How to Wear a Mini Skirt!

Good day to you all, loyal readers! I hope you all are having a Happy Autumn. I wish you all are able to enjoy the magic and splendor of this beautiful season. Today I would like to dive right into the discussion; Mini Skirts!

I was always fascinated by skirts, particularly mini skirts and their ultra feminine style. I will never forget my first time trying one on and the wonderful feeling of wearing something that wasn't jeans or athletic shorts. It was a flowy black and white striped skirt that went right down to my knees, and I will always remember not wanting to take it off again. I knew right then and there that it was something I would not be able to live without in my life.

When it comes to outerwear, it is easily my favorite article of clothing. There is absolutely nothing as liberating as being able to rock a sexy mini skirt on a cool fall day. Luckily, there are infinite designs out there to suit your individual style. XDress has taken notice of the importance the mini skirt has on the feminine wardrobe, by adding a fair amount of options to their site. My favorite in particular being the recently added "Camo Mini Skirt", which has a very simple yet femme style in Black and Gray camo.

At least 5 days out of the week I wear a skirt, and during this time I have learned some great tips for you all on how to successfully and confidently wear one as a man. First off, you need to decide whether you want your legs shaved or not. Nothing is wrong with either, but I do prefer both the look and feeling of having smooth legs. This is especially true when wearing pantyhose or stockings, which I always pair with my skirts. The next thing you need to consider is the visibility of your manhood. You cannot wear a skirt out in public if your private parts are bulging out.

There are several ways to avoid this issue. The easiest way is to wear a loose style that does not compress, such as skater or a-line (the style of the Iridescent Skirt here at XD). However, there is nothing quite like the feeling of wearing a tight fitting mini skirt. The best way to make wearing one socially acceptable, is by wearing a top that covers your bulge. At this very moment I am wearing a tight black mini skirt, but my bulge is hidden as I am wearing a mesh tunic over my top/skirt. There are also skirts with cute ruffles, such as "The Frilly Petticoat" which would work beautifully as well.

The most important part of wearing a skirt though, is your confidence. You cannot be ashamed or anxious while wearing one, or else you will stand out for all the wrong reasons. Practice your walk, keeping your back straight and allowing your hips to sway, and everyone will take notice. Soon, men wearing skirts will be as normal as women wearing pants. Perhaps men will even be able to wear skirts in the office, just as women wear pantsuits. After all, skirts are much better suited to the male anatomy than pants ever will be! If you haven't tried one on, then you owe it to yourself.

It takes a lot of courage to push this envelope, but it is necessary if you truly want to be happy expressing yourself. Besides, nothing can compare to the fabulous combination of a mini skirt, black pantyhose, and high heels. There is nothing that makes me more confident than when I receive a compliment on my legs, which I never received before when they were covered by my dreadful jeans. 

So that does it for today! When did you first try on a skirt? What are your favorite styles? Have you ever worn one out in public? Tell me your stories!



I enjoy wearing stockings and garters. With a somewhat shorter mini. I be bee. Told my long legs look great in stockings and heels. I wish everyone would try and enjoy smooth shiny stockings just one time. I think most would enjoy the silky smooth feeling on your legs

Shanie August 02, 2023

Wearing a short Mini is easy. Especially when I have long slim legs I wear mini skirts to the park and mall all the time. Sometimes with stockings. But mainly with pantyhose. As a tall slim male I usually get some lookers and comments. Mostly how good my legs look 🥰

Shanie April 10, 2023

I love wearing a mini skirt. My favourite is a black leather mini (or is it micro?) skirt about 9 inches long, especially combined with tie side panties, which I adore. It can be embarrassing if the knot on either side undoes, and they fall to the floor!

John May 02, 2022

Great post! I’ll have to share this with my SO. His go-to method is usually to wear his skirts over leggings, but he might appreciate the other ideas.

