As the cool winds of fall start to blow, many of us are reaching for our favorite headwear—beanies, berets, and other cozy hats that keep us warm and stylish. For transgender women, especially those who are in the early stages of their transition, fall fashion can be both an exciting and challenging time. Hairstyles are an integral part of how we express ourselves, but how do you showcase your unique style when it’s tucked under a hat?
I’m a 55-year-old transgender woman, and I understand deeply the complex emotions tied to hair during transition. My own journey with hair has only just begun. I’m watching it grow out, little by little, and I’ve learned that hair isn’t just about aesthetics—it’s about identity, freedom, and authenticity. I know firsthand the pressure that can come from society’s rigid ideas of how women should look. But let me tell you this: your hair doesn’t define your womanhood, and you deserve to express yourself in ways that make you feel good.
For many of us in the transgender community, especially in the early stages of transitioning, hair can be a sensitive topic. Whether you’re in the process of growing out your hair, have recently started HRT (hormone replacement therapy), or are sporting a short crop, the way you style your hair—and how it makes you feel—can be transformative. As we head into hat season, I want to share some easy-to-follow tutorials that will not only help you stay warm but also look fabulous, no matter where you are on your hair journey.
This guide is designed to celebrate you and your unique path. Let’s dive into some beautiful, empowering hairstyles that will have you turning heads, even under your favorite fall headwear.
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Embracing Soft Waves Under a Slouchy Beanie
If your hair is just beginning to grow out, one of the easiest ways to give it body and texture is by embracing soft waves. Soft waves add movement and femininity to your look, and they pair beautifully with slouchy beanies. These hats are forgiving in size, allowing a bit of room for hair to peek out naturally, framing your face in a flattering way.
How to Achieve Soft Waves:
- Step 1: Start with damp, towel-dried hair. If your hair is shorter, use a lightweight mousse to add volume and hold.
- Step 2: Divide your hair into small sections, then braid each section. If your hair is still on the shorter side, two or three braids will work; if your hair is longer, you can go for four or more.
- Step 3: Let your hair air dry or speed things up with a blow dryer set on low heat. Once dry, unravel the braids and gently finger-comb your hair to loosen the waves.
- Step 4: Slip on your slouchy beanie, letting some of the waves fall around your face for an effortlessly chic look.
Why it Works: Soft waves under a beanie add an extra layer of softness and femininity, which can be affirming if you’re early in your transition. It’s an easy, low-maintenance style that works even with shorter hair lengths. The best part? It’s comfortable and works perfectly with the laid-back vibes of a beanie.
Elegant Side-Swept Locks for a Classic Beret Look
A beret can be a wonderfully feminine and sophisticated addition to your wardrobe, and it pairs beautifully with side-swept locks. Whether your hair is chin-length or longer, sweeping it to one side can create a romantic and classic silhouette under your beret. This look works especially well for those who have already grown their hair out a bit but is adaptable for shorter hair with the help of styling products.
How to Achieve the Side-Swept Look:
- Step 1: Start by parting your hair deeply to one side. If your hair is still short, use a volumizing spray at the roots to give your hair some extra lift.
- Step 2: Use a curling wand or flat iron to create loose curls, starting at the mid-shaft of your hair. The goal is to give your hair movement without it looking too “done.”
- Step 3: Sweep the curls over to one side, securing them in place with a few bobby pins at the nape of your neck if needed.
- Step 4: Top it off with your beret, angling it slightly to the opposite side of your hair sweep. This creates a balanced, chic look that’s perfect for an autumn day out.
Why it Works: The side-swept style is a great option for a more polished, elegant vibe. For many transgender women, this look can feel affirming because it’s so classically feminine. A beret sits lightly on your head, allowing your styled hair to remain the focal point.
Playful Pixie with a Fitted Hat
If you’re rocking a pixie cut or are still in the early stages of growing your hair, you may think there aren’t many options for styling your hair under a hat. But short hair can actually be incredibly versatile and playful. A fitted cap, like a snug beanie or newsboy cap, can emphasize the edginess of a pixie cut while keeping things playful.
