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I Wonder, Do You Prefer Skirts Or Dresses As A Male

Personal Stories, Advice, and Support 705 People

    Prefer Dresses But Skirts Are More Practical

    I like dresses because they feel good to wear. They express my femininity better, too. However, it's kind of difficult to find dresses that look good on my tall and typically male-shaped body. It's much easier to find skirts that look good and so I more often end up wearing a...
    davina1407 davina1407 56-60, M 1 Response Aug 30, 2013

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    I Like Dresses Best..;-)

    I prefer dresses.The thrill of stepping into a dress and drawing it up over my body then closing the back with a zipper or button is so feminine to me as male clothing is pull over or front closer. But I do have some skirts for variety which is pretty none existant for males to...
    angiecan angiecan 51-55, T 27 Responses Dec 18, 2010

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    Skirt Gurl

    Oh, I'm a skirt gurl for sure. I wear short denim skirts in the summer when my wife and I are camping in our RV. Getting gas, going to the grocery store, it's fun. Only once have I gotten bad looks, that was in a small town in Idaho at a grocery store. The clerk and the woman...
    sissyallison sissyallison 61-65, M 2 Responses May 24, 2012

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    I Love Skirts

    I do prefer wearing skirts: lots of materials, length, and design. but dresses are good to
    Sophietrav Sophietrav 51-55, M 1 Response Sep 4, 2012

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    I Prefer Dresses

    I love wearing all female clothing but prefer dresses
    jeffw24 jeffw24 46-50 Sep 16, 2013

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    Skirts For Me

    I have a few dresses, but the fit is difficult. I seem to be size 18 around my shoulders and breasts, that are far too tiddly for this size bra. However, I fit 14 to 16 waist down, even with my middle sized middle. So, would love a swishy dress, but really enjoy skirts, in the...
    Moddle Moddle 61-65 1 Response Jul 16, 2012

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    Skirts

    i have 7 skirts and one dress SKIRTS ABR WAY BETTER
    snessy snessy 31-35 13 Responses Jan 15, 2011

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    Dresses

    I would have to admit that I prefer dresses.
    wolfordlover wolfordlover 41-45, M Jan 1, 2013

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    A Little Of Both

    My preference depends a little on my mood, or what I am doing. Most of my dresses are around knee length, but most of my skirts are shorter.
    crystalkid crystalkid 41-45, M 1 Response Aug 11, 2012

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    None

    prefer skirts and blouses but do not mind dresses if they are short and tight eneough
    audraday audraday 46-50, M 2 Responses Apr 18, 2011

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    Nerves

    I wear dresses at home. Would love to wear dresses in publuc. Need advice on what to do to go public.
    cdlisa1963 cdlisa1963 46-50, M Feb 29, 2012

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    I Love Long Dresses!

    I love dresses, especially long pink dresses. But I do like to wear black skirts with a nice top too and some pantyhose tights. Usually brown tights.
    Natalie121 Natalie121 18-21, M 1 Response Jul 21, 2011

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    I Changed Over The Years

    When my mother first dressed me as a girl I really loved wearing my dresses. Along with the crinolines and petticoats, they came in all the pretty colors. With boys clothing you were really short changed between black, tan, navy blue or jeans for bottoms. usually depending...
    Melodie13 Melodie13 61-65, M 5 Responses Dec 14, 2010

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    Trying On Skirts For The First Time

    A while ago with Melodies encouragement I went to Goodwill and tried on a few skirts while I was there. I was very nervous because I was doing something very new to me. I knew my skirt size to be an 18 or a 20, so I looked through them and found a few of them. I then took them to...
    andreaneejustinfield andreaneejustinfield 41-45, T 8 Responses Aug 12, 2011

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    Lean toward Skirts AS a life-long cross

    dresser I love anything with a skirt. While I love wearing a nice dress, skirts provide so many more options. I own one pair of female pants - ones do one would ever mistake for male - and two pairs of female shorts - a skin tight denim pair and a loose legged pair.
    cdsubalice cdsubalice 56-60, M 3 Responses Dec 5, 2013

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    Love Pencil Skirts

    I love dressing in anything female but my absolute favorite is a pencil skirt. The longer the pencil skirt the better.  I love the way a pencil skirt restricts my steps when I walk and the feel of the skirt rubbing on my stocking covered legs each time I move.  I do wear...
    KimmiCD KimmiCD 41-45, T 3 Responses Jan 27, 2013

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    I Love Short Skirts And Dresses!

