ONCE YOU start getting good at gift-giving, it's actually quite enjoyable. Now that you've had some practice from last holiday season, the upcoming holidays are the best time for you to perfect what you've learned about that special man in your life. However, if you still have questions, we can help too! The most helpful thing to consider before starting a search is: What would this person want that they wouldn't buy themselves? That can be anything from an investment piece to a new version of something they already have that's in desperate need of an upgrade. Or it can be an item that seems fun, but maybe isn't explicitly necessary for life. This is the opportunity for, say, a fancy new Bluetooth speaker, and not, say, printer ink.

Now, when it comes to purchasing boyfriend gifts—especially for big, end-of-year holidays—that element of fun levels up a bit. Of course, that entails a little bit of creativity, but it's only as complicated as you make it (hey, sometimes a simple gift for your man does the trick!). But be sure to take note of what catches his attention. What does he like to do in his free time? How does he like his home to feel? Does he love the feeling of a stylish new outfit, or would he rather melt than have you force him into another jacket of your choosing (again)?

Read more: Best Gifts for Girlfriends

These gentle questions are very helpful around big shopping seasons when it seems like everything is in your face but you can't sort out exactly what he'd like. Play into his hobbies (or aspirational hobbies) and get him something he'll use every day. Ahead, the 60 best boyfriend gifts to give him this year, for Christmas, his birthday, your anniversary, or any other special occasion.

Read more: Best Gifts for Men