When I started transitioning two years ago, I made a commitment to grow out my hair. At the time, I wasn’t sure what my hair journey would look like, but I knew I wanted longer hair as part of my transition. In the early stages, throwing on a hat was simple—there wasn’t much hair to deal with, so I could just plop a cap on my head without a second thought. But now, after two years of growth, my hair has finally reached a length where it needs to be styled, even under a hat.
That realization sent me on a mission. I started researching ways to wear ball caps, visors, and beanies without sacrificing style or comfort. I wanted to feel confident whether I was heading to the gym, running errands, or just having a casual day out. Along the way, I discovered that wearing a hat doesn’t mean I have to settle for a messy or unintentional look. With a little effort, I can make my hair work with my hat, not against it.
If you’re also navigating this new phase of styling longer hair under a hat, I want to share some quick and effortless styles—as well as a few that take a little extra time—so you can look and feel wonderful regardless of where you’re headed.
RELATED: Hats and Headbands: Stylish Solutions for Trans Women on the Go
Quick & Effortless Hairstyles for Hats
Whether it’s an early morning errand, a trip to the gym, or a casual coffee run, there are times when we’re pressed for time. When time is short, but I still want to look put together, these simple yet effective hairstyles have been my go-to solutions. Each one takes only a couple of minutes but makes a big difference in how I feel when I step out the door.
The Classic Low Ponytail
Best for: Ball caps, visors
Why I love it: It keeps hair tidy, prevents tangling, and works for any casual outing.
A low ponytail is one of the easiest and most effective styles to wear under a hat. It keeps my hair in place, reduces tangles, and has a sleek, effortless look that works well for casual settings. This style consistently works for me, whether I’m wearing a baseball cap for a walk or a visor for a workout.
How to do it:
- Brush your hair to smooth out tangles.
- Gather it at the nape of your neck and secure it with a hair tie.
- Tuck in any flyaways with a bit of styling cream.
Personal Tip: I used to think ponytails had to be perfect, but a little looseness adds softness and femininity. If I want to dress it up slightly, I wrap a small section of hair around the hair tie and pin it underneath for a polished finish.
The Casual Tuck
Best for: Beanies, slouchy hats
Why I love it: Sometimes, I just want to tuck my hair away and call it a day.
There are days when I don’t want to fuss with my hair at all—especially when wearing a cozy beanie. Instead of worrying about making my hair look perfect, I let the beanie do the work. The casual tuck is effortless, stylish, and cozy—perfect for cooler weather or laid-back days.
How to do it:
- Comb your hair and put your beanie on.
- Let your hair naturally tuck into the hat.
- If needed, use a little dry shampoo for volume.
Personal Tip: I like to pull out a few strands near my face to soften the look. If I have time, I add a few loose waves before tucking my hair in to give the style some texture.
Loose Waves for a Feminine Touch
Best for: Ball caps, visors
Why I love it: It makes me feel effortlessly put together.
Even though I’m wearing a hat, I still love when my hair has some movement. Loose waves add a soft, feminine touch and make even a basic baseball cap look stylish. This look is perfect when I want to feel a little extra cute, whether I’m running errands or meeting with friends.
How to do it:
- Use a curling wand or braid damp hair overnight for heatless waves.
- Shake out the curls and apply a light hairspray.
- Position your hat so your waves cascade around your face.
Personal Tip: If my waves start to fall flat, a texturizing spray revives them instantly.
Styled & Chic Looks for Extra Polish
On days when I have a little more time and want to elevate my look, I love trying styles that add personality and elegance under my hat. These styles take a few extra minutes but are worth the effort when I want to feel extra polished.
The Side Braid
Best for: Ball caps, visors
Why I love it: It keeps my hair under control while adding a soft, feminine touch.
I love the side braid for its versatility. It’s casual enough for a relaxed day out but can also look polished if styled neatly. Plus, it works beautifully under a hat because it keeps my hair contained and prevents tangles.
How to do it:
- Part your hair to one side.
- Gather it over one shoulder and loosely braid it.
- Secure it with a hair tie and gently pull the braid apart for a fuller effect.
Personal Tip: A fishtail braid takes longer but looks gorgeous if I want extra detail.
Half-Up, Half-Down
Best for: Ball caps, beanies
Why I love it: It lets me keep hair off my face while still showing some length.
Some days, I would rather not commit to a full updo but also don’t want my hair fully down. The half-up, half-down style is the perfect balance. It keeps hair out of my face while still allowing me to show off my length.
How to do it:
- Take the top section of your hair and pull it into a small ponytail or clip.
- Let the rest flow naturally.
- Adjust your hat so the ponytail peeks out.
Personal Tip: Adding a slight wave to the bottom half gives this look extra dimension.
Hat-Friendly Haircare Tips
Wearing hats frequently has taught me that proper haircare is essential to keep my hair looking and feeling healthy. These tips have made a big difference in preventing breakage, reducing frizz, and keeping my hair fresh:
- Avoid tight styles: Styles that pull too tightly under a hat can lead to breakage.
- Use dry shampoo: A quick spritz at my roots helps absorb sweat and keeps hair fresh.
- Choose satin-lined hats: If possible, I opt for hats with a satin or silk lining to reduce friction.
- Keep hair moisturized: Hats can cause dryness, so I use a leave-in conditioner or lightweight oil.
- Switch up my part: If my hair gets flat from wearing a hat, flipping my part adds volume after removing it.
RELATED: Embracing Change: Tailored Hair Care Strategies for Transgender Individuals
The Bottom Line
Learning to style my hair under a hat has been a journey. For years, I didn’t have to think about it—I’d just throw on a hat and go. But now, having longer hair means I get to explore new styles that make me feel beautiful and confident.
Some days, I go for a quick ponytail, and other days, I take the time for a sleek braid or messy bun. There’s no right or wrong way to do it—just what feels good for me.
If you’re also figuring out how to style your hair under hats as it grows longer, know that you have so many options. Whether you’re in a rush or have extra time, you can always find a look that makes you feel fierce and authentic.
What’s your go-to hat hairstyle? I’d love to hear how you style your hair under a cap or beanie!
