This is not a post on gender-identification, and much less about sexual orientation. It is not a post on being trans or trying to pass. This a simple post on how to look good when gender-bending fashion from someone who has been doing it for years.
I generally rock a dapper look. Shirts, ties, vests you get the idea. Also, a word on my body type. I am tall and skinny with round hips and very little boobage. I would appreciate people with experience in cleavage to post their tricks, because I can’t speak from experience here.
Wear men’s shirts:
Like, literally, NOW. Men’s shirts are better constructed, better quality and there are so many more options than women’s shirts. And do you know what? Men’s shirts are loooong. They actually cover your butt and stay in your pants, unlike the annoying waist-baring cut of women’s shirts.
Try sizes and cuts to see what works. Men’s shirts kindly have all that info printed on the label! For me, that would be slim-fit. There are online shops that have gender-neutral shirts now, but I have not tried them yet. From what I gather, they are a huge help for people with boob fit issues?
Avoid excess flappy fabric that makes you look like a kid playing dress-up. There will be problem areas, for sure. Personally, I generally have too much loose fabric pooling at my lower back, where the shirt tucks into my pants. One way to minimize this is to wear either high or low waisted pants. Mid-waist seems to make it worse. Also, leave the bottom button(s) that are hidden in your pants undone. It creates a less snug fit around your hips, and you can tuck the shirt better. You can also just throw on a vest or sweater.
If you own a sewing machine, sew two darts up the back of the shirt. I promise, it’s easy. Pinch the fabric from high up, near mid-shoulder blade and create a crescent-shaped dart to where the shirt is in your pants. It’s just sewing two straight lines. You can do it, promise.
I have given up on sleeves. They are not worth altering. I just roll the cuffs. If you have a nice shirt with a cuff in a different color/pattern (cause guys shirts do that and it looks awesome!) there is a way to roll and not lose the effect. It’s called the gangster cuff, Google it.
Wearing a men’s shirt will not make you look like a man. Just like a better-dressed woman. Start with a plain white button-down. You can look absolutely femme if you pair it with a flirty skirt, leave a few buttons undone and add a necklace. And once you’ve tried it, you might get hooked. Just saying…
I love ties. They are the equivalent of statement necklaces. They add color, pattern and snazzy up an outfit. Go bold. I like to do the opposite of my shirt, pattern-wise. A patterned shirt with a solid tie or a crazy tie with a plain shirt. And I also leave my top-most shirt button undone for a more casual look. (Okay, it’s actually because I feel strangled all buttoned up.) Try a bow-tie too!
If you want to invest in proper tailoring for one item, choose a vest. A good quality vest in a classic pattern — like black or a subtle pin-stripe — that fits you well will become your most treasured possession. You can choose to have it tailored to mask or emphasize your feminine curves and waist. It will not only look amazing, but it will also help hide any fit issues with shirts.
Try a hat. Or a men’s sleek belt. Or dapper-boy tooled leather shoes. Wear them with a skirt to better show them off.
Go all out dapper. Or not:
Sometimes, I purposely wear a push-up bra with my shirt and tie, just to muddle people. Not usually, but sometimes. Or pair a very feminine up-do with a strict business look. You can be as blatant as you like about gender-bending, or you can smile secretly at the feeling of subtly toying the line.
Tips on shopping:
It can be intimidating to shop in the men’s section. If you’re anxious, start online maybe. I say “maybe” because fit is hard to get right online even if you know your proper size.
Better to start in a big discount warehouse type place. You know, the one where there is no service if you need a different size and only one blasé attendant manning the cavernous changing rooms? My first time, I brought both men’s and woman’s wear to try. Even if I had no intention of trying on the dresses.
A word on dealing with judgey people:
Most people in my rural area, either assume it’s a fashion choice, or that I’m lesbian. I don’t much care what clients assume, and I am not about to embark on a rant on the difference between gender and orientation in the middle of the grocery store.
Just ease yourself into it until you are confident. The first time I wore a tie to work, after months of wearing men’s shirts and belts, I was pumped up. Bring on the comments, I was ready. There were hardly any. I think one older man said I “looked cute.”
The few degrading comments I’ve had can generally be dispatched with humor. “Is that a men’s tie?” Can easily be replied with “Well, it’s on a woman, so technically it’s a woman’s tie now.” Children can be brutal. I don’t hold it against them — I like to explain simply that I wear what I like and I like the color of this shirt and so can they if they want. If anyone persists in being a jerk, a firm “I like it,” and walking away, works well.
In conclusion, it’s just clothing
Wear what you like, what looks good on you. Don’t worry about a label, or which section it came from. You be unapologetically you.