JOSHUA March 11, 2021

Been wearing mini skirts for many years. Love to wear with lace trimmed panties, garter belt and stockings. Never wore out but with friends at home. I always felt sexy being dressed in my mini with my friends. They use to comment about peeking at my panties. My bf loved to see me dressed.

Seattle Bill December 31, 2020

The pink polka dot skirt with matching panties is a perfect way to sport a skirt! Received many looks at my combination while out recently! I think I will try to match my panties to the skirt as best I can going forward!

Scott November 19, 2020

Great story. The first time I put on a skirt was I guess about 16 years ago. Growing up I had always been into running and playing sports so I knew that I had sexy well shaped legs. My era growing up was the 80’s. I was into going to Rock concerts for my love of the music and as a bonus I got to see many hot chicks wearing mini skirts along with thigh highs. I just loved the site of a pair of nice legs with the tops of the thigh highs peeking just below their mini skirts. I’d have to say that at least for me there is nothing more sexy. Years later I got the chance to try on my 1st skirt. It was a stretchy Black mini that could be worn down to my knees or pulled up higher to show off more of my thighs. I was hooked ever since. Then what pushed it even more over the top is when I added a pair or white thigh highs and garter belt. I haven’t looked back since. I now own not several, but 32 skirts and who knows how many thigh highs. I do possess a huge line of gurly clothes from heels to panties to dresses to lingerie. I sadly must say that I have not ventured out in public dressed in any of my clothing. I did on Halloween a few years ago, but only to see a friend while she was working at KMart, then home. I guess I haven’t got the courage yet to not care what others think. I live in a small town with big mouths and this is where my daughter lives with my ex-wife and they don’t know. Small minded people can cause a bad living situation both personal and working. One day soon I will bite the bullet and venture out. I am hoping that it will be with some friends and not by myself. I thought I would share my story and who knows, maybe some good advice will come of it. I am most happy and comfortable when I’m sporting a skirt or any other feminine attire that I own at home. Thanks

Brian November 04, 2020

Hi Geoffrey

Fabulous story! Thank you for sharing that. A New York doll!

I miss exchanging chat on clothes and looks with CD friends – as well as dressing out with them in trans-friendly places. This forum provides a nice and much needed alternative under the circumstances though.

Continue to be your feminine self – or am I on the wrong discussion thread there?


Ally x

Ally October 16, 2020

Hey Ally, thanks for the response to my blog, very thoughtful. Yes, i understand the restraints of the padded panty, it made me my most feminine, but like you said whatever fits and you feel good in, then go with it. I like your idea of going out to the park in the camo skirt, that is so great!! Me, not into the camo look, but it is a nice outfit. I never went out into the “public”, but rather during my 20 years plus I was able to attend all types of crossdresser parties and get togethers. I belonged to wonderful group crossdresser’s group in New York. We did all types of parties, shopping trips at selected shops and just hanging out with one another in our best girlie outfits. I have to say that the gurl friends I had were just so fantastic. The nicest and most beautiful people. Of course we all had one thing it common, being our feminine best, but we all had a wonderful time together. I have never met another group of people like my crossdressing gals, who were so engaging, pleasant, and so helpful. Anyway, all the best and thanks for this blog site. Lets all be our feminine best!!!!

Geoffrey October 13, 2020

Hi Geoffrey

It sounds like you had great fun with minis when you were younger. I so agree with you about wearing what looks good on you. This applies to women and men as well as cross-dressers who may be both. All people are different shapes, sizes and colours, so different things will work well or not so well with different people. However, I suppose there is also the school of thought that says, “Who cares what anyone thinks. I’ll wear what I want!” And I can’t argue with that!

When I was younger I did try the tight fitting padded panty forms you describe. Together with corsets and too high heels I found them too restrictive and uncomfortable though. Being comfortable in what I wear is important to me. Speaking of which, I had a wonderful day yesterday going about my daily business underdressed and with a touch of jewellery on my wrist and neck. I had the xdress silicon forms in my bra too (which are very comfortable and discreet). No mini then, but I’m definitely tempted to go to the park in that xdress camo mini and top.

