Baseball caps can be worn all year round and are great if you have shorter hair. In the winter months, a lot of us wear baseball caps because they are a more flexible option than other types of hat, and are less likely to make our heads itch. Go get yourself a tightly-woven straw fedora to throw in your beach bag and laze by the pool. It looks super cute with anything from a pair of boyfriend jeans and an oversized shirt to a more refined maxi-dress. Add a bit of a color pop with a fun bright ribbon around it.

The typical bowler hat goes well with rounded vintage inspired glasses , like this glamorous metal wire frame pair of John Lennon inspired glasses . 7. Beret

Cable Knit – Cable knit beanies are created by a knitting technique that crosses the vertical stripes over each other for a braided pattern. Cable patterns typically result in a dense, warm beanie. Made from a soft and cozy yarn blend of polyester fleece and wool, this beanie feels comfortable against our skin and is easy to care for, while providing excellent insulation for our head and ears, against both the cold and the wind. Its classic design is versatile enough to wear with almost any winter outfit. The beanie is available in a range of colors, allowing you to choose one that matches your personal style. We also found that it works well during high-intensity activities like hiking or jogging since it’ll stay on our heads. Naadam is on a mission to make the “world’s fairest cashmere” by cutting out the middlemen who stand between herders and retailers. The result is a slew of top-quality, sustainable knitwear for a fraction of the price you’d pay elsewhere that our tester found to be heavenly soft. If our word alone isn’t enough, consider that thousands of satisfied customers have given this beanie a 5-star rating. That’s a win-win for everyone—well, except those middlemen. Wear a plain neutral Panama hat with dark lenses and patterned frames . If you’re not ready for an all-over pattern, decorated lens arms will suffice. Animal prints are huge once again, and this time, it’s even amongst men! Shop for the perfect Panama hat glasses at Vint & York now. 2. Trilby hat

So how can you wear your hat and glasses together and pull off the look while keeping it looking effortless? This style is for the man who likes to dress up, but with a bit of a hipster edge . The pork pie hat man is a man who favors blazers, skinny chinos, and a pair of classic boat shoes. The pork pie hat is incredibly versatile, and it pairs well with just about any style of glasses you choose. Keep the hipster vibe going by wearing your pork pie hat with glasses featuring a browline frame. The Astor eyeglasses – Get yours here !

Similarly, another knitted variation of the beanie is the bobble hat, which looks great with a range of glasses. When you’re thinking about how to wear a bobble hat with glasses, look for a pair that’s minimalist but chic, such as Chandler in Crystal . Headbands or wraps The only thing is that the acrylic isn’t too heavy-duty at insulation, so this beanie probably won’t accompany you to the North Pole. Still, for daily urban jaunts, Carhartt’s beanie is ready for anything.