Post

I Like to Wear Skirts

Personal Stories, Advice, and Support 1,943 People

    This Is A Vent

    sorry to wright this here but i love skirts and dresses. all i hear from some people is that this is wrong but i would like them to think about the first person to wear pants i think people gave them a hard time. i still need some one to tell me when it was decried that only...
    spaz1177 spaz1177 46-50, T 4 Responses Jul 9, 2013

    Your Response

    Cancel

    Today was weird. I had a normal Monday.

    Up early, Got to work did my job came home. Once home had to take my daughter to guitar lessons then swim team. All the while wearing my heeled boots and skirt. Of course my skirt is still worn under my jeans. I know it's there, but no one else does. My wife went to a...
    shadowplt shadowplt 46-50, M 2 Responses Mar 31

    Your Response

    Cancel

    My English Teacher Always Says

    Essays are like skirts, long enough to cover the point, short enough to make it interesting. ;)
    zeezee669 zeezee669 16-17, F 2 Responses Nov 11, 2013

    Your Response

    Cancel

    Today was a first for me.

    I went out wearing a skirt and heeled boots. Kinda scared me. It was a knee length black bell shaped skirt with black 3" heeled boots. Didn't spend much time outside my truck. Just enough to towel dry it after washing. Felt scared and exposed, yet at the same time exhilarated...
    shadowplt shadowplt 46-50, M 2 Responses Feb 14

    Your Response

    Cancel

    Yes I do.. Very much so.

    I love to show off my long sexy legs in short skirts. I do have some long skirts but don't wear them all that much. Most of the time I'm wearing a short skirt or dress with my 5" heels and pantyhose or stockings. No matter what time of the year it is. I like when my legs are...
    TiffanyMarieLeggs TiffanyMarieLeggs 51-55, T 2 Responses 5 days ago

    Your Response

    Cancel

    To my circle, I've added a couple of photos of

    myself in dress. Feel free to view and comment.
    shadowplt shadowplt 46-50, M 1 Response Mar 16

    Your Response

    Cancel

    Some times it's fun to walk the dog wearing a

    skirt, hose and heels. Didn't get to do that tonight. Just walked the dog. Tonight I get to watch tv, and get up early. Rinse and repeat.
    shadowplt shadowplt 46-50, M 3 Responses Mar 24

    Your Response

    Cancel

    For the past few days I've been wearing my 3"

    heeled boots around town. No one has said a word to me. The weird part is I think I'm more conscience about it than others. The click of the heel and toe resonates more to me. I'm liking the feel of the higher heeled boot. It's comfortable. One thing I did to make it better was...
    shadowplt shadowplt 46-50, M 2 Responses Mar 12

    Your Response

    Cancel

    Another new experience today.

    .... Had to be in a Very public place all day. Wore my short boots, dress pants with a skirt underneath, boy shorts and a nice dress shirt. It was obviousness what I was wearing. No one noticed.
    shadowplt shadowplt 46-50, M 11 hrs ago

    Your Response

    Cancel

    Another day blog. Went to work

    and had a short day. Got home early and had the chance to be home alone. Well you know what that means, Skirt time! Got to spend a few hours alone dressed and booted just doing stuff around the house and yard. Felt kinda nice to just not worry about being responsible for...
    shadowplt shadowplt 46-50, M 2 Responses Apr 3

    Your Response

    Cancel

    Tonight I went out. I wore my skirt,

    heels boots and just walked around the local walking trail. Felt scared as I passed couples and runners. But felt as myself wearing a skirt and boots. Wasn't wearing a wig, makeup or anything Femme just me. Nice to be just me
    shadowplt shadowplt 46-50, M 4 Responses Mar 13

    Your Response

    Cancel

    The other day I was wearing some nice work

    clothes, hose and scrub shoes. My wife commented that the shoes were too casual for my attire. Went to breakfast then looked at what I was wearing and felt the same. Under my dress pants I wore a skirt and boy shorts (my preferred underwear). I thought, I need some boots...
    shadowplt shadowplt 46-50, M 1 Response Apr 8

    Your Response

    Cancel

    The More Intricate And The Bigger The Better

    As a cross dresser I love to wear a skirt to relax in when I can. I have always admired the way pleated skirts swirl when the wearer walks but I also enjoy the way many modern fashions use skirts which have cleverly designed panels often cut on the bias in order to add to the way...
    joanmcarthur joanmcarthur 56-60, M 4 Responses Jun 7, 2012

    Your Response

    Cancel
    1234Ideclareathumbwar 1234Ideclareathumbwar 18-21, F 2 Responses 5 days ago

    Your Response

    Cancel

    Mondays are for the dogs.

