How to Wear Hats with Long Hair: Stylish Tips & Tricks

Not sure how to make your hair look good when you're wearing a hat? Long hair can feel like a bit of a nuisance when you're trying to look stylish with your headgear. The wrong hairstyle can ruin the overall look or leave you looking silly whenever you take your hat off.

Thankfully, it is possible to wear a hat—and, importantly, look good—with long hair. Here, we're covering the best hat styles for longer hairstyles, as well as our own tried-and-tested tips for styling your hair under a cap.

The Best Hats for Long Hair

Some hats are just going to look better than others when your hair is long.

For instance, a beanie or a slouchy cap is a failsafe option if you want to accessorize with a hat over thick or curly hair without the dreaded squash effect. If your hair is long and loose, it'll look great under a wide-brimmed hat (this is also the perfect way to balance out your face shape).

Wondering how to wear hats with long hair in summer? You can never go wrong with a straw fedora or bucket hat to keep your hair out of your face and off your neck.

A baseball cap is another fun, casual option, especially if you're going for a more laid-back look, and the opening at the back means you've got more styling options than just "down and straight".

Styling Long Hair Under a Cap

Need more advice on how to wear a baseball hat with long hair? This is a common question, so we're dedicating a whole section to it here.

Hair Down

The good thing about baseball caps is that they usually have an opening at the back that you can tuck a low ponytail through, giving your hair a bit of style with minimal effort. But if you like to keep your long hair down, just tuck it behind your ears before you put the cap on—this'll prevent loose strands from getting in your face, especially if you have bangs.

Styling & Accessorizing

The hair down look can be a bit boring under a hat, even if it's practical. A good solution here is to use a curling iron to create some loose waves and add a bit of interest. You can also accessorize with hoop earrings, which are a perfect match for fedoras and even some baseball caps.

Getting a Good Fit

Struggling to keep your cap on? You might have a sizing issue, especially if you have thick hair. In this case, part your hair down the middle and make sure each side is lying flat first, which should prevent the cap from riding up. If you're getting a bad case of hat hair, you might need to adjust the back strap or size up so your cap isn't fitting too snugly.

Hat Hairstyles: Ponytails, Braids & Buns

You're always going to be somewhat limited when it comes to styling your hair in a ponytail or bun with a hat, but there are ways to make this look work.

Your simplest option is a ponytail—low if you're wearing any other hat aside from a cap with a gap at the back (allowing you to level up to "mid"). Forget the uber-high pony; it'll just get in the way and get squashed against your head.

Braids are the ideal solution when you're having a bad hair day or you're in a hot and flustered mood, with a serious urge to cut your hair short. You've got different style options for different hat styles. For example, if you want to cozy up in a beanie in the winter, a side braid is a great option. Or, for a cute summer hairstyle, go with a pair of loose plaits under a sun hat.

Buns are a useful hairstyle too, especially if you're short on time. But if your hair is thick, your only option is a bun that's low enough to sit under the hat. If you have short-to-medium hair, you might get away with pulling it through the back of a cap.

Comfort Tips for Wearing Hats All Day

We all want to look great when we wear a hat, but your ultimate goal should be comfort first. You ideally want to forget that you're even wearing a hat because it fits so comfortably.

If you're planning to keep your hat on for more than an hour or two, your scalp and roots might end up suffering with a bad-quality or badly-fitting hat. On a hot day, you'll absolutely want to switch to lighter fabrics and a comfortably-fitting (read: not so tight you're getting pressure headaches) band.

Be mindful of what you're using in your hair before you put a hat on. Oils and creams will have no escape under a stuffy hat, and they could end up staining the hat a weird color. If your hair starts getting itchy or your head feels sweaty, take a short break from the hat to get some much-needed air.

Finally, don't wear a hat with wet hair. Even if you've got relatively short hair, all hat styles will prevent your hair from drying properly and even cause some breakage.

So, there's the lowdown on how to wear a hat with long hair. If you're looking for a casual option to wear with a pony, check out our range of adjustable ponytail hats.