How to Wear a Hat with Long Hair (Woman's Guide)

Hey hotties,

Admit it, we’ve all had our bad hair days. You might’ve woken up late and needed a quick hairstyle, or, like me, you live in the atrocious Florida heat and can’t stand having your hair stick to the back of your neck. Either way, I’m positive that at some point in time, you’ve needed, or just simply wanted, a hat-day. 

Unfortunately, you might be like some of my friends. A lot of them won’t pick up a hat because they feel like it’s too difficult to style properly with their hair, especially my friends with long hair. Even more so for my friends with long textured hair. After all, it’s hard to beat all my pixie cut dream queen friends who can rock the hat look with little to no effort. 

You might not guess this, but I originally had a hard time styling this look. It either looked like I tried way too hard with a greasy slick back, or that I didn’t try at all and ended up looking like I just woke up from a 48-hour well-needed sleep after climbing Mount Everest; there was no in between. Nevertheless, my loves, I’m here to tell you that there is absolutely a way to look hot in a dad hat; you just have to know how to style your hair properly.

I mean, let’s be honest, that’s why you’re here. You don’t need my whole life story. Even though I’d love to sit down with you guys, drink tea, and over-share the last 26 years of my existence, I’m here to help you learn how to wear a hat with long hair so that you don’t end up looking like you escaped death. I say that in the nicest way possible.

How To Wear a Hat with Long Hair: Style it Like one of These!

The High Ponytail

This is a classic. If you want to wear a cute ponytail with your dad hat without looking like one of Santa's elves with your ears sticking out the side, follow these steps.

1. Secure your hair in a ponytail at the crown of your head (the highest point of your skull). 

2. Place the hat on your head.

3. Close the back strap of the hat beneath the pony or pull your ponytail through the opening (watch out for velcro snags!).

4. Tuck the tips of your ears slightly under the sides of the hat so they aren’t sticking out.

5. Optional Step Pull a tiny bit of hair over your ear tips (You only need a little bit; otherwise, this may exaggerate your ears, which is what we are trying to avoid).

6. Optional Step Pull two strands out at the front to frame your face (make sure these strands are not coming out from the bill but from the sides of the brim so it actually frames your face, not covers it).

7. Don’t be shy… mess up the ponytail part a bit! This will add some volume!

The Tight Bun

When learning how to wear a hat with long hair, this is definitely a go-to style. It’s easy and fashionable. This style is perfect for when you want a neat, polished look that keeps your hair completely out of the way. It's especially great for those days when you're working out or just want a sleek, no-fuss vibe. 

1. Brush your hair back smoothly and gather it into a tight ponytail. Place the ponytail at the crown of your head (you don’t want it to be squished by the hat, so making sure it’s in the right spot is key). 

2. Twist your ponytail tightly, then coil it around the base of the ponytail to form a neat bun.

3. Use a second hair tie to secure the bun firmly in place. (You can add a few bobby pins around the base if you have thicker hair and want to ensure it stays put).

4. Place the hat on your head, making sure the back opening sits right above your bun.

5. Use your fingers to gently guide your hairline and any stray hairs under the hat (you can use a little hairspray or gel to tame any flyaways).

6. Adjust the hat's back strap to your liking, ensuring it's not too tight but feels secure. You should be able to wear it comfortably without the hat wobbling or feeling like it's crushing your bun.

The Half-Up Half-Down

This is a super cute and popular hairstyle! It’s a great way to keep some hair down while still having it styled and out of your face.

1. Start by brushing your hair and gathering the top half into a high ponytail, positioning it where you want the hat’s opening to sit. Secure it with a hair tie.

2. Put your hat on, pulling the top part of your hair through the opening in the back.

3. Gently pull two strands of hair from the front and sides to frame your face.

4. Leave the bottom half of your hair down to flow naturally. You can add some soft waves with a curling iron or some texturizing spray to give it a laid-back feel.

The Perfect Dad Hat For Your Needs | PFH 

Typically, depending on your hair texture, you might have to stray from some styles more than others. However, the awesome thing about dad hats is that they can help facilitate these hairstyles a little more easily. 

For those of us with less texture and straighter hair, it’s harder to keep high ponytails and make volumizing buns, but with a dad hat, the ponytail or bun can easily sit in the back opening above the strap.

For those of you who have a lot of texture and volume, having loose braids might be more difficult, but with a dad hat keeping the roots of your hair in place, it’s easier for your braids to remain intact. 

When learning how to wear a hat with long hair, remember that there is only one thing to remember:

There are no rules.

Practice and play with the different styles to determine which is best for you.

Each new style should bring about a new sense of confidence. Pilates For Hotties has the perfect dad hat for you. Its sleek design is made to keep your hair in place while retaining its fashionable vibes, whether you are going for a run, practicing reformer pilates, or just going out to brunch with the girls. This is the hat for you!