Your Holiday Shopping Guide: How to Find Clothes He’ll Actually Wear

Holiday Gifts for HimUnless you're allied with an especially sartorially savvy gentleman, getting him to express an interest in clothing is akin to tearing him away from the TV during a football game. There's no doubt, however, that some gentle tweaking in the wardrobe department will benefit him by leaps and bounds. He'll look and feel great, especially if he's in something that he truly enjoys wearing. How to find those elusive most-wanted items when he's not exactly shouting it from the rooftops? Consider these tips:

1. Keep it simple. There's no need to invest in a slew of crazy-loud pieces just for the sake of changing things up. Try a subtle approach, like introducing a few new polo shirts or easy cardigans to his wardrobe. The key is to stick with pieces that you know he already wears and loves and expand from there.

2. Know his favorites. If he's obsessed with a particular sports team or athletic brand or is devoted to his college alma mater, treat him to a few key pieces that represent the team or school best. There's no doubt those sweatshirts and T-shirts will get plenty of action on and off season.

3. Find something “suit”able. There's value in a phenomenal suit—one that really shows off his best assets and makes him look the picture of polished perfection. Not only is it the corporate ideal, it also comes in handy in other situations, be it a highly anticipated dinner date or a job interview.

4. Understand his style. If he's never shown an interest in leather jackets and black boots before, he's probably not going to start now. Embrace what makes his style so important to him, whether it's his obsession with comfy sweatpants or his affinity for starchy white dress shirts, and follow that lead.

5. Complement his style. In the same vein, it's easy to choose complementary pieces that up his style game just enough to make a little difference. Those sharp white dress shirts look even more handsome with a pair of classic cufflinks. That pair of sweatpants could use an equally comfortable fleece pullover. Taking things to the next level couldn't be simpler.

6. Go for classic. When in doubt, timeless is always the way to go. Something as pristine as a pair of smart Dockers® khaki pants or a sharp button-down shirt will never steer him wrong, simply because these are traditional pieces that last and last. They'll see him through almost anything, and it's hard to resist that kind of versatility.