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

Personal Stories, Advice, and Support 699 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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    there no question, I much

    rather prefer dressing in skirts, I just prefer dressing like the woman I am :-)
    EricaDress EricaDress 41-45, M 4 Responses Jul 5

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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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    I have no preference.

    That said a friend of mine said "Dresses for me are like a big fabric hug, Skirts are a statement about how you feel. Makes no sense to me but I am sure it will to somebody
    deleted deleted 26-30 2 Responses May 20

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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 2 Responses Jan 27, 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 2 Responses May 15, 2013

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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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    On the whole, I prefer a skirt

    and blouse. I think it's more fun to undress someone you are seducing when there are more garments. I also love the half-dressed look, whether top or bottom. On myself, I don't know. I don't have any dresses and only a few skirts, partly because dresses cost more and are harder...
    tyrihans45 tyrihans45 66-70, M 7 Responses Apr 14

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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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    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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    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 4 Responses Jan 27, 2013

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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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    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 Mar 21, 2011

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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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    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...
    0hBrandie 0hBrandie 41-45, M 2 Responses Aug 25, 2012

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    I Prefer Dresses

    I love wearing all female clothing but prefer dresses
    jeffw24 jeffw24 46-50 2 Responses Sep 16, 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 1 Response Mar 2, 2012

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    I Prefer......both!!!

    When I am out in my male self mode, I love to look at women, checking what they are wearing. I think a woman can wear a skirt and blouse and be very attractive. I really love to see a fit woman wearing a form fitting mini dress. Woman dressed in business suits, skirt and jacket...
    davis36a davis36a 61-65 Nov 21, 2011

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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 66-70, M Dec 21, 2012

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    To me, dresses are definitely more feminine.

    Sometimes a skirt just seems to be almost the same as pants, done up at the waist. Of course, if they are very tight and straight, that helps to make up the difference.
    57Peggy 57Peggy 56-60, M 7 Responses Jun 20

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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 1 Response Feb 29, 2012

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    Honestly, I do not have a preference one over

    the other. I like them both equally. Formal skirts are great for suit tops, and formal dresses for formal parties. Mid-length skirts and wedges are a great way to dress up casual tops for a night on the town. Casual Dresses are for going out during the day. Nicer dresses are for...
    Yoshi9ist Yoshi9ist 22-25, M 3 Responses Oct 23, 2014

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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 3 Responses Apr 18, 2011

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    I was in male mode but had all my girl under

    clothing on. I went looking for a new skirt. I tried on some in one store and then went to the next. I found a white pencil skirt that looked nice. I went and tried it on and it was just what I was looking for. I but my regular clothes back on and went to pay for my skirt. The...
    mat2Robin43 mat2Robin43 51-55, M 12 Responses Apr 8

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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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    Decisions Decisions...

    I really enjoy both. When I first began dressing up, I was attracted to dresses. They are so elegant, and feminine. Once I started to wear skirts, however, I began to appreciate their flexibility. With respect to fit...I think skirts are easier for crossdressing males to...
    BizSuitStacy BizSuitStacy 46-50, T 5 Responses May 5, 2011

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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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    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 25 Responses Dec 18, 2010

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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...
    57Peggy 57Peggy 56-60, M 4 Responses Sep 26, 2013

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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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    Dresses

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

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    Dresses For Me

    I occasionally wear skirts with a nice satin blouse just for a change of pace, but there's something all-encompassing about having the silky material wrapping my whole body up from shoulders (or even from the neck) down to my feet.  A dress that has a back zip so you can't just...
    CDralph2010 CDralph2010 46-50, M Jul 20, 2011

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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 66-70, T 6 Responses Aug 30, 2013

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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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    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 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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    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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    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 4 Responses Jun 10, 2011

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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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    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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