    ....I had an early show to work today so I wore my boots into my desk. No one else was around which made me feel "safe" to click clack down the halls. Took them off to do my job. I have to do a lot of walking to get into the simulators and teach. Had to figure a way to get them...
    shadowplt shadowplt 46-50, M Mar 17

    Your Response

    Cancel

    Went to the downtown area last night.

    It's an event called First Friday. The downtown square opens its doors for shopping, dinning and socialization. Fun event: music (a band played good country music) food and lots of people mingling. They held a charity 1k walk and 5k run. A lot of the women were wearing running...
    shadowplt shadowplt 46-50, M 1 Response Apr 5

    Your Response

    Cancel

    I Love 'em!

    I always wear skirts; for our uniform, when I go to the mall, etc. etc. etc, I always wear them! And I also wear them very short. In fact, they are so short that boys always try to see under my skirt downstairs. Who cares? They are great! lol
    experiencegirl733 experiencegirl733 13-15, F 2 Responses May 14, 2012

    Your Response

    Cancel

    Last night went to a mall store to look

    for dress pants for work. Found a pair in the women's section that look a lot like guy dress pants only they have a tapered leg towards the ankle. Wore them to work today and no one said a word. Very light weight (great for hot weather) and silky on the inside. Felt great...
    shadowplt shadowplt 46-50, M 2 Responses Apr 2

    Your Response

    Cancel

    So Versatile

    I find dresses and skirts so feminine. I could wear both for almost any function. Skirts are especially good for work as they not only look professional but you can show off some very special blouses and tops. Skirts come in many shapes and sizes. Although I'd love to wear...
    Josie06 Josie06 56-60, F 7 Responses Sep 30, 2008

    Your Response

    Cancel

    Yesterday I went and took a bunch of pictures

    of being out and about. Kinda scared doing this but at the same time fun to do. I'll try again on another day.
    shadowplt shadowplt 46-50, M 1 Response 5 days ago

    Your Response

    Cancel

    The shorter the better.

    I have a collection of schoolgirl skirts, and I wear them mostly with kneesocks, and tights at times.
    schoolgyrlKaren schoolgyrlKaren 41-45 4 Responses a week ago

    Your Response

    Cancel

    Springtime is almost here!

    I love warm weather and a short or mid length skirt is the perfect thing to wear on a warm breezy spring day. I love having my legs un-covered after being stuck in jeans and pants all winter, and I love to feel the wind and the warmth of the sun on my knees. Also, I have to...
    shygirl214 shygirl214 18-21, F 5 Responses Mar 24

    Your Response

    Cancel

    I think today I'm going to get a little braver

    and go to the drive-thru en Femme; again without make-up, wig etc.
    shadowplt shadowplt 46-50, M Mar 14

    Your Response

    Cancel

    Skirts are My Favourite

    I love to wear a skirt. Since I started to explore cross dressing I tried and liked the look and feel of my mums skirts on me. I still love them and put them on when ever I can. I wear them at home and I wear them when I am out as Vanessa or when I got to my transliving club...
    Vanessacd1957 Vanessacd1957 51-55, M 7 Responses Dec 6, 2011

    Your Response

    Cancel

    Today I was able to get off work early

    and wear my skirt and boots. I wore the skirt in my truck and hid it when running errands. Still skittish about being open with a skirt. Boots are a different story. Getting comfortable with wearing them around town. Get some weird looks occasionally, but no comments or glares...
    shadowplt shadowplt 46-50, M 3 Responses Mar 26

    Your Response

    Cancel

    Went out again tonight wearing my boots

    and and just above the knee length black and red flare skirt. This time I took my truck to wash my grill pans at the quarter car wash. I decided to take my jeans off as I washed the pans. Amazingly no one noticed. I was proud that I could be "out" and feel comfortable. Still...
    shadowplt shadowplt 46-50, M 3 Responses Feb 19

    Your Response

    Cancel

    Learning something new each day.

