I usually wear dresses, mostly because I have serious sensory issues and many types of pants (such as jeans) send me into sensory overload.
Be aware, there are pretty big cultural things all women have to deal with when we wear dresses that trans women who are new to wearing dresses may not be fully aware of, yet. Yes dresses are lovely, but people are often down to police women's clothing, and dresses are an huge example of it. As a cis woman I have been navigating the pushback of wearing dresses and skirts daily, for nearly 40 years. Here are comments I have gotten, as a woman wearing dresses.
"You really don't need to be so formal when you come to this job dressed like that. What are you expecting here?" - this was a job I had in a kitchen where I wore a dress. Also "That's something new, a dishwasher wearing a dress, that's new to the kitchen." -I was the only girl who worked in the back, all other girls worked in the front. Then my gender difference at my job became very apparent.
"Wow, that woman always wears a dress. Do you think she's in a religious cult?" - Response "yeah, I think she's a married polygamous momorman" - this was always overheard at work. Literally people assumed I was a mormon sister wife because I like long skirts.
"Who are you trying to impress every day when you get dressed up like that?" - this was in college when I was walking from one class to another.
"Do you have to wear a dress every time? Everyone's wearing pants. Do you always have to stick out?" This was at a family gathering.
One time I was approached by a stranger who offered me 300$ for sex, he thought I was a prostitute. I was wearing a unisex T-shirt that said "UC Berkeley Mathematics" and a long, ankle- length skirt. When I told him I wasn't a prostitute, he told me I should watch what I put on every morning.
I've also heard "are you trying to attract boys by wearing a skirt? because they aren't into that anymore, it just looks weird." - this was again in college, no I wasn't.
There's been countless times when I have been the only woman not wearing pants, or the only person wearing skirts in a room full of men, thereby my skirt accenting my gender difference, and people made me know it.
In elementary school boys would go around and flip up girls skirts as harassment and told us we were asking for it, by wearing skirts.
I even recall a law being cast as a teenager, where a man inserted hidden cameras in the pavement and took pictures up women's skirts and posted them on the internet. In the 90's after going to court it was deemed legal (I think it's been revoked since) because women were choosing to wear skirts and dresses in public.
I've been accused of being to formal in casual occasions, trying to get attention, obsessed with "being pretty," making a "statement," being super religious, hating my body, not "caring about my appearance", being insecure, being to confident, ,etc.
A friend of mine once told me in his native country they had discouraged girls from wearing skirts and dresses because there was a rapist on loose and they felt wearing skirts made it easier to be raped.
I've also heard the "easy access" joke way more than I wanted.
By the way, I LOVE wearing skirts and dresses and will keep doing it. And I hope you too enjoy wearing them as much as you want. But please know many of us have been harassed from a young age for wearing them and don't always want to carry that weight, and that's okay. My own girlfriend, who happens to be trans, was even criticized herself for wearing a dress at Christmas, being called out for "needing to prove her femininity" all the time by her aunt. Which is awful. But that's what happens.
But the point is, people often find the need to police what women wear, including skirts. Plenty of people will harass women who wear skirts, they will also harass without them. I can see how moving into a college dorm is more a laborious physical labor task, one where wearing something more practical like jeans and a tank top might make sense for practical reasons. it's not really an event where you want to look your best, you're just trying to move your stuff and say goodbye to your parents. I would probably go for comfort over looking nice. The kid in the red dress was probably just so happy they could be themselves and that was more comfortable for them. Good for them. But also good for the girls in the cool tanks and jeans. It was probably hot and they had a lot to move. Many will probably wear a cute sundress to their first day of class.
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