When women accessorize with hats, they do it for beauty and style. When men see Sean Connery in a cool Panama, Michael Jackson in an angled fedora or John Wayne in a cowboy hat, though, they don’t dream of pulling off the look simply to be handsome; rather, they hope to look mysterious and powerful. If you know how to pull off a hat, you certainly could be these things. Most who reach for such an effect, though, fall short. 

At the 2014 Grammy Awards, for instance, hip-hop star Pharrell wore a full-sized fedora. As a small-headed person, though, he only managed to look thoroughly odd. The hat was so large, photographers needed to stand back to get it all in the frame. Justin Bieber has lately been sporting a hat, too — a floppy fishing hat that doesn’t make him look impressive. 

Top online fashion retailers such as The Idle Man carry plenty of hats that you could want to experiment with. While it can be hard to know exactly how to wear a hat to make yourself look stylish, practicecan help you learn. You need to pay attention to a few rules, though.

Remember that hats become a part of you

When you wear a hat, people don’t see it as a separate accessory; rather, it becomes a part of your face, your head and your entire body. When you wear a tall hat, for instance, it makes people perceive you as taller. Your newly gained height can make you look either impressive or spindly. If you wear glasses, you need to be extra careful going with a hat. With so much happening around your face, you could end up with an overly busy look.

Pick your moments

If you’re going to a club, a straw boater could work very well — you could look like Fred Astaire. It may not do you much good outside the club, though, if you plan to go to a pub or even take a walk afterwards. Most hats only make sense in specific environments.

Pick someone to copy

There are so few people wearing hats today that it can be hard for most people to have an intuitive understanding of what looks good. If you haven’t had enough exposure to hats to know how it affects your appearance, you can try to pick a great star to emulate. You could pick Sean Connery or Clark Gable, and steal their ensembles wholesale. 

Finally, it’s important to pay attention to a detail. While women’s hats tend to look good when they are perfectly new, it works differently for men. A gleaming piece fresh out of a hat box can make you look foppish. A slight amount of battering, instead, can make a hat look credible.

Alex Outlaw is a busy marketing director and editorial contributor to The Idle Man. An avid blogger, he always keeps an eye on the latest men’s fashion, culture and music news. When he finds something, he enjoys sharing it on the web. Get the latest scoop on Twitter here.