    Today I started to figure out that John Q Public ( most of them anyway) really couldn't give a rats A_ _. What you wear when out and about. Some will Lear, make funny faces or chuckle to their friends, but most just don't notice or care. They're too busy with themselves and...
    shadowplt shadowplt 46-50, M 3 Responses Mar 14

    Your Response

    Cancel

    Added some new photos

    and am working on more.
    shadowplt shadowplt 46-50, M 5 days ago

    Your Response

    Cancel

    I Like To Wear Skirts

    I started dressing at 10, I would mostly wear button front skirts, blouses, cardigan sweaters and white socks and would walk to the park or mall. I loved the looks I would get, not a lot of girls even dressed that much like a sissy. It was both fun and scary at the same time...
    wantobeinskirts wantobeinskirts 26-30 4 Responses Jul 18, 2011

    Your Response

    Cancel

    I Love My Skirts

    From maxi's, to mini's, to denim, to high wasted, to colorful I have all the skirts you can imagine! My favorite are the high wasted skirts. I have 4 high wasted, 6 mini's, 3 denim, 5 maxi's, and 3 different colored denim (pink, ombré orange, and ombre green). Skirts make me...
    Fieldhockeylover Fieldhockeylover 18-21, F 2 Responses Jul 9, 2013

    Your Response

    Cancel

    Finally the weather is warming up.

    ...time to break out the skirts! My purple jeans mini is the first one I will wear.
    Brandie1960 Brandie1960 41-45, M 6 Responses Apr 1

    Your Response

    Cancel

    Yes I Do At Times

    I find nothing wrong with wearing a skirt at times.  I find that especially during the summer months it is a lot cooler than jeans and a tee.  I know it isn't always practical to wear a skirt but there are times that I get a little flirty when wearing one.  I know...
    deleted deleted 26-30 2 Responses Sep 28, 2008

    Your Response

    Cancel

    Yesterday was a fun day

    for me. I had a long day wearing my skirt, boots and have added hose to the ensemble. Really liking the feel of hose on my shaved legs. Kinda silky, kinda smooth. Keeps the legs warm when there's a chill in the air. The only thing I don't like is the wisp feeling of a slight...
    shadowplt shadowplt 46-50, M 3 Responses Mar 23

    Your Response

    Cancel

    This evening I went out shopping guy style.

    ...I know what I'm looking for and don't want to spend a lot of time doing it. Went to a discount clothing store looking for boots(women's), skirts and some jeans. While in the women's section looking at a skirt, the sales lady (really a young lady) came up to me and asked if...
    shadowplt shadowplt 46-50, M 4 Responses Mar 29

    Your Response

    Cancel

    I Love Shopping!

    Yesterday my wife and I went shopping at our local KMart. I like Jacklyn Smth fashions, maybe 'cause I watched her on Charlies Angel and liked her clothes then. Anyhow, we found huge mark downs on everything! Tops, suits and SKIRTS!!! At $5.00 each I could have easily blown our...
    leggsqueen leggsqueen 56-60 4 Responses Mar 4, 2012

    Your Response

    Cancel

    Got up early today due to

    once again having to be into work early. Slipped on my skirt and work clothes, finished my hygiene routine and took off. Wore the hoes under my pants and was comfortable as all get out. I've tried hose that cover your bottom and found them to be too hot and with boy shorts...
    shadowplt shadowplt 46-50, M Mar 19

    Your Response

    Cancel

    Interesting day yesterday .

    I spent the day wearing knee high hose and regular shoes. (For me regular shoes are what's called "Scrubs") Too cold to wear shorts so I wore jeans a tee shirt and hoodie. Went to a movie with my wife (Divergent). She either didn't care or didn't notice the hose. It felt...
    shadowplt shadowplt 46-50, M Mar 24

    Your Response

    Cancel

    So today I was wearing my boots out

    and about running errands after work. I got a weird look from some ladies older than I am. One walked over to me and asked,"Young man, why do you have ladies boots on"? My reply to her was that they're comfortable and I liked the look. Then I asked her, "And why do you have on...
    shadowplt shadowplt 46-50, M 1 Response Feb 27

    Your Response

    Cancel

    Discovered the good feel knee high leggings

    (hose) are on your legs. My boots slip on better, they are cooler against my jeans than socks and they're comfortable.
    shadowplt shadowplt 46-50, M Mar 18

    Your Response

    Cancel

    I discovered something yesterday.

    ...it's fun to bowl in a skirt, even if it's under jeans. I was also wearing hose instead of socks. Makes the bowling shoes more comfortable.
    shadowplt shadowplt 46-50, M 2 Responses Apr 7

    Your Response

    Cancel

    Today I discovered something.

