Q&A for How to Wear High Heels (for Men)

Unless there's a dress code, no. You can wear whatever you're comfortable and happy in. That's what's so great about fashion; it's all about expressing yourself as you see fit! If you don't like heels, don't wear heels, and don't let anybody tell you otherwise.

Go for it! You already have the basics down, so it's just a matter of getting used to that extra inch of height and a slightly higher angle of the foot. Take slow, small steps at first and keep your legs relaxed. Practice on flat ground before you move on to bumpy sidewalks, stairs, or hills.

For short men, high heels are really good for giving the illusion of being tall.

This is a tough situation, so the best thing you can do is remain calm if your parents see you dressed in female clothes. Gauge their reaction. Do they seem angry, or simply shocked? If they're surprised and maybe a bit upset but not mad, leave the room and give them time to calm down. Change your clothes and wait for them to approach you. If it's been more than a couple hours, go find them yourself and talk. Be gentle with them, as it's natural for them to be surprised. If they seem willing to understand, be as honest as you feel comfortable with. They may eventually open up to it and accept you for who you are. On the other hand, you should understand that your parents may react with anger. If this is the case, leave the room immediately. Go to your room or a trusted friend's house. Wait until you feel your parents have calmed down to return. Be honest with them if you can, but if it seems like they're in denial or may still get angry, don't open up completely. Say, "I think we both wish you hadn't seen that. We can talk about this or not, and I understand that I'm living under your house and your rules." You may be forced to throw away any female clothes or shoes you have. This is not the right way for your parents to react, but it is their right to set the rules in your house. Remember that they're trying to do what they think is best for you. It may hurt or feel difficult now, but eventually you'll be able to leave home and live your life any way you want to.

There are no rules, just wear what you are comfortable with. I'm sure a lot of guys go straight to three or four inch heels.

Try a 10 wide if you can find it, or a 10.5. Women's shoes are sized differently from men's and tend to be a bit more narrow, so if you can't find half sizes, either go to another store/vendor that may have them and find another style you like, or try to find your style in a wide variant.

It will generally be easier to wear whichever high heels that fit your foot. If the shoes are too big, you will get blisters and hot spots(precursors to blisters). If the shoes are too small, your feet will be crushed and it will hurt to walk. Typically, if they are the same model and whatnot, the steepness will all be about the same. Make sure you find out what shoe size is a snug fit for you before doing the math for women's shoe sizes. Also, if you aren't sure if they will fit you and you are trying them at home, wear nylons. It'll make them easier to put on and it will keep the shoes clean. It's kinda a girl code type of thing. Always wear socks when trying on shoes.

It’s understandable that you’d be worried about how others would feel about this. If you want to wear female clothing, and you have a female friend you can trust, you could borrow from her. Otherwise, you may want to start small, by buying something such as jeans or a shirt from the women’s section, something that would not incite suspicion. If anyone asks, you could say you really liked the shirt and didn’t see a similar one in the men’s section, or that women’s sweatpants are more comfortable. If you have a credit card, you might also be able to buy clothes secondhand off the internet, although you should be careful about which sites you buy from.

You cannot control what other people do. Be yourself, but be prepared that others may not agree with your decisions.