CROSSDRESSING NEWBIES: WHAT I WISH SOMEONE HAD TOLD ME

When you first start crossdressing, it can feel like you’ve stepped into a world with no map. It’s exciting, scary, confusing and comforting all at once. 

I remember the feeling clearly. The push and pull of wanting to explore while also wondering what it meant, whether I was “allowed” to enjoy it and whether anyone else would ever understand. 

Those early days were full of questions I didn’t yet have answers for.

That’s why I wanted to write this guide. I’m not trying to provide any rules. It’s simply the things I wish someone had whispered in my ear when I was a crossdressing newbie, figuring things out one tiny step at a time. I hope it helps you.

YOU’RE NOT WEIRD, BROKEN OR ALONE

I want to begin here because this is the feeling so many people carry quietly when they start exploring. You are not strange, bad or doing something wrong by wanting to wear clothes that are traditionally associated with another gender. 

Crossdressing is far more common than people think, and people of all genders, ages and identities do it for many different reasons. Curiosity, comfort, expression, joy, sensuality or simply because certain clothes feel more like “you” than the ones you’re expected to wear. 

What you’re feeling is human. 

You’re exploring yourself and there is nothing shameful about that.

YOU DON’T HAVE TO LOOK PERFECT TO DESERVE THIS

One of the biggest pressures crossdressing newbies often feel is the idea that you have to look flawlessly feminine or convincingly masculine in a way that society won’t question. That pressure is exhausting and unrealistic. 

You don’t need perfect makeup, the “right” body shape or the exact outfit you’ve seen online to enjoy dressing differently. Crossdressing doesn’t have to be a performance or a transformation. 

It can be as simple as choosing a top that feels right or slipping into soft lingerie that helps you breathe a little easier. 

You deserve to feel good in your clothes long before you “perfect” anything.

YOU DON’T HAVE TO GO ALL IN

You might imagine crossdressing as something big and dramatic, but it doesn’t start that way for most people. 

You can begin with one or two pieces. A simple bralette, a piece of jewellery, a pair of tucking briefs, a robe you wear at home. Underdressing is a particularly gentle way to begin. Wearing something that feels like yours, even if nobody else sees it, can be incredibly grounding. It doesn’t have to be “all or nothing.” Quiet beginnings are just as meaningful as bold ones.

SIZING IS ODD: IT’S THE CLOTHES, NOT YOU

This is something I wish someone had explicitly told me: women’s sizing makes no sense. One brand’s medium is another brand’s XXL. Lingerie sizing is its own universe. None of this has anything to do with your body or whether you “look right.” 

You are not defined by a number on a label. Try things on when you have the time and space. Expect a little trial and error. Focus far more on how a piece feels than what size it claims to be. And be kind to yourself in the process. Your body isn’t wrong. The sizing system is.

COMFORT MATTERS MORE

If you Google crossdressing lingerie, you’ll often be shown things that are very intense. Lots of lace, stockings, push-up bras, frilly nightwear. 

It’s beautiful if you enjoy it, but it’s not where most newbies feel comfortable starting. There’s absolutely nothing wrong with choosing simpler or more androgynous lingerie to begin with. Soft bralettes, tucking briefs or feminine but minimal layers are all gentle entry points. 

And if you’re AMAB, please don’t underestimate the power of tucking underwear. The right base layer can make your first outfits feel safe, comfortable and natural. You don’t have to jump straight into lingerie that feels overwhelming. Ease yourself in.

IT’S OKAY TO KEEP THIS PRIVATE (FOR NOW OR FOREVER)

Feeling afraid of being seen is normal. 

Worried someone might find your clothes? Totally normal. 

Thinking you’ll only ever crossdress in private? Also normal. 

You don’t owe anyone your crossdressing. Doing it privately doesn’t make it less real, less valid or less powerful. You’re allowed to have rituals just for you. Getting dressed up at home, wearing a robe while you read, watching TV in clothes you only wear when the door is closed. Privacy can be a soft and safe place, not a limitation.

YOUR FEELINGS MIGHT SURPRISE YOU

Crossdressing can stir up all sorts of emotions. You might feel joy one moment, then guilt or confusion the next. You might feel gender euphoria or you might wonder what these feelings “mean.” 

This is all normal. 

Clothes are loaded with meaning and exploring them can touch very tender parts of our identity. Try not to panic. Let yourself feel whatever you feel. If it helps, journalling or talking to someone supportive can soften the confusion. You’re not broken for having emotions about this. You’re human.

YOU’RE ALLOWED TO CHANGE YOUR MIND

Crossdressing doesn’t lock you into anything. You don’t have to decide right away whether this makes you trans, gender-fluid, a crossdresser or simply someone who enjoys certain clothes. 

You’re allowed to expand, retreat, change direction and experiment. Some people crossdress occasionally for comfort. Others find it opens doors to deeper self-understanding. There’s no contract to sign here. Your style and expression can evolve as you do.

YOU DESERVE TO FEEL GOOD IN WHAT YOU WEAR

Try things on when you have time, not in a panic. Move around in the outfit. Sit, walk, stretch. And feel how your body responds. Have one outfit that feels safe and easy for days when everything feels overwhelming. Build slowly rather than buying everything at once. And remember: the goal isn’t to create a perfect look. It’s to feel comfortable and connected to yourself.

Above anything else, I wish someone had told me this sooner. You deserve softness. You deserve comfort. You deserve to feel good in your clothes. Not someday, not when you “look better,” not when you’ve figured everything out. You deserve that now. Crossdressing can be a powerful way to connect with yourself, an act of self-care rather than something to feel ashamed of. You’re allowed to enjoy it.

SUPPORT FOR YOUR FIRST STEPS

At Gaff and Go, everything we create comes from lived experience. Our range is built for trans and gender-diverse people who want to explore clothes in a way that feels gentle, affirming and safe – especially when you’re just starting out. 

From bras and bralettes to tucking lingerie and sports briefs and trans sports bras, each piece is designed to support your body rather than fight against it.

If you’re curious about playing with shape, you can also explore options like breast pads, breast forms or packing underwear when the time feels right, alongside trans lingerie robes and party pieces for when you’re ready to feel a little braver. 

If you’d like some simple, comfortable starting points as you explore this part of yourself, you’re welcome to browse the Gaff and Go collection and see what feels right for you.