Like any topper, the pork pie hat has its own fashion rules, although the pork pie is such an adaptable hat that it might be better to consider them guidelines rather than rules. If you have the confidence for it, you can wear a pork pie hat with almost anything.
Casual Pork Pie Hats
The simple silhouette of a pork pie hat goes well with casual clothing. What makes a pork pie hat look more casual is its fabric; in an open-weave straw or canvas construction, it looks a bit less starched than in more formal fabrics. Prints and patterns also make a hat look more appropriate for weekends than for work days. Pair a pork pie with a button-down shirt in a vintage style or with a simple t-shirt. It's a natural match for a bowling shirt, especially if the hat and brim colors coordinate with the two tones of the shirt.
Pork Pie Hats in More Formal Styles
When you think of formal hats, you probably think of bowlers, fedoras and other shaped felt hats. Pork pie hats and felt hats have a few elements in common, but pork pies have an affable approachability that wider-brimmed fedoras may lack. That friendly appeal makes them well suited to more relaxed styles rather than extremely formal silhouettes that call for a more complex hat. A lightweight blazer with jeans and a pork pie hat is an excellent date-night option. For work wear, a pork pie is a good way to dress up long shirt sleeves and slacks when you aren't wearing a jacket. Save short sleeves for casual Fridays; even with a dapper hat, that style may be a little too relaxed for some offices.
How to Wear a Pork Pie Hat
Tipping the hat back on your head makes a pork pie hat look a little more rakish and casual. If you're slight or short, wearing your hat toward the back extends the line of your body upward rather than capping it with a flat horizontal brim. Moving the hat forward is a more businesslike look; it also tends to shorten a long face. Play around with how you wear your hat to find your best angles.