I've no idea what kind of clothes I'd feel comfortable wearing

How does your wardrobe closet look? Is it spacious? Full of clothes? Is it easy to take out the clothes and put them back? Do you have a hook on the door where you can hang the outfit you are about to wear?

Maybe start there. If clothes can make your day, give them the attention and care they deserve. If you don't have a place of a bigger closet, what about a clothes rod? Buy new hangers if you need them, so that every piece of clothes has its own. Declutter your closets.
The less clothes there will be and the more space to look at them the easier the decision making will be.

Underwear can be a great way how to boost up your confidence too Even though no one is going to see it, YOU know what you are wearing under the clothes.

 

When I first started questioning, I had such a hard time with clothes. I'd start my day dressed as one gender (usually female) and flip to the next at the drop of a hat. And god would I get sullen if I couldn't change. The whole thing was, unquestionably, horribly inconvenient.

I do still have some women's clothes, though they're in the minority of my wardrobe now. I've weeded out most of the things that make me uncomfortable.

I suspect, given the manner of your writing, that your reasons for being so uncomfortable with your clothes don't stem from the same place mine do. But if you're looking for people that understand, I do. I've had a similarly rough experience.

It might be best to just take a day and do a closet overhaul. Pull everything out and sift through it. Try things on and check the fit in the mirror. Keep whatever makes you feel good about yourself, and send the rest off to a thrift shop. Then, look for trends in the things you're keeping, and base your shopping around them in the future. It's tedious for sure, but it'll probably help if clothes can make an impact on your day easily.

 

Two words: Try everything. Clothes are something of a specialty of mine.

When I identified as female, I would try on everything in a store, pretty much literally. Just try on everything. Experiment with different colors, textures, patterns, and silhouettes. Maybe try on stuff that's a little out of you comfort zone and then notice how it makes you feel, both on you and when you look in the mirror. Thrift shops are great places to go for this because you can try on and buy lots of stuff and not spend a whole lot of money. It's a long process of trial and error, but it's very worth it.

 

Unfortunately you can't control who is attracted to you. But if a guy tries chatting you up just say quite clearly '' I'm not interested, sorry''...that certainly appears confident! Haha. Now as to your general insecurity I can totally relate! I was bullied all through high school by boys about my looks. I was so insecure up until a year or so ago. I don't know what happened. I just kept thinking to myself that I didn't care what other people think. And then it sort of happened. The ways in which I improved my confidence where by trying new things. Putting myself in situations that made me uncomfortable and dealing with them. For example I'm a bit of an introvert, so I started the converations when I met new people, and after a while it made me more confident. Also, hold your head up when you walk etc. This all improved my confidence.

But the number one thing that really increases confidence is being happy. When I'm down no matter what I try I feel rubbish. So try and do things that make you happy and you enjoy, and be around people that make you happy! Hopefully this will really help with the confidence issues

 

As an earlier reply said, give your daily outfit a little attention. Look at yourself in the mirror, then go by your instinct, do you feel comfortable?

I hear extremes in your descriptions, you talk of tight clothes and baggy clothes, when I think that something in-between is probably your thing - not skin tight, not baggy, but well fitting with a little bit of room to flow. I find that buying quality clothing helps, and knowing which shops sell the clothes for a person of your height and shape - some shops specialise in short women, others in medium, and others in tall. Quality clothing that keeps it shape well, may cost a bit more, but there is so much value in it, and it will last longer than cheaper stuff, and you will always look tidy.

I get the impression that you would like to see yourself looking more feminine, but don't want the attention that goes with. Yet the flower attracts the bee, and looking good will always attract admirers. I hope you find a way to deal with unwanted advances well. And not worrying about what other people think is a difficult one; perhaps just realising that you don't know what others are thinking, is a good thought to hold in mind; when feeling self conscious a person is only assuming that other people are thinking about them in a negative way; accept that you don't know what others think, smile and be friendly, and you will always get the best out of any situation.

 

@evora Maybe you can also have days on wich you like to dress girly and days on wich you don't at least thats what I have now. During puberty and a bit after that I liked to dress male as I was mainly attracted to women then and did not want attention from men. But now I even where skirts sometimes, I can be totaly fine with it for days on end and then be totaly fed up with it, change clothes, and feel confident again.

You also do remind me a bit of my very pretty niece who has had, or maybe still has a mild eating disorder, see always thinks she's ugly and fat, but she's very pretty in the eyes of many, thats propably why she gets quite a lot of attention from guys, wich makes her shy.

Best,

Marieke

 

I'm kinda in the same situation as you. I hate the clothes I wear, I'd prefer to wear male clothes rather than female ones. But it's extremely difficult to find what you like