Well... First off I'm a guy transitioning into a girl. And if your a hater, don't even reply. Anyways I don't plan on going to a store because I feel it'd be kinda awkward so I'm buying through amazon. Anyone have any ideas?
If it helps
1. I'm 5'5 Asian, I'm light tan
2. I'm not going to wear skirts. I'm wearing slacks
3. If possible shoes that will go with almost about anything.
if wearing flowy or wide bottomed slacks you can also get away with wearing comfortable boots so your feet don't hurt, people will only really see the toe of the shoe anyway.
what part of wearing heels hurts you feet? (pad or heel?) there's a tone of gel or foam padded shoe inserts and heel protectors you can put into heels to make them way more tolerable :) id blister like crazy without them, if its balance just try wearing them all day around the house when you're alone to practice
Sweetie, I'm happy for you, if that's what you really feel will be the best thing for you. However, if you're "transitioning" towards becoming a female, you are going to have to get used to being in heels, and eventually, skirts and dresses. I'm sure that you are trying to ease into this, but look around and see what other ladies are wearing. That's where you are going to have to take this.
For starters, stick with low 2-3" basic pumps of good quality, and try wearing pantyhose/tights to avoid blisters.
i'd like to open by saying I'm happy for you, being able to have the courage to even start the journey :) and I can't walk in heels either, and I've been female my whole life. if I want extra height in my shoes I choose wedges. much easier in my opinion, though not office appropriate.
and if the toes are the problem, try peep-toe or open-toe.
trial-and-error as far as the slacks, maybe find a well-fitting woman's powersuit?