Our Favorite Gift-Giving Strategies

A how-to guide for holiday season gifts.
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Valleybrink Road Gift Boxes 43

My biggest strategy is one that's pretty obvious, but I'm consistently surprised by how much it helps when buying gifts: I keep a running list of ideas throughout the year. Even the items that seem beyond obvious that I'd never forget, I do, which is why I have an Evernote dedicated entirely to gifts. That way, anytime I see something that my mom or best friend would like, I jot it down. Then when it's time, I buy them things they'd genuinely enjoy instead of succumbing to a last minute scramble for something they don't need. Last year for example, I surprised G with an extravagant espresso maker he'd mentioned in passing, but knew he'd treasure. - Emily

As a rule of thumb, I try to include an additional, personal touch with every gift. It can be as small as a note that says "Next coffee run is my treat!" on a mug you gift a coworker, but what I love most about this trick is that it can transform something "boring" and practical into something special—like a car phone holder (my favorite is just $19) you give with a link to your favorite Spotify playlist in celebration of a friend's new job and commute. I recently sent a girlfriend a pretty gold baking sheet as a housewarming present and included a $14.53 gift card to the gourmet grocery store near her house (the exact amount she'd need to buy all the ingredients to bake cookies). When another friend moved to Los Angeles, I gave her a city guide, with cute sticky notes pointing out places I thought she'd most enjoy, then included the pack so she could add her own. The extra addition can cost little to nothing, but goes a long way in making an impact—and their gift that much more enjoyable. - Leslie

When I'm brainstorming gift ideas, I tend to think about the gift receiver's routine and how I can make it just a little bit easier. If the person has a long car commute, I'd consider gifting them Audible to help pass the time. If he or she travels a ton, you know a CLEAR membership is in their future. If a friend is an obsessive coffee drinker, I'll look for an elevated spill-proof mug that will ensure stain-free clothes every morning (this one never spills). It's fun to give the gift of convenience and ease, and something that will remind them of how much you care about them on a day-to-day basis. - Jess

One of my favorite gift giving ideas, especially for those close family members who are hard to buy for, is to give them a custom piece of art. I personally don’t have the skills, so I keep an eye out for artists on Etsy or Instagram who will work with you to design a custom drawing, painting or print (at whatever size or price point works for your budget). You can choose any subject you like—but you can’t go wrong with children or pets. If I time things perfectly, I'll can send the final masterpiece to Framebridge for custom framing and gift wrapping, with the receiver's address as the final delivery address—saves you additional postage and a trip to the post office! - Anne

Since college, my go-to gift giving strategy has been making custom cards. I'm pretty good with Photoshop, so for close friends and family I like to make super customized cards that are both personal and hysterical. Even something as simple as Photoshopping a crown onto someone's head or a beer into their hand will get some laughs, and shows that I put some real effort in! - Kelly

Whenever possible, I try to give gifts that don't necessarily come from the store. As fun as it is to receive a product or gadget, I've noticed that the most memorable gifts I've received have been experiences. Giving an "experience gift" does not necessarily need to break the bank either—I try to gift something that will enhance a future trip or get them out of their house on a weekday night (cooking class, one night paid in an Airbnb, etc.). Although these gifts can only be used once, I find that the receivers are extremely excited to switch up their routine and celebrate the holidays even after December has passed! - Katie