Fabrics also play into a hat being vintage such as being faded, perhaps with a little wear and tear and even certain colorways. That being said, hold on to your hats and pass them down so the next generation can relive your glory days just as you are with someone else’s classic vintage cap.

Hopefully, you now have a better understanding of different hats and ways to style them. The biggest advice I have is to just do what feels right and be you, regardless of what is considered “trendy” or “fashionable.” Being yourself and being confident is your biggest advantage to pulling off any of these looks.

10. Western

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Surprisingly (to me anyway) there is a variety of western hat styles – the derby, the pinched front, the gambler, and the cattleman – each with their own unique features. The best way to decide which one is right for you? Try them all! And don’t worry if you’re a city boy. Did you know that John Stetson (the originator of the famous Stetson cowboy hat) was born in New Jersey, not out on the farms in Oklahoma or in Texas, which would have been my guess. 

These hats are available in different fabrics, embellishments, and sizes. As far as styling goes, you can’t go wrong with a plain white t-shirt and jeans. Solids, plaids, flannels, and sweaters also work. Just try to avoid anything that screams “COWBOY!” Unless that’s what you are going for or are headed to a costume party.

11. Winter

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Beanies, also called stocking caps or sock hats, are the most common winter hats because they are the most casual, practical, and versatile. Made for colder weather, beanies are also a favorite amongst anyone looking to just throw on an easy hat. I wouldn’t suggest throwing one on in the heat of summer but I’ve seen it before and didn’t bat an eye.