    I love them both as long as they are short silky or satiny and show off your legs!
    wjk1849 wjk1849 46-50, M Dec 30, 2012

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    Well That Depends

    What I prefer depends on what mood I am in or what I am going to be doing. If I am going to do some cleaning of the house then it is a dress. If I am just picking up and straightening up then it is a skirt. If my mood is wanting to be sexy then shorter skirts with body trimmers...
    Adam59 Adam59 56-60, M Dec 13, 2012

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    I Love Skirts

    Well I love anything girlie and feminine, but I do prefer skirts. I like pleated wool skirts best. For me the perfect outfit is a plaid schoolgirl style pleated wool skirt and a fluffy sweater with a nice pair of heals.
    bethanngirl bethanngirl 56-60, M 4 Responses Dec 29, 2012

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    My Weakness Is The Sundress

    I don't know what it is about them. I personally think a sundress of a short but, respectable length is much more attractive than a hooters uniform could ever be.
    JonLotto JonLotto 26-30 Apr 27, 2012

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    When I Was A Male

    I wore both skirts and dressess, preferred dresses, but skirt were better for that polished look. as a size 12/14 top and 8/10 (uk sizes) bottom some dresses fitted ok, but most did not hage of my hip all that well. Now that I am no longer a male, I have developed a small amount...
    balleteunuch balleteunuch 41-45, T 4 Responses Nov 18, 2012

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    Dresses, Definitely

    I prefer the look that a dress gives, they just seem so much more feminine than a skirt and blouse. Having said that I actually wear more skirts than dresses because it is easier to find a skirt and blouse to fit than a dress because I like dresses with sleeves - even if they...
    teather teather 46-50 2 Responses Dec 19, 2010

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    I Love 'skirts For Men

    I love to wear skirts but as a man. Not to crossdress. I do not care for dresses as they as too feminine. I look for knee length and long ankle length skirts that are not feminine looking. I especially like the denim, cord, straight pencil and wide pleated skirts. I...
    sandy2915 sandy2915 56-60, M 5 Responses Sep 12, 2012

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    Dresses More

    I prefer dresses more than seperate skirts and tops even though i have skirts and tops. There are more dresses in my collection and i find them easier to put on. I prefer full skirted or pleated dresses because i love the freedom rather than a skin tight dress. Of all the dresses...
    gownlover gownlover 56-60, M 2 Responses Jul 13, 2011

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    It Depends...

    ...but if I have to choose then pass me the dress! I love how they feel over my body, ideally nipped inat the waist with a lovely wide skirt. That said I adore pleated mini skirts because they show my bum off nicely! Or was the question what do I prefer on women ;) Jo xxx
    deleted deleted 26-30 4 Responses Apr 18, 2011

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    Skirts

    do to the size of my body have a hard time finding dresses that don't look like tents. with a skirt i find i can have a nice skirt and top to make me feel better about my size
    spaz2692 spaz2692 46-50 1 Response Jan 8, 2012

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    I Prefer A Skirt

    I like both but usually go for a skirt because they are easier to size and match up with a blouse or nice top. I find it harder to fine dresses that fit right and look good. I like a knee length denim skirt in the summer and long skirts in the winter. Either a skirt or dress...
    NitaCD NitaCD 61-65, T 7 Responses Aug 30, 2013

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    Everyday Wear

    lovely long flowing dresses are my favorite but if I can't wear that then its into black tighs , jeans and a skimpy top and off down to the shop!
    christinemelody christinemelody 56-60, T Mar 2, 2012

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    Not Sure....

