Starting to Dress Like a Man (for FTMs)

Long time no see, Strangers! Where have I been? Well, I ran out of girl stuff to write about so I decided to transition to male.

Just kidding, I’m transitioning for different reasons. Because I literally am male. Surprise! I know, I didn’t believe it either.

But that doesn’t mean I still don’t love fashion. And this new adventure in wardrobe has been a new challenge. More-so because information on creating a men’s wardrobe from the ground up as an adult with a feminine body shape is just not something normally covered by men’s fashion videos and blogs. I literally emailed Real Men Real Style for tips and received NO response at all. Guess I’m on my own then. But that doesn’t mean you have to be. Just call me your fairy godfather.

Let me get this first bit out of the way. Don’t dress in nothing but oversized hoodies and jerseys because you don’t know what you’re doing and you’re trying to hide your shape. It’s not attractive and you’re more likely to look like a lesbian, which you are not, if you’re reading this. Probably. Or you can ignore me. But it’s doing you no favors. You just look sloppy. As intimidating as it can be as a first timer, immerse yourself in men’s fashion information in general. I know how overwhelming it can be because as you may know, I grew up reading Esquire instead of Cosmo and it’s still a lot to take in. But don’t worry yourself too much about fussy details. Just look around. See what you like. See what kind of man you want to look like. Experiment.

This brings me to my first big Do. Start cheap. Because you’re still experimenting, there’s likely to be a lot of stuff you try and decide isn’t for you. You don’t want to spend a lot of money in this stage. My first big round of shopping happened at Value Village. Now, this meant it was not only cheap, but for casual-wear I still actually really love pretty much everything I got. If I didn’t, I wouldn’t be out a lot of money. And if I change my mind about any of it I can just donate it right back.

Speaking of cheap, another amazing place to go is online, mainly Aliexpress and Wish. Because not only are these places affordable but they’re Asian. Why does this matter? Because you’re probably relatively small for a dude, and Asian clothes run smaller. This means you don’t have to shop in the boys section. I mean you can, but it’s probably going to be a lot of dinosaur tshirts and we’re trying to dress like men here, right? Right.

Now it’s generally assumed that clothing from sites like this are crap. That’s not necessarily wrong – they definitely can be. The key here is to read reviews, especially ones with customer photos. Lots of reviews. Check size charts over and over. Check return policies. Besides, if there’s one thing I’ve learned throughout all of this it’s that men’s clothes are of much better quality than women’s. A lot better. So you’ll probably be pleasantly surprised. And you know what? I’ve only very rarely bought something that didn’t work out. My new wardrobe is amazing.

Now, pants are the devil for us, aren’t they? Goddamn hips IjusthatethemsomuchI’mgoingtositinthisdressingroomandcryfortherestoftheday. Or nah. Because what works is going up one size and/or getting something with stretch. I’m not talking about leggings or sweats or other generally fugly things. I mean real nice dress pants and slim fit jeans. They can have stretch. And it’s wonderful. I fucking love my new $12 pants.

Another thing that’s going to show off your hips is tucking in your shirt. But I mean, don’t you have to? If you’re wearing business or formal-wear that is. If you don’t it looks sloppy. True. BUT the best hack for this is a vest/waistcoat. It covers your middle, makes you look nice and trim, disguises your hips, disguises your chest/binder, and looks dapper AF. It can also be worn as a cheaper alternative to a jacket, because getting a really nice one that fits well is hard. And you’ll end up looking better than your boss. Hell yes my dudes. Get a few of them to go with any shirt/pants combo. Get a few ties too. Ties are nice. If your tie is too long, you can tuck the excess into your shirt, and the vest will cover that up too!

Hell yes


If you wear lifts, consider ordering your shoes a size up to make room for them. That’s all I got to say about shoes at the moment.

Mini tip #2, accessorize higher up on your body to draw the eye up and help you look taller. Think hats, ties, and pocket squares. Suspenders for their vertical-ness over belts with their horizontal-ness. Definitely not belts in contrasting colors, that visually cut you in half and therefor make you look shorter. And monochromatic color schemes are good. Epaulets are very good. Shoulder pads… still pretty 80s.

Aaaand last thing I got for now, and I know this is repetition, is to make sure your clothes FIT. You’ve been going baggy to hide your curves but honey no. Just no. A well dressed man wears clothes that fit. It looks put-together, confident, and shows off your new muscles. niiiiiice. Those tips I gave above will help with the curves. If you take nothing else away from this article it’s that your clothes should fit.

That’s all I got for now. Maybe I’ll be back later with shaving tips or something 😛

Wardrobe Essentials

I just want to say that I don’t believe there is any such thing as “wardrobe essentials.” Aren’t you sick of hearing about these over and over? It’s always the same things. Black pants, jeans, White button down shirt, LBD, etc etc. But look, obviously we’re not all so much the same. The last time I wore a white button down was at least 6 years ago. Essential? Not so much. I only own jeans for cold and very lazy days. Some of you might not have either of those. As we all know from reading this blog, simple casual dresses are at least as easy, if not more than jeans, and that’s something I will endlessly preach until they day they invent something better. And the LBD, while nice and useful, did not enter my wardrobe for some time. I still don’t think I need one. The little RED dress, that’s where it’s at.
The point is, you don’t need other people to tell you what to buy or what to wear. You can accept help on what makes it easier and what looks very nice, but to use the word “essential” and parade it out there like you’re fashionably deficient if you don’t have these things is just stupid. You need to figure out what YOUR essentials are based on what you like and what your lifestyle is. Hell, maybe that means scrubs in your favorite color. For example, heels are a major essential for me. Anything else falls in the category of slippers, whether appropriate for outside the house or not. You may not feel even remotely this way. Fun, glamorous, versatile dresses are my biggest essential of all. But while I think you should definitely TRY these things, if they’re not for you they’re not for you. If you fight against this it’s going to accomplish just the opposite of what these people preaching “essentials” say they will. You won’t feel put together, you’ll just feel weird and uncomfortable.
How can you figure out what your essentials are? It’s as easy of thinking of your favorite things. What do you gravitate to every day, what do you love, what makes you happy? Think of this in a fairly simple way. Not “the pinstripe pants with the chain on the hip” but maybe “funky/dressy separates.” It should be stuff that really encompasses the essence of who you are while allowing for plenty of variation. Most importantly, don’t be afraid to experiment a little outside this territory either. It’s the key to really evolving your style and your image of yourself. If it feels wrong, don’t worry about it. But it just might feel very right, and then you’ve taken a step forward and discovered something new. How exciting is that? This way you let yourself be your own style guide. You’re better than being told what to do by TV and magazines. They don’t know you. You do.