5 Common Gift-Giving Dilemmas, Solved

In theory, buying presents for your friends and family should be fun — unless you totally hate shopping or happiness or Christmas, or whatever, in which case, go away, you Scrooge. And yet, almost without fail, the holidays come along, and suddenly you find yourself facing a whole slew of gift-giving dilemmas: what do you get your co-worker you've only spoken two words to? Should you get your boss a present? What about your dad, who buys himself absolutely freaking everything? Will your sister hate you forever if you get her a $20 iTunes card and call it a day? You're a week away from the big day, you're scrambling to cross things off your to-do list, and the idea of going to the mall and facing the crowds of holi-dazed shoppers all frantically on the prowl for last minute gifts makes you want to curl up in your Grinch cave, down a couple glasses of wine, and just pass out until January 2 finally rolls around, and then you can pretend like the whole month of December didn't happen. Even when you have the best intentions, gift giving can be tough. Oh yeah. I totally get it.

And so does Julie Kenney, gifting expert to the stars. Kenney has built an entire career around giving world-class gifts. Her company, Jewels and Pinstripes, specializes in creating one-of-a-kind gift bags to hand out at high profile events, and her VIP picks have ended up in the hands of A-listers like Angelina Jolie, Katie Holmes, and Madonna — seriously, she knows what's up. Still looking to pick up a few last minute gifts? Feeling completely out of ideas? Kenney has you covered. She's teaming up with T.J.Maxx, Marshalls, and Homegoods to give out all-star advice regarding all your gift-giving needs. We asked her for help with five common conundrums, and she generously delivered. Here's what she had to say.

1. What can you do to make a gift feel more personal?

Personalized Necklace, $105, Max&Chloe

In a perfect world, you'd be able to put hours of thought into each and every holiday gift you send out this year. (In a perfect world, you'd probably also have Ryan Gosling helping you gift wrap everything.) But because time is scarce — especially around this time of year — sometimes the best you can do is just run to the store and pick up the first thing that speaks to you. Which is fine, so long as you make sure to include a few personal, finishing touches. "Get a blanket monogrammed at a local embroidery shop, write a handwritten note on the back of your gift, or take your gift out of it's original packaging and place it inside an organizational basket or beautiful gift box." Kenney suggests. Love the idea of going the monogrammed route? A pretty necklace stamped with an initial is simple, yet thoughtful. Get this one from Max and Chloe.

2. How do you shop for someone who already has everything?

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There's always one person on your list who is absolutely impossible to shop for, but just take a deep breath, OK? "Choose a product that isn't on your recipient's staple list," Kenney says. "Go for a brightly colored handbag, a newly-released beauty product, patterned shoes, flavored tea or coffee or even limited edition holiday decor." And if you're really stuck for ideas? Go someplace you know will have a little bit of everything. "When I’m stumped for a gift, I visit places that carry a wide variety of items in one location. I love T.J.Maxx, Marshalls, and HomeGoods for my holiday gifting because they provide inspiration for my whole shopping list all at once with their many different departments," she says. Another great tip? "You can also see if they have a Pinterest board to get some additional ideas." We're pretty obsessed with these sparkly clutches at Marshalls. Who doesn't want a little glitz around the holidays?

3. What should you buy your boss?

No but seriously, what do you buy for you boss? Something funny? Something they'll actually use? Kenney suggests choosing a gift that relates to your boss' hobbies. You work with this person every day — even if you two aren't the best of friends, chances are you still know a little something about their interests. Here's her advice: "Go practical if you don't know them very well and funny only if they have a similar sense of humor. Pick a price point that fits your budget. You want to celebrate and thank your boss for a great year, but there is no need to go into debt because of it." You can't go wrong with some cute, personalized stationery, like this set on Etsy.

4. How do you go Christmas shopping for someone you barely know?

So you've been dragged into an office-wide Secret Santa gift exchange, and you end up drawing the name of someone you've met maybe once, last year, at your last company holiday party. Now what? "If you don't know your office coworker very well, purchase items that will accessorize and brighten their day while at the office," Kenney says. Her favorite picks include a patterned lunch bag, a pretty scarf (like this festive plaid pick from Forever 21) or cardigan, or cute desk and office supplies.

5. Any advice for shoppers who put off gift buying until the last minute?

First thing's first — know that you're not alone. "Even the most organized gifter still buys a few last minute gifts!" Kenney says. Need something that seems totally planned and well-thought out in a pinch? Remember this word: Presentation. “Since you are pressed for time, go with beautiful gift boxes or gift bags instead of trying to wrap your gifts. It will save you a ton of time, and you can use that time to handwrite gift tags for an extra special touch." We love these shiny, sparkly bags Paper Source's Glitzy Gold collection. You know that anything wrapped in glitter is going to be a good time.

Image: Fotolia; Max and Chloe; Marshalls; Etsy; Forever21; Paper Source