    ... People don't care what you wear. They care more about the norm and the stereotypes of society. Went out wearing a floral skirt and boots this evening. At a convenience store filled my truck and no one batted an eye lash. Felt scared and thrilled at the same time.
    shadowplt shadowplt 46-50, M 1 Response 1 day ago

    Your Response

    Cancel

    Been wearing my flat boots

    and skirt to work in the past week or so. No one has said anything. Of course I have on guy pants and shirt, but the boots are definitely not "male" gendered. Also been wearing mascara and a light lip color. Again no one's said a thing. Kind of amazing to me that it's not...
    shadowplt shadowplt 46-50, M 1 day ago

    Your Response

    Cancel

    Had some time before work

    and went to Walmart to get shaving cream. I shave every day to keep from getting stubble legs and chest. Started shaving my arms too. Legs and chest for years. Anyway, while there I ran across some thigh high black hose and decided to try them out. Wore them at work for a...
    shadowplt shadowplt 46-50, M 3 Responses Apr 10

    Your Response

    Cancel

    I had the opportunity to wear my high heeled

    boots around town today. Jeans and a sweat shirt accompanying them. To my real disbelief I again got no comments. A few stares and curious looks, but nothing else. Right now I get about and hour at home alone. I call this my "Boots and Skirt" time. Again I don't do make-up...
    shadowplt shadowplt 46-50, M 2 Responses Feb 26

    Your Response

    Cancel

    ;-( leggings decided to rupture at the toes.

    Had to get a new pair. Bought knee highs and thigh high. Have to admit, thigh highs are comfortable and cover enough leg to look good and not warm the butt.
    shadowplt shadowplt 46-50, M 1 Response Mar 20

    Your Response

    Cancel

    Skirts And Dress Are The Bomb

    I too preferre skirts over pants or slacks, next to a pair of cleanly waxed legs, there is no comparison when the soft lining of the skirt rubs against your bare or pantyhosed legs. It definately shows of a cute blouse as well. But dresses are an easy solution to something to...
    MaryAnn4665 MaryAnn4665 46-50, M 1 Response Oct 17, 2011

    Your Response

    Cancel

    Related Experiences

    I want to try wearing skirts but I cant :(
    lostgirlboy lostgirlboy 22-25, M 1 Response Apr 5

    Your Response

    Cancel
    I do not like wearing a bra but I do because I need to these days. I need to give my girls a break from captivity.
    ebonynbill ebonynbill 26-30, F 2 Responses 3 days ago

    Your Response

    Cancel
    Of Petticoats and Parking Lots When I got married in 1987 the retro fashion of crinoline petticoats had just come into style. I loved the look and comfort of wearing three white...
    BadPam BadPam 51-55, F 3 Responses 2 days ago

    Your Response

    Cancel
    The common clothes i love to wear, i literally have a walk in closet full of skirts and dresses. My reason for loving to wear dresses is that it not tight on the body like jeans...
    NymNin NymNin 18-21, F 3 Responses Mar 19

    Your Response

    Cancel
    One Sunday I wore a purple dress to church. It was nothing special but it looked nice. After church we went into the Commissary to get a few groceries. We were checking out when I...
    SweetMae SweetMae 56-60, F 28 Responses Mar 21

    Your Response

    Cancel
    I love wearing tights and pantyhose but I've always questioned one thing about it... Is it bad for me to have it? Bc I can't help it.. I love wearing them and having them but is it...
    cameron20 cameron20 18-21, M 8 Responses 4 days ago

    Your Response

    Cancel
    Alright so I took some of your advice and I decided to whale tail at my friends house. Three of us were watching Titanic and I was wearing these super thin material white sweats...
    annabanana95 annabanana95 18-21, F 3 Responses 1 day ago

    Your Response

    Cancel
    Love dresses! 💜 I grew up in a family mostly of ladies. I was 6 when I was put in my first dress by my cousins. I was embarrassed then but I really liked that experience. Since...
    sissyyumi sissyyumi 22-25, M 5 Responses Apr 11

    Your Response

    Cancel
    Today I'm wearing a tight red dress, it is such a great fit and look lovely. I really like the tight clingy look and look forward to seeing my friends reactions :) My only worry...
    LucyTG LucyTG 26-30, T 3 Responses Mar 20

    Your Response

    Cancel
    Good I wear women's underwear pantyhose dress heels I love it
    astroboy4545 astroboy4545 61-65, M 4 Responses Mar 21