How to Style a Pixie with a Fitted Hat:
- Step 1: Start by applying a texturizing spray or pomade to damp hair. This will help give your pixie definition and texture.
- Step 2: Use your fingers or a small brush to tousle your hair, pushing the front up for some added volume or slicking it to one side for a sleeker look.
- Step 3: Slip on your fitted hat, making sure your hair at the front and sides is still visible. You can leave a few pieces out for a more relaxed, carefree vibe, or tuck everything neatly for a sharper, more polished appearance.
Why it Works: Pixie cuts are bold and empowering, and pairing them with a fitted hat can highlight that sense of confidence. This style is perfect for colder days when you want to keep things simple but still chic. It’s a low-maintenance look that can feel especially freeing for those still in the early stages of hair growth.
Low Bun with a Cozy Knit Hat
If your hair has grown out long enough to gather into a bun, a low bun paired with a cozy knit hat can give you an effortlessly cool look while keeping you warm. This style works well with medium to long hair and can be a great way to show off your hair’s length without having it get tangled under your hat.
How to Create the Low Bun Look:
- Step 1: Start by pulling your hair back into a low ponytail at the nape of your neck. If your hair is on the shorter side, you can create a half-bun using only the top section of your hair.
- Step 2: Twist the ponytail into a loose bun and secure it with bobby pins or a hair tie.
- Step 3: Pull on your knit hat, allowing the bun to sit comfortably at the nape of your neck. For a softer look, you can leave a few face-framing strands out.
Why it Works: The low bun is timeless and sophisticated, while still being casual enough for everyday wear. This style can be especially affirming for those who are growing out their hair, as it highlights your length in a subtle and graceful way.
Tucking Away for a Sleek, Clean Look
Sometimes, simplicity is key. If you’re in a rush or just want a clean, minimalist look, tucking all your hair under your hat can give you a sleek, streamlined appearance. This works for any hair length and is a great option if you’re having a “bad hair day” or just want to focus on your outfit rather than your hair.
How to Achieve the Tucked Look:
- Step 1: Start by brushing your hair back so it lies flat against your head.
- Step 2: Apply a bit of smoothing serum or gel to keep everything in place.
- Step 3: Put on your hat, making sure to tuck any loose strands underneath for a clean, polished look.
Why it Works: Sometimes the best way to feel confident is to simplify. This style is perfect for those days when you just want to focus on comfort while still looking put-together. It’s a reminder that your womanhood isn’t defined by how much or how little hair you show—it’s all about how you feel inside.
Navigating the Emotional Journey of Hair During Transition
Now that we’ve covered some fabulous styles for hat season, let’s talk about the emotional side of styling hair as a transgender woman. I understand how difficult it can be to feel confident when society bombards us with narrow ideas of femininity. If you’re early in your transition, you may feel frustrated by how long it takes for your hair to grow or anxious about how others perceive you. Those feelings are valid, but it’s important to remember that femininity comes in many forms.
Whether your hair is long, short, wavy, or straight, your beauty is real and valid. Hats can be a wonderful tool for self-expression during the cooler months, offering a chance to experiment with different styles while staying warm and comfortable. As you navigate your journey with hair and fashion, allow yourself the space to experiment and, more importantly, to embrace who you are at every stage of the process.
The Bottom Line
As the temperature drops, remember that fall fashion is about more than just staying warm—it’s about expressing yourself and feeling good
in your skin. Your hair is an important part of that expression, but it’s only one piece of the puzzle. By experimenting with different hairstyles under beanies, berets, and other fall hats, you can find new ways to showcase your evolving identity.
As a transgender woman, you’ve likely already faced many challenges, and finding your style is just one more opportunity for self-discovery. No matter where you are in your journey, know that you deserve to feel beautiful, confident, and comfortable in your own skin.
So as you step into this fall season, embrace the warmth, the layers, and the hats that keep you cozy. Most importantly, embrace yourself. You are beautiful exactly as you are, and your style is a reflection of that truth.
