16 Best Retirement Gifts to Celebrate the Milestone

Your boss has spent the better part of their career mastering their work and then passing that knowledge onto you and your coworkers. A MasterClass membership will give them an opportunity to fill their cup in other ways, learning everything from the art of pasta making to stand-up comedy and beyond—all from the comfort of their home.

Active retirees will appreciate this cool piece of wearable tech. The discreet piece of jewelry is water-resistant and incredibly lightweight but tracks all their activity—even sleep!—and monitors vital statistics like heart rate.

This new chapter is a pensive period fraught with a lot of emotions, and a journal can help the retiree sort through their thoughts, plus lay out their hopes and dreams for the future. This pick, which comes paired with a pen, is available in an array of colors and can be personalized to your liking.

Once all of the excitement dies down, there's a stark reality to face: Life is a lot different all of a sudden. This book touches on it all—finances, embracing your passions, and dealing with all the feelings (both good and bad) this new phase of life can bring—so they really can live their very best life.

Teachers dedicate their careers helping other people discover their way in this world, which is why this set of daily inspiration cards is such a great gift for an educator. Each card inside the box features Oprah's favorite quotes, prompts, and breathing exercises to help start their day on the right foot. One of the best parts? Each "task" takes just five minutes or less.

If you're looking for something small and silly for a friend or coworker, these socks will do the trick. Once they slip on this pair and kick their feet up to dive into that new novel, the message will be clear to all potential interrupters: Find someone else to help.

Your coworker may have spent ample time griping about their daily tasks, but chances are they'll eventually start to look around and wonder what to do next. This fun paint-by-numbers kit is easy enough for amateurs but might just introduce them to a new hobby once they discover the joys of painting.

With a lot more time to page through all the latest and greatest novels, an e-reader is a gift that's sure to get plenty of mileage. And it's a score for just about anyone—a teacher with a passion for learning, a traveler who wants something for the beach, or a bookish dad.

Chances are he's going to be spending some time on the links, so why not get Dad a personalized set of 12 balls, complete with 12 tees and 12 pencils—all nestled into a personalized wooden box?

A traditional board game gets a facelift that's classy enough to earn it a permanent spot on their coffee table. Good thing—they're about to have plenty of time on their hands for marathon games.

After such a long career, there's a lot to reflect on. A WiFi-enabled picture frame preloaded with snapshots through the years is a thoughtful way to memorialize a job well done. Not to mention, they'll enjoy uploading their favorite pictures from their newfound leisure time, too.

Mornings are about to become a lot slower, and your loved one will undoubtedly appreciate a super-soft pair of pajamas to help them make the most of that idle time. The long-sleeved set is made by Cozy Earth—the brand Oprah dubbed the “softest ever”—and are designed to be exceptionally breathable, complete with temperature-regulating properties. But perhaps the best part is the sage advice embroidered on the cuff that she'll spot when sipping her coffee or tea: "Live Your Best Life Every Day."

What's Mom going to do with all of that newfound time? This unique gift will help her find some purpose in those idle days of retirement. The live olive tree comes in a container that's wrapped in pretty burlap and can be placed inside or outside. She'll love learning how to tend to her new plant—plus reap the benefits of homegrown olives in time.

When you don't have to put in a request for vacation time, it's a lot easier to explore the world around you. Gift your favorite traveler this awesome carryall to make their adventures even simpler. It may look like your average weekender, but it doubles as a garment bag to keep their nicer duds polished. It even has a spot for a pair of shoes.

Without the office coffee maker to rely on for their daily cuppa, the new retiree will appreciate a classy appliance that churns out the highest-quality espresso. Plus, it's a fun way for beginners to master the art of crafting the perfect coffee beverage.

Believe it or not, give it a few weeks, and your favorite retiree might start to miss the office. This funny gag gift—a fidget toy that churns out impossibly ridiculous office jargon they're likely pretty familiar with—is the perfect reminder of why they've decided to make a graceful exit.