What is it like to wear a skirt with no underwear?

Answer :-

Opinion 1:-

I'm more than qualified to answer this question because I didn’t wear underwear or panties for 12 years except when I was menstruating. It didn’t matter if I was wearing a skirt, a gown or trousers; no panties were underneath unless I was menstruating.
What is it like to wear a skirt with no underwear? Hmmm. It’s different, unique, interesting. You can go for it if you want… However, I think you’ll have a better understanding of what it’s like if you follow me on my ‘underwearless’ journey.

How did it start?
It all started in 2003 – my first year as an undergraduate. My cousin, some of her female friends and I had gone for a party. After the party, we rendezvoused at my cousin’s place since she was living off campus. She was living in a one room apartment that consisted of bedroom, kitchen and bathroom. We all changed in the bedroom and in that brief moment, I had a life changing experience.
While they were all chatting animatedly, I noticed that my pantie was different from every other person’s own. They were wearing strange contorted panties that left the back bare and left almost nothing to the imagination at the front. Since I had been a high school nerd who wasn’t fashion forward, I never knew such contraptions existed. My eyes popped open. What was this thing? I heard them say something about G-string and pant line and turned to see pant lines from my grandmama panties protruding from my trousers.
A few days later, I went on thong shopping. Thongs were my new fashion statement but they were highly uncomfortable; so I threw them away after one week. But the problem of pant lines had to be solved. This ushered in my underwearless journey.
No panties = No pant lines. Only exception: During menstruation.
How did it feel?
Some people think you’ll feel sexy if you strut around without undies. Well, yeah; if that’s your reason behind it but that wasn’t mine. I felt self conscious the first week or so. After that, it was normal and ordinary.
Will people know? What will their reaction be when they find out?
It depends on the clothing you wear. If it is dark colored, opaque or thick, it won’t show. If the clothing is translucent and light colored, it’ll definitely show. Funny enough, nobody ever noticed it when I was wearing a skirt or gown. This is because I only wear gowns that have thick material + skirt materials are usually thick and the light or translucent ones have lining. Trousers are a different story.
One day in 2009, I was wearing a short blouse on a white trouser and walking down a crowded street with a friend. Because I catwalk and swing my hips, people usually stare at me when I’m walking. I’m used to it. One guy kept staring at me and assessing me from head to toe. I kept walking till I walked past him. The next thing I heard was: “Oh boy, dis girl no wear pant ooo” meaning “What! This girl is not wearing panties.” I kept walking. My friend later told me that it was obvious that I wasn’t wearing panties. My answer was silence. I basically do what I want to do despite the consequences.
Some people will know based on the shape of the trousers. One day, my mum came into my room when I was fully clothed in trousers and a top. Prior to that time, she didn’t know about my choice to be underwearless. After taking one look at me, this conversation started:
Mum: You’re not wearing panties.
Me: No
Mum: When you don’t wear panties, people will know because of the shape of your trousers.
Me: (Silence)
Like I said, stubbornness is one of my virtues. But then, I understand why my mum said that. She didn’t want people to objectify or sexualize me because of my choice not to wear panties.
Female acquaintances and friends reacted in different ways. When they found out or when I told them…
Some looked at me in a condescending way. As far as they were concerned, I was sexualizing myself or at best doing it to attract the opposite sex in an unacceptable manner. Some were indifferent. Some were awed that I had been pulling it off for so long.
The reaction of male friends was universal. When I told them, they always asked the following questions:
What if the trousers tear in public? My answer: It’s not going to happen.
Do you also wear skirts and gowns without panties? My answer: (Varied)
Then they went on to advise me to wear panties for my own good. My ex-boyfriend insisted. I never listened until one day…
What if 'accidents' or wardrobe malfunctions occur?
First of all, I never wear clothing that the wind can blow upward. The result of that is embarrassing with or without underwear. I also always sit cross-legged when I am wearing skirts or gowns – courtesy of my mum’s grooming skills but that doesn’t stop wardrobe malfunctions.

In 2007, after graduating with my Bachelors, I went for the mandatory NYSC (National Youth Service Corps) in Nigeria. We camp in a state picked by the government for a few weeks where we wear the NYSC uniform and a sportswear for almost all the activities in the camp. The sportswear is white t-shirt on white shorts. 
I’ll never forget the look on that guy’s face because I’ve never seen that look before and after then. It was a mixture of surprise, instant horniness, realization and guilt. He was sitting diagonally opposite me and I’m sure he had seen everything. I quietly turned and sat down with a different leg position but that wasn’t enough to stop me.
Fast forward to 2015, by this time my ex-boyfriend had come into and left my life with the impression that my ‘malady’ was incurable. I had become more serious in my journey of trying to gain muscle mass which meant that I’ll work out and gain muscle mass only to lose 75% of it some weeks later. It also meant there were points when my clothes were too tight.  At those times, I refused to tempt fate and wore panties. One of those days, in June 2015, my trousers tore at the back in the middle of a crowded bus stop during the day. A lady saw it from afar and shouted it out to alert me. Luckily, I was wearing panties. It was the immediate cure to my underwearless state.
Right now I wear underwear... but who says my underwearless days are over. I could just be on leave. After all, I do what I want to do despite the consequences.

Opinion 2:-

It feels as though you're hiding a secret from everyone. On the other hand, you feel as though everyone can tell regardless of skirt length. It can also be liberating and feels extremely natural after the initial hour or so. 
Try it sometime with a long skirt and then move up if you dare and/or are skilled enough to not go promoting your goods while sitting or taking the stairs. ;)

Opinion 3:-

well,i don't know but why are you asking this question,specifically? like Wei Shen said,why don't you try it yourself? however,i do understand curiosity,perhaps you either can't or dare not,which is why you want to hear others' thoughts. I don't know,it's still a little bit weird.
i remember been a teen at the time,i used to hate tight panties because i also wore it with tight pants. I didn't actually wear panties when i wore jeans or leggings,but obviously i wore dresses and skirts so i had no choice. Shorts? pfft,i just sit with my legs crossed and hope no one sees anything. As i teen i never dared to do anything like that--especially when i'm going to school or out public,it feels like you're hiding a big secret and you're going to be exposed. One time i almost went out in a dress that flares up when you twirl around with no panties,i freaked the hell out. I was not ready to experience my Marilyn Monroe moment without panties,not now. So i quickly went back (home) and slipped in some. I've always wondered what would happen if i really did forget,and boy it's still scary.

Opinion 4:-

The problems include the wind blowing my dress or skirt up and when its my period.  
Actually, in summer its quite nice and feels cool and so much better than panty hose and panties that had to be worn in winter to keep warm.
But the risk of exposing too much is always there and so most people would only do so with a long skirt or dress.  With trousers, its almost not worth doing as you are covered up anyway and the feeling of fresh air around you doesn't really happen.

source :- quora.com