Skirts and Dresses, any advice?

So, little back-story. I'm 17 and current;y attend college so the dress code isn't that sophisticated aside from no inappropriate clothes (revealing etc). Now here's one of the most important and i guess, deciding factors: I'm transgender (male to female).

I've never worn a skirt or dress aside from tying them on in stores, my parents aren't that accepting so if I was to buy one, I'm not sure what the reaction would be (it probably wouldn't be a nice "oh that's nice hunny" etc)

My main questions are:
What are the best shoes to wear with skirts/dresses? (I mainly only wear trainers/sneakers, this probably wouldn't work or look good. I'm thinking simple pump-style shoes?)

How would I get over the self conscious aspect of the skirt/dress riding up, being too "short", blowing up in the wind etc? I don't think I would mind so much, it''d just be the first few times, you know?

What's the best under wear to wear with a skirt/dress? I only own thongs, I just find them comfy, simple, and hide VPL's. I have heard of "slips" although I don't really know the purpose of these, nor have I ever seen one.

What could I style a skirt/dress with? I usually wear an over-sized jumper dress (too short to be worn as a dress alone) with leggings and my coat. I generally wear a pastel backpack with me whenever I'm at college. I was thinking maybe tights/stockings (I feel it'd be more classy, plus my legs are really pale so I feel they'd look better if I wore tights/stockings over them) a cute t-shirt and a denim jacket. Although for that I would have to buy a whole new outfit essentially, welcome to the trans life. *rolls eyes*

This is going on quite a bit, basically any information for a girl's first time wearing a skirt, what to expect, what to wear it with etc etc. Thank you!!

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What Girls Said 2

  • I like flats, converse, sandals, ankle booties, and wedges with dresses
    Wear some shorts underneath
    Thongs or boy shorts for me
    Tights, cardigan, and wedges.

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  • It depends on your sense of style. There isn't a set recipe.

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