’m told this all works for nieces, too, but I’m just speaking from my personal experience here.)

Now that I am a mom, I get to see my sister-in-law take on the role of The Cool Aunt. She is the source of the Bitty Baby (and the Bitty Baby’s fall coat, picnic basket, snowsuit, tiny pairs of glasses, and grocery shopping set), the first pair of Doc Martens, and a variety of adorable full-price toddler outfits from brands I’ve never heard of.

With all the Cool Aunts in mind, I’ve put together a roundup of a few of the items I’d be considering this year if I were The Cool Aunt to a hip toddler. I’ve also got them tracked over here on this Pinterest board, and I’ll keep adding to it throughout the season.

Let’s be really, really clear: These gifts are mostly not practical. They are likely not smart buys. And they are absolutely not wise uses of your hard-earned dollars… If you are a parent. Cool Aunts (and Cool Uncles!) with disposable income, these picks are all about you and your fancy-free ability to buy adorable things just because they’re adorable.

Happy shopping, Cool Aunts!

Andy & Evan Airplane Pullover Sweater
Size 2T-7Y
Nieman Marcus, $46

Andy & Evan Airplane Pullover

How cute is this little sweater with the little biplane? And I’m a sucker for elbow patches. Would pair nicely with some tiny khakis or plaid pants (or maybe a little kilt?).

Ralph Lauren Fair Isle Fleece Sweatpant
Size 2T-6x
Ralph Lauren, $45

Ralph Lauren Fair Isle Fleece Sweatpant

SWANTS. I’ve made no secret of my love for them. These up the comfort factor by masquerading as swants when they are, in fact, sweatpants. Sneaky sneaky, Ralph Lauren.

Burberry Haidee Check A-Line Dress
Size 4-14
Neiman Marcus, $250

Burberry Haidee Check A-Line Dress

Ah, there’s nothing more classic than a basic Burberry check. Sadly, there are few classic basics more expensive. This is the kind of thing I could only justify buying if I had, like, four daughters who were all going to wear it as a hand-me-down. So it’s the perfect pick for the chic Cool Aunt.

Zoe Faux Fur Capelet
Size 2-6x
Neiman Marcus, $90

Zoe Faux Fur Capelet

My kid has about as much patience for capes as she has for my singing. But a more tolerant child would look really adorable wearing this in holiday photos.

Ralph Lauren Childrenswear Shawl-Collar Pullover Sweater
Size 2T-7
Neiman Marcus, $95

Ralph Lauren Childrenswear Shawl-Collar Pullover Sweater

This is the kind of sweater worn by a little boy in oxblood loafers passing a tray of holiday cookies in a Martha Stewart Living spread. With good looks like that, who needs to save for college?

Return to Tiffany Double Heart Pendant
Tiffany, $250

Return to Tiffany double heart pendant

Yeah, this is one of those gifts that her mom will probably put away on a high shelf until she’s older. The good news is, she’ll still be able to wear it then! Bonus points for extended wear and classic style.

Milly Minis Sequin Cap-Sleeve Shift Dress
Size 4-7
Neiman Marcus, $165

Milly Minis Sequin Cap-Sleeve Dress

I had the 1980s version of this dress as a child, which involved a black velvet drop-waist bodice and a white-and-black polka-dot taffeta skirt. It was equally as chic in ’80s terms, which is to say: This one is much better.

Andy & Evan Windowpane Check Two-Button Blazer
Size 2T-7Y
Neiman Marcus, $74

Andy & Even Windowpane Check Two-Button Blazer

For the little Warbler in your life. (Elbow patches! I die.)

Kate Spade Leopard Print Faux Fur Vest
Size 2-6
Neiman Marcus, $84

Kate Spade Leopard Faux Fur Vest

Serious question: Why would anyone even make an item of toddler clothing with a hood and not put ears on it? This vest almost makes up for some very overpriced earrings I got from Kate Spade a few years ago that turned out to be very cheap plastic.

Almost.

Andy & Evan Cotton Hound V-Neck Pullover Sweater
Size 2T-7Y
Neiman Marcus, $46

Andy & Evan Cotton Hound V-Neck Pullover

To begin with, there’s the dog. Wearing a bowtie. Then you notice it also has a monocle. And then they cap it all off with elbow patches.

Kate Spade Girls’ Scout Glitter Crossbody
Bloomingdales, $128

Kate Spade New York Girls' Scout Glitter Crossbody

My kid has a purse kind of like this, except that it’s blue not glittery and I got it on clearance at Charming Charlie, and she occasionally picks it up and shoves vintage Fisher Price Little People in it before kicking it into a corner. That said, if she were my niece instead of my daughter, I would be sorely tempted to buy her this tiny Kate Spade bag.

Milly Minis Blaire Feather-Skirt Sleeveless Dress
Size 4-7
Neiman Marcus, $275

Milly Minis Blaire Ostrich Feather Dress

Oh, hey, is that Blue Ivy Carter? Nope, it’s your niece, but the confusion is understandable considering they obviously share a stylist. Lest you think Milly would cheap out on you, let me assure you — those are real ostrich feathers. Audrey Hepburn, eat your heart out.

Find more Cool Aunt picks at The Cool Aunt’s Gift Guide on Pinterest!

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