A Beginner’s Guide To Embracing Trans-Masculine Style

It is a common cliche to say confidence is what makes you look sexy, but it’s true.

Style is personal, so let me tell you what to do. Just kidding! But I do know how overwhelming it can be as a masculine presenting person when you’re trying to look good in a way that isn’t often displayed in traditional media. Sure, we might have style inspirations like Finley from The L Word: Generation Q (I’ll count anyone who wears button downs, by necessity), but sometimes those of us who aren’t yet camera ready could use a little helpful advice.

Hi, I’m Nik. I used to be like you: unfashionable, overwhelmed, and without a clue on how to dress. In many ways, I still am that person. My fashion is evolving every day. I grew up as a “tomboy” (whatever that means) and didn’t come out as a trans man until I was about 22. In that time, I tried a lot of different ways to appear more masculine. Some worked. Others screamed, “Over compensating!” The only thing that really made me feel confident in my masculinity was staying true to myself and learning to love the body I have (read: I went on testosterone and it literally solved 80% of my problems).


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While testosterone is awesome, it’s not for everyone. Another important piece of feeling confident in your looks is style. So I have gathered a list of style tips that helped me get more confident in how I present myself to the world. I had to try and fail and try some more until I realized what actually looked good on me — and what just made me look like I was trying way too hard.

Take all of this advice through the lens of your own experience. You know your body and your preferences better than anyone on the internet. Style is meant to be fun, not a burden. If, at any time, these tips become overwhelming, I give you permission to wear a groutfit (grey sweatpants and a gray sweatshirt) for the rest of your life. Without further ado, my trans masculine lovelies, here are 10 tips for how to make your style work with you, not against you!

Do loosen up your buttons, babe.


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This bit of fashion advice comes from a personal experience. A few years ago, I tried buttoning my shirts all the way and multiple people told me, “Men don’t do that.” While I think men are much more experimental with their fashion choices now, people of an older generation might see the full button-up as feminine. Also, if you are binding or pre top surgery, or don’t want to draw attention to your chest, I would stay away from buttoning your shirt all the way up as it can exaggerate the area.

Do layer your shirts.


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Layers afford the opportunity for a visual contrast. Wearing a t-shirt under a button-up, say, with the buttons undone can draw your eye to the outer layer. Having a tight undershirt under your t-shirt can help give a streamlined look. Putting a hoody on over a tight t will also be helpful — just make sure it’s not too baggy. Speaking of baggy ….

Don’t wear huge baggy clothes that you’ll trip over.

This might seem like a contradictory tip, because you would think baggy clothing would hide curves, but pay attention. I am especially referring to pants. Every body is different. I personally would love to hide my proportions, but I’ve noticed that when I settle on baggy pants, I end up looking ridiculous because my butt is simply too big. Pants that are baggy on my backside make my legs look as if they belong on an elephant. Now that I have accepted that my butt will fill in my pants, I wear pants with a more natural cuff that sits on my boots or sneakers. For those looking for more room, athletic-fit jeans are a great option because they offer some give in the seat while tapering at the leg, without strangling you like skinny jeans.

Do wear looser-fitting clothes. You don’t want them to be skin-tight.

That being said, skin-tight clothes will hug every curve and give you nowhere to hide. A hoodie is a good option in the cooler months because you can skip the binder and give yourself a break.

Don’t listen to the haters.

Everyone has an opinion about fashion, but that doesn’t mean everyone knows more than you. There is conflicting advice all over the place. Can you wear stripes? Can you not wear stripes? Are binders dangerous? (They can be!) Do I go a size up or a size down? At the end of the day, worry about the things YOU will see in the mirror. Take some time in the morning working on your look so you don’t accidentally ruin your whole mood if there’s a reflection out in real life, but don’t spend an hour picking yourself apart, either.

Do read advice from GO Mag.

Some advice is simply better than others. What can I say? I wouldn’t give any advice that I wouldn’t take myself. Although I am currently wearing a groutfit, my sweatpants are fitted joggers. You don’t have to give up looking cute even if you want to be comfortable!

Don’t wear light-colored shorts if you are self conscious about your large butt.


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If you’re like me, and can’t get through a style tip article without mentioning your butt at least twice, this one’s for you. Light-colored shorts and pants will make your ass look bigger. I’m not saying it’s off limits, wrong, or bad. If you want to draw attention to your booty, more power to you. I am self conscious about my butt so when I’m going to have pictures taken from behind– say I’m going bowling– I will wear dark jeans or shorts. If I’m going to a Pride event, or the beach, I will wear light shorts and let the comments flow in, empowering me, making my butt grow and absorb queer strength and mass.

Do wear shorts that end above your knees.

There are only two people who should wear Adam Sandler shorts: Adam Sandler and Karyn from The Circle. You will not convince anyone of your masculinity by hiding your gorgeous thighs. Your knees need to see the sun and besides, it’s inhumane to hide them. Even professional basketball players wear cute shorts off the court. I would get a subscription box to Chubby’s if they made them.

Don’t cut off all your hair because you think any short hair is masculine. You might just end up looking like Natalie Portman in “V For Vendetta.”

Haircuts can be intimidating. The most magical moment can come when you decide to take your hair from butt crack accessory to pomade worthy. But! All short hair is not equal. If you think the shorter the better in terms of looking masculine, I have news for you: your haircut needs to have certain angles to look more masculine, if that’s what you’re going for. Don’t let the stylist or barber keep it “fluffy” in the back, which will give you more of a pixie cut look. Ask them to square it off for a thicker-looking neck. Leave some length on the top so you can do what you want with pomade. And, for God’s sake, enjoy your thick, full head of hair while you can if you intend to go on T.

Do remember that nobody is thinking about what you look like as much as you are. So have fun with your style and carry yourself with confidence.

It’s a common clichè to say confidence is what makes you look sexy, but it’s true. Nobody is going to pick your outfit apart more than you are. The most important piece of advice? Be confident in yourself and your style. If you’re constantly picking at your wedgie or trying to pull down your shirt to hide your stomach, it will look worse than actually having a wedgie or a stomach. And you can’t please everyone; just please your fabulous self (and trust me about the buttons).

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