    I am a size 16/18 on top and size 10 on the bottom So finding a dress that actually fits well is very hard and as a result I don't have very many dresses. I never stop looking for that great fitting one or the perfect little black dress. But skirts I have no problem finding one...
    Brandie1960 Brandie1960 41-45, M 2 Responses Aug 25, 2012

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    Skirts

    My preferance is skirts. Dresses would be great but the cut of them is not quite right. Arm holes are a bit off etc.
    maninfl maninfl 70+, M Dec 21, 2012

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    Skirts

    i prefer skirts as i have to wear a size 20 top but a size 14 skirt so any time i get a dress the bottom is a little large but i have a few dresses that i like
    PoppyAnn PoppyAnn 56-60, T 1 Response Mar 21, 2011

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    I Prefer A Skirt

    For me I find it kind of hard to get dress that fits my upper body right and it's alot easier to match a skirt to variety of shirts tops and blouse you can even wear skirt with a hoodie or your wife beater t shirt
    notech64 notech64 41-45, M 1 Response Jan 16, 2011

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    Skirts Are For Me

    I prefer skirts. I have crossdressed since i was 10 ( i am 56now ). Back then dresses would fit me pretty good becauce i was little. As i got older and bigger they were harder to get off in a hurry if someone came into the house. I would dress anywhere and anytime i could. I...
    cindyloulove cindyloulove 56-60, M 3 Responses Jan 2, 2011

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    What I Like

    i would rather be in a dress. but the size of my shoulders and upper body make it hard to find nice dresses that fit well. there fore i wear more skirts that fit my waist and can find nice tops in a lager size that work
    spaz1177 spaz1177 46-50, T Dec 30, 2012

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    Hippie Skirts

    I love long flowing hippie skirts. They are so fun to wear and they are super comfortable. I like being a hairy hippie girl. I am from California after all.
    Kiki31 Kiki31 31-35, M Feb 17, 2012

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    Dresses Are Skirts

    I like wear short skirts or dresses to show off more of my legs. Then when to wind blows my panty's show.
    Rossiebottom Rossiebottom 41-45, M 3 Responses Nov 9, 2013

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    Good Question.

    I have many of both. Dresses my wife has to alter the lower half. Skirts are buy and wear. If it hugs my body and is fem, I lust to wear it. Cheryl Anne Swanson
    sherrynpantyhose2k4 sherrynpantyhose2k4 51-55, T Aug 25, 2012

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    Put Me In A Skirt!

    First of all, I love anything feminine but my go-to outfit is a skirt, usually denim. Though I dress almost everyday, I often don't go to the trouble of makeup, a wig, or even a bra and forms. While working from home, I'll often just wear a t-shirt with panties, pantyhose or...
    skirtsandpantyhose skirtsandpantyhose 51-55, M 3 Responses Jan 28, 2013

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    I Prefer Skirts

    I like the feeling of having a waist so I prefer skirts. I feel a bit naked and vulnerable in a dress- although I haven't tried one with a belt. Might try that. 
    meganb1 meganb1 36-40, T 3 Responses Jan 27, 2013

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    Dresses!! Definitely!!!

    I only have 6 or 7 skirts which I rarely wear, 2 skorts, but I just counted 62 dresses in my closet (not counting several space bags with others in them.) Of course, I don't seem to have the proportion problems others have, being only 5'3" tall.  However, lately I have been...
    Pegg Pegg 51-55, M 2 Responses Sep 26, 2013

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    I Prefer Dresses

    I prefer dresses but on occasion will wear a skirt and blouse. I like to wear longer dresses From time to time I'll wear a tunic and a skirt.
    jml2000 jml2000 56-60, M 1 Response May 15, 2013

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    This Isn't About Me.

    My hubby would have to say, "Skirts"He doesn't have any dresses.  A dozen or so skirts, slips and a couple petticoats.  He has his, I have mine.  It works out better that way, we do our own laundry so we don't get stuff mixed up.  He wears them around the house, and out in...
    Rachael74 Rachael74 56-60, F 2 Responses Jun 10, 2011

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    Skirts Or Dresses ???

    I'm not excatly shure wich I prefer! Wichever I wear I love Short-slutty like! Like my nightwear--Baby dolls-not long nities! But, Im one of those gurls who just love guys to be very forward-comment& grab/fondle ect- Don't ask me--just do it! esp. in more public...
    jettys jettys 56-60 Apr 20, 2012

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