The Trickiest Gifting Dilemmas & How To Solve Them

Checking your mom and BFF off the list is easy. You know what they like, head to the store (or click on the website), and that’s it. The others? Well, that’s a different story. Finding presents for the trickiest folks in your crew can be a nightmare. Who has the time or energy to search (and search) for something that they'll end up shooting you the look over anyway? #Fail. So, to avoid a full-on breakdown this holiday season, we’re arming you with the best gifts for your difficult peeps.
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For The S.O.’s Mom
Whether you just started dating or have been together for a zillion years, shopping for your partner's mom is always a challenge. To avoid judgment when she opens her gift, go for something she has to like — like a pretty pair of earrings. If you still don't have her taste down (seriously, why does it always change?), go for a crowd-pleasing stone like aquamarine.
Melissa Joy Manning Emerald Cut Aquamarine Drop Earrings, $90, available at Melissa Joy Manning.
For The Impossible Boss
A boss is quite possibly the worst person to shop for. What's appropriate? And, when is it too much? Does it look like you're sucking up? Bah. Give her something nice, but not too elaborate. Make sure it's universally appealing, too. If she doesn't like it, she'll at least toss it on her bookshelf and remember how thoughtful you are every time she walks by it.
Assouline Vintage Cars by Ken Gross, $95, available at Assouline.
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For The Person Who Hates Stuff
Everyone's got that friend who hates clutter and eschews the worldly possessions we hold so dear. But, let's see them try to resist this tablet that renders every other device obsolete.
Microsoft Surface Pro 3, $799, available at Microsoft .
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For The Oh-So-Fancy Friend
She already has everything — like the latest Proenza dress and Prada pumps — but you can't show up to your annual gift-giving shindig empty-handed. While she clearly has clutches galore, you can never have too many, right? A functional pouch with subtle, yet eye-catching details will seamlessly fit into her collection.
Clare V. Flat Clutch, $198, available at Clare V.
For The Two-Year-Old Nephew You Just Met
Your brother lives 3,000 miles away and because of [insert semi-valid excuse here] you haven't actually met his child yet. Oops. Well, the day's finally arrived. But, you don't know his vibe. Is he a truck kid? A train boy? More into Barbies? Keep it safe with an adorable plush toy. What's not to love?
Jellycat Vivi Crocodile Plush, $22, available at Barneys New York.
For The Hard-To-Please Teenage Sister
Nothing's good enough for this lady. No matter what you give her, it's just never right. That's where the makeup set comes in. No matter how her style preferences change, these neutral shades go with everything. So, the Bobbi Brown set is essentially a no-brainer.
Bobbi Brown Mini Lip & Eye Palette, $30, available at Bobbi Brown.
For The Boyfriend Who Never Wants Anything
The typical response when you ask your boyfriend what he wants? "Nothing." And, you know that's not actually true. So, go for something he actually needs, like a pair of waterproof boots to conquer Mother Nature. Sure, he says his sneakers work for everything, but, c'mon, dude.
Ugg Australia Hannen Boots, $230, available at Ugg Australia.