Men in Heels?

A primer on How to Wear High Heels (for Men):

Go with stilettos if you’re feeling confident and experienced. Stilettos have the classic thin, high, tapered heels. They’re gorgeous, but notoriously difficult to walk in! If you’ve walked in lower heels before and feel up to the challenge, buy a pair and try them out.

Don't give up if you can’t manage the height. Keep practicing, and you’ll be rocking them in no time.

Practice your walk in front of a mirror a few times. Keep an eye out for a few common mistakes of walking in heels, such as letting your ankles wobble from side to side or keeping your knees stiff, which will cause you to lean forward and have bad posture. You might also see that you’re leaning back too far as you walk, which means that you’re keeping your thighs too tense.

Remember to stand straight with your shoulders back and stay relaxed through your hips and knees.
Alternatively, film yourself walking, then watch the recording. Note any mistakes, such as wobbly ankles or stiff knees.

Walk on the streets if you’re feeling comfortable and confident. When you’re ready, wear your heels in more normal streets and busier areas. Keep an eye out for any bumps, cracks or grates in the sidewalk. If you’re still feeling shy or nervous, remember that most people won’t even look at you long enough to notice your shoes. Act normally and walk confidently; by now you’ll be a pro at walking in heels!

If you get harassed by someone, ignore it and keep walking. If they see that their words don’t stop you from rocking your heels, they’ll probably give up.
If they keep pursuing you, duck into a crowded store or turn a corner. If all else fails, call the police.
No matter what happens or what anyone says, don’t let bullies or a bad experience ruin your confidence.