The best hats to wear with glasses

It’s getting colder and the days are getting shorter, which means winter wardrobes are at the top of our shopping list! When wrapping up warm, a lot of us will be thinking about hats. There’s no need to compromise on style and feeling warm as you brace for the cold. Here is a guide to some of the best hats to wear with glasses and how to wear them, so you can find the perfect pairing based on your preferred style.

Arlo Wolf’s Quick Tips

  1. Choose the Right Hat Style:
    • Adjustable Hats: Opt for hats with adjustable bands or straps to ensure a comfortable and secure fit without pressing too hard against the temples of your glasses.
    • Wide-Brim Hats: Wide-brim hats, such as fedoras or sun hats, can provide shade for your eyes and glasses, protecting them from direct sunlight.
  2. Mind the Size:
    • Make sure the hat is the right size for your head. Too tight or too loose can cause discomfort and affect the fit of your glasses.
  3. Hat Material:
    • Choose hats made from breathable materials like cotton or straw, especially in warmer weather. This helps prevent overheating and discomfort.
  4. Hat Position:
    • Place the hat slightly back on your head to avoid interference with the arms of your glasses. This prevents pressure on the temples, ensuring a more comfortable fit.
  5. Curved Brims:
    • If you’re wearing glasses with larger frames, consider hats with slightly curved brims. This allows the glasses to sit more comfortably on your face without interference.
  6. Adjust Glasses First:
    • Put on your glasses before the hat. This helps ensure that your glasses are positioned comfortably on your face before the hat is added.
  7. Hat with a Brim:
    • A hat with a brim can provide additional shade, reducing glare and helping with sun protection for your eyes and glasses.
  8. Avoid Tight Headwear:
    • Be cautious with tight headbands or hats that grip the head tightly. Pressure from tight headwear can cause discomfort and affect the fit of your glasses.
  9. Consider Hat-Friendly Hairstyles:
    • If your hairstyle allows, you might want to consider low-profile buns, ponytails, or hairstyles that won’t interfere with the fit of your glasses when wearing a hat.
  10. Adjustable Glasses:
    • If your glasses have adjustable nose pads or temples, make sure they are fitted to your face correctly for optimal comfort.


Perhaps one of the most versatile hats is the fedora, which people wear all year round. Fedoras can be great at keeping you warm if you find one in wool, and they go great with a variety of cold weather outfits. 

As a fedora is quite a bold statement as a hat, opt for more minimal, slightly thinner frames. Our new frame, Remi in Crystal Grey, would match a fedora perfectly. 

Baseball caps

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. 

You can pair a baseball cap with metal frames, or even pull off a really cool look with a pair of sunglasses, such as those within our Brooklyn range. If you’re curious why we’re suggesting sunglasses for colder months, you might be surprised to hear that wearing sunglasses in the winter months is actually recommended!

Beanies and bobble hats

One of the best winter looks is a beanie hat or bobble hat with glasses. These hat choices can keep you feeling snug and cosy as it gets colder, and they’re also a really stylish choice that everyone can enjoy as part of their winter look. 

Since beanies go well with the hipster and vintage looks, this winter, why not opt for a vintage-inspired pair of glasses such as Caleb in Turquoise Blue?

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

Usually a wrap or a headband is worn in summer months but these accessories can also be the perfect autumnal and winter headwear. They are comfortable and can keep your hair protected from the cold elements. That being said, a wrap or headband can cause a lot of added pressure to your head if you wear them with certain glasses, so it’s important to choose one with elasticity and flexibility to avoid cold compression and headaches. 

With the right eyewear pairing, you can pull off a really chic autumnal look. Opt for a bold statement in a glasses frame to really emphasise your hairpiece, such as Willow Eco in Red.

Find the perfect hat and glasses pairing with Arlo Wolf

When it comes to wearing a hat with glasses, choose Arlo Wolf for your eyewear. We offer everything from men’s prescription eyewear to a range of women’s glasses. We’re pretty passionate about sustainability here too, which is why we have introduced a range of unisex eco-friendly glasses.

When it comes to finding the perfect pair of glasses for your hat, you can never know for sure how your glasses will style with your hat until you see the two together for yourself. Our Try Before You Buy service allows you to try the glasses you see online before you make a decision on which frames to purchase. Give it a go today!