Have a nice day everyone.

Ally x

Ally October 11, 2020

Wearing a skirt, or even better a mini skirt is one of the sexiest and most daring adventures we XDress guys can do. It can be very rewarding and exhilarating to say the least. I was fortunate enough to wear and look good in my mini skirts while i was single and in my thirties and up into my early fifties. During those fabulous years, I had long shapely legs. I am six feet tall, all legs, and weighed 150 pounds with a 28-30 waist. So, how do we wear mini skirts? Well, I excersised my legs often to attain a shapely look and shaved daily. This was important. As a result, I only wore mini skirts, bare skinned, no stockings, when I was out and about with my gurl friends. To wear my mini skirt effectively, I also wore a panty with padded sides and rear for those sexy curves. These panties were tight so it also gave me a nice tuck up front with a smooth appearance. So with shapely legs and fitted panties I was able to wear my mini skirts with confidence and sex appeal. In addition, panty hose and stockings also help, as they do give shape to your legs. Try flared minis as well, they give a great look, I was so confident that I wore them very short, with my panties giving a peek out from behind. Today I am married with a wife who allows me to wear my panties, bras and lingerie, but no skirts, I am 60 today So, I hope my experiences and styling cues help. However, the most important thing to remember is to be confident and be who you are, and wear what looks good on you! Also getting support from friends is important as well. Being feminine is a great thing so embrace it and enjoy. I have and still do to this day. Good luck

Geoffrey October 10, 2020

Very good information! Love the Camo Skirt!

Scott October 05, 2020

Ally, I wholeheartedly agree. If XD could start a line of underwear that helps to compress, I am sure it would sell out immediately. Tight skirts are my absolute favorite and being able to wear them without a mesh cover up or cardigan that covers the front of me would he spectacular. I’m sure most of us can agree on this! -Nathan

Nathan October 05, 2020

Hi everyone

I had swung away from skirts for a while as I played down my dressing into a more ‘feminine man’ style rather than ‘female impersonator’. Just recently I’ve swung back to them again. I began with a knee length dress but now have shorter dresses and skirts in my collection. One of my favourites for going casual on a hot day is a short denim mini in an a-line style. I loved the xdress camo mini and crop top as soon as I saw them. They are definitely on my shopping list. I can see myself wearing those with white or camo sneakers and a frilly pair of undies.

I think most cross-dresser dreams begin with short skirts and high heels. As always, I would say that being able to move comfortably is important to me. As Nathan says,what you wear on top can be important too. It’s about the whole silhouhette, not just the skirt. Bat-wing tops can look good when worn with a tight mini as you can create a nice triangular taper from top to bottom. This is feminine and yet both uses and disguises a male shape.

On bulges – maybe xdress needs to provide a little more help there with a panty form that helps to smooth and hide? I love xdress panties, but then wearing a skirt or a dress, a little bit of help in that area would not go amiss.

Happy dressing

Ally x

Ally October 04, 2020

Being an older person (67 yrs old) I prefer a knee length or longer skirt or dress. In the winter I usually wear kaftans.

Paulena October 04, 2020

Welcome, Sam! Your comments were very well said. It is indeed very fortunate to find acceptance from a female companion, I too have hit the jackpot in the arms of a wonderful woman. To have that and to get to be yourself are beyond words. Stevie Yes, I definitely agree. To be noticed in a way that isn’t offensive has a better impact on strangers, and they can go home that day with a more positive view on it.

Nathan October 03, 2020

More on skirt wearing: i agree we as crossdressers need to push the envelope so that society knows we exist . This goes for heels nail polish make up and the like. We need to do it in a tasteful way and wear appropriate clothing else we stay in the weird category! Go to a 💅🏾 nail salon get your toes foot 🦶 done Wear a kilt umm i mean skirt Wear heeled boots 👢 We ve got to go out their and make our case AND support each other when the snickering 🤭 starts

Stevie October 02, 2020

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