How to Give Great Gifts

Writing  by Josephine D’ippolito

Artwork by Marilena Perilli

There’s a certain pleasure that comes with giving the perfect gift.  It could be a hard-to-find toy for a nephew, a first (or signed) edition for a voracious reader or a meal delivery subscription for the friend who burns toast. Whatever it is, matching the right gift with a loved one can be thrilling for the gift giver and recipient alike. Not unlike a Sunday crossword puzzle, cracking it involves thoughtful analysis, a process of elimination and even some endurance. 

It’s similar to a carefully choreographed gymnastics routine featuring the perfect combination of thought, personality and effort. It isn’t simple, and it will take time and patience to nail the landing. But with practice, the routine will get easier. And, lucky for you, we’re here to coach you through the holiday gift-giving routine. You’re welcome.

The basics 

Know who you’re buying for

The old saying about buying gifts, ‘it’s the thought that counts,’ is mostly true, as long as the thought is careful and deliberate, with the gift recipient at the top of mind. Think about their likes and dislikes, and select something that will make their life better in some way.

Think about what they love and what will spark delight. Consider their interests, passions and collections. But steer clear of items they may already own or that require a specific knowledge to purchase (a golfer or an expert baker, for example, will be very selective about the equipment they use).  

Give problem-solvers 

Are they struggling to do something? Give a gift that will help.

Do they find it challenging to decompress after a long work day? Create a relaxing playlist, paired with a nice bottle of wine or some chamomile tea. Are they always losing their keys? Get them an air tag. Do they complain about never having time for themselves? Give them free babysitting, run errands for them, make them dinner or grab pre-made dinners from their favorite deli. We’ve all got problems, and if you could solve just one of them, you would be a gift-giving superhero.

An important note about problem solving: it’s important to consider their dislikes and if you’re creating more problems with your solution. For example, if they’re not the DIY type, avoid gifts that require a lot of assembly. Similarly, someone with a black gardening thumb will not appreciate a plant that it’s ‘easy’ to take care of; it will feel like another chore for them. Or if they complain their child is too sedentary, a month of karate lessons might require them to rearrange their schedules or hire someone to get their child to or from the class, and if their child likes it, it’s now up to the parent to pay for future lessons. We’re fans of gifts, not additional stress.   

Don’t give them half a gift  (a gift card)

Unless someone specifically asks for a gift card, try to avoid them. According to USA Today, nearly half of gift cards go unused (you’re not alone – we all have a few lying around). So, about half the time, giving a gift card is the equivalent of giving no gift at all. Besides, gift cards are impersonal and don’t require any thought. An exception might be to give a gift card for an experience they will love, but in that case, don’t just give the card; book the appointment for them as part of the gift.

Be mindful / coordinate with others 

Don’t be the flashy guy with the big gift at a family gathering when everyone else is spending $50. The gift recipient might love the extravagance, but everyone else at the party will feel inept. Don’t be a jerk; stick to the budget.

Take your gift-giving to the next level

Luxurious and practical

Great gifts are luxurious, but not in the extravagant, over-the-top expensive kind of way. No Birkin bag recommendations here. Instead, they are luxurious in a unique, unexpected, not-your-everyday-purchase kind of way. And they are practical too; they are useful and can make someone’s life easier and better. A fancy face cream tried and true by the gift giver, a designer candle for the scent-snob in your life or a cashmere sweater in a favorite color or cut can be both luxurious and practical.

Personalization and monograms

While monograms sometimes feel overdone, in the right setting and for the right person, they elevate a gift from good to great. Take baby gifts: parents painstakingly choose their baby’s name, and chances are, they will love to see it featured on their baby’s swag. A Ralph Lauren monogrammed onesie is at once unique and understated. Or, for an heirloom gift they won’t grow out of, personalize a rattle or piggy bank (while you’re at it, make a first deposit with your unwanted loose change).

When personalizing gifts for a significant other, think small – a loved one will likely get a kick out of their discreetly engraved nickname on a pair of designer sunglasses (Ray-Ban and some others offer personalization on their websites).  And personalization is usually welcome on hostess gifts, too. Rather than picking up a bottle of wine on the way to an event, think ahead and order personalized cocktail napkins. Score bonus points by printing a fun poem or saying that is specific to your hostess with the mostest.

Give you to the person who says they have everything 

If they don’t need material things, give them the opportunity to spend time with you. Make a reservation and take them to a favorite restaurant. Buy tickets to see a comedian or favorite band. Pack a picnic basket and spend a few hours outdoors. Plan a day to stroll the shops in your favorite town or explore a new one. If they are avid volunteers, join them in their community service of choice. Whatever you decide, one-on-one time with your dear friend serves as a double gift for both of you.

Shop smart 

Shop local and plan ahead

There is no shortage of artists, artisans, antique shops or masterfully curated gift shops in our area. Get to know shop owners and visit them often as their inventory changes throughout the year. A piece of art available in February may be the perfect holiday gift for your in-laws, so grab it when you can. Shopping throughout the year is fun, and it will help you avoid going off the deep end in the final days of the season.

Skip the cheap souvenirs 

It’s not intuitive to buy holiday gifts when traveling, but purchasing items that are made in a specific place is a wonderful way to share a travel experience. The gift will feel special and unique because it isn’t available locally. For example, after having the best BBQ of your life in Texas, grab some sauce for the grill master on your block; when in Santa Fe, pick up handcrafted jewelry and gifts for your artsy sister-in-law. Or, when out of the country, buy gifts that are local to that region…marbled stationery in Florence, tea in London, a béret in Paris – you get the idea.  

When cash is okay

Buying for a teen or college student is often hopeless. Even the best gift-givers are often stumped. A can’t-miss idea for this group is cash presented in a fun way. Use painter’s tape to stick bills to the bottom of a shirt box so when they open the box, they will see nothing but cash. Or get even more creative and fill an empty box of chocolate (bonus: you get to empty it) with meticulously folded bills in each individual chocolate compartment. If you are crafty, use origami to fold the bills into fun shapes. Presenting cash in any way besides stuffed in an envelope is guaranteed to evoke a smile, even in the most jaded teen.

That’s a wrap

Gifts can come in every shape, size, color and price tag. While there’s no magic formula, we hope you now have more confidence in navigating this sometimes daunting task. And despite the plethora of advice given here, don’t stress. Your gift doesn’t need to change the world. It just needs to put a smile on your loved one’s face; when your gift does that, you’ve successfully nailed the landing. Well done.

This article was published in the November/December 2023 print edition of Connect to Northern Westchester.

Put the “present” in presentation

Buying a great gift and then haphazardly wrapping it is like fumbling the ball on the one-yard line. Presentation matters. Just as a beautiful dish at a restaurant prompts excitement for the meal, a creatively wrapped gift will do the same. The sky’s the limit on gift-wrapping ideas, but here are just a few to make any gift stand out:

1. Instead of a plain gift tag, use the gift recipient’s picture to identify who the gift is for. It could be a funny picture, one from their youth, or one with a cool filter, but a picture on a gift is always a crowd-pleaser.
2. Use a satin ribbon to elevate your wrapped gift. If you’re crafty, consider embroidering or stamping the gift recipient’s initials onto the ribbon.
3. If you are artsy, use plain kraft paper to wrap the gifts, then draw something on top of the gift with your favorite markers. Your artwork becomes a bonus gift.