I don't really like dresses or skirts. Maybe to go out I will wear when I'm on HRT but I really loooove leggings with shorts and skinny jeans. So I'll probably end up wearing those more.

I love my mini hem sleeveless/halter sun dresses. They're my favorite thing to wear. I do wear a lot of shorts and tank top/halters/cami's, but my dresses are my fav. I like skirts too as long as they're a short hem and flair out. It's usually warm where I live, but during the few months when it's chily a pair of leggings under my dress or skirt does the trick perfectly.

Though I rarely wear long dresses, I can do without the slip. Because of my weirdness "down there" I've never had to 'tuck' or anything like that. As long as I'm wearing panties, no one can tell I'm different down there unless they look really closely -and no one! will be doing that til after SRS!

Ally

I would wear dresses & skirts all the time if my wife would let me. I have 7 of each & I got them all at the thrift store, & paid less than $10 for all them!!   esther

Not as much as I used to. But for special occasions, definitely. And occasionally in the spring/summer.

For me skirts and dresses make me feel overdressed on a normal day :/

I definitely prefer skirts to pants.  I wear a skirt around the house, even in winter.  I do wear pants when practicality dictates. 

Not so much dresses.  I still have some developing to do in the breast department before my proportions will work for a dress.

I wear pants/shorts more than I wear makeup but still less than 10 times a year. It's all dresses and skirts for me.

Pants and shorts have just been such a pain. At first they just didn't fit my body right, now they fit much better but I still have to worry about the crotch area so I just don't wear them. One of the side benefits of my surgery is that I will wear them more.

Allie is right though, wearing a dress or skirt does make you stand out a little. I struggle with trying to not appear overdressed all the time. It is harder to get away with wearing a dress than a skirt but it can be done. Especially Sunday afternoon.  No one needs to know that I haven't been to church in almost 30 years, so where I live I can wear almost any of my dresses or skirts then and not be out of place. Funny thing is the boots that help me blend over the cooler months through the week will earn me stares Sunday. Another strange phenomenon is that white bobos with a plain skirt and blouse somehow makes me a nurse, which completely baffles me. Nice dress/skirt without being too dressy with the right flats and I am miraculously a real estate agent. I don't know why people think any of that but they consistently do. I still stand out but I try to minimize it as much as possible.

One thing that almost annoys me. Last fall I bought 2 dresses at 90% off plus my friends discount because she works there. It ended up with me paying $11 each instead of $130 something. They are sleeveless and only come to the knee but they fit perfectly so I had to buy them right? They are the same exact cut but one is black and one has a black, red and white stripe pattern. Both I wore over the winter once or twice with the right color hose, shoes and sweaters(have to be bold sometimes to find out what works)but I kept looking forward to wearing them over the summer. Summer came and the stripe one was fine, no stares or comments but the black one my boyfriend complained about right away, said that it was too flirty or too overdressed or something. Grrr! I think it looks good on me and I get all kinds of compliments. Men stare sure but everyone does and when a girl comments on how good it looks I always ask, "So you don't think it is too dressy?" They always say, no, that it is perfect. I don't know what to think. Should I not wear the black one?

Anyway, yep, I wear dresses and skirts almost exclusively. 

I hate frumpy but 1. I live in grunge  city Seattle. 2. I've always felt I was a misgendered super model. 3. I love looking at my improving female form, so I wear bodycon dresses around the house. It has been said that being my age and dressing like this is not consistent with others in my age bracket.

Where has this thread been all my life. Oh, it was from 2014! That was before I was born! I love skirts and just started to find some dresses I like. (see avatar) I hate that the people around me dress down so much. I don't want to be the only one and be conspicuous. Don't dress to stand out like a sore thumb if you want to blend in, right?  I do think the smiles from guys seem to have just the trace of drool when they see a lady in a cute dress. lol
'Dress up' Moni

I only wear skirts, mind you i live in the tropics so i can wear them all year round. [emoji16]

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YEEEESSSS to the dress , wearing one now with leggings . think I have about 10 and 5 skirts from denim through to classic

I like both but tend to prefer dresses 

I'm totally a punk/grunge kind of girl and have legs that are awesome for "those" kind of skirts. Skirts are my preference but I do own a couple of dresses, and the trip pants are not going anywhere either

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I love wearing both and favor skirts a little, especially maxi-skirts. Some of my clients have offices in warehouse environments so wearing a skirt or dress is not always practical. However when I'm going to be a client in an office building, I like to take advantage of that