I’m writing this because I have been wearing skirts for 2 and a half years now. I’m a 29 year old guy. Do you have any tips or advice on what I could wear with my miniskirts so I can look more like a female?
There’s no right or wrong way to look like a girl. Girls don’t have dress codes. Girls don’t have to wear miniskirts or dresses or stilettos or lipstick to look like a female.
Really, it comes down to the skirt that you’re wearing. I wouldn’t pair a skirt that has a pattern on it (such as flowers or polka dots or houndstooth) with a top that also has a pattern on it. I don’t take a lot of fashion risks when I wear skirts. If I am wearing a skirt with a pattern on it, I will pair with a top with a solid color. Same thing with a top with a pattern or design, I’ll match it with a solid color skirt.
Black tops are USUALLY pretty safe when it comes to pairing with a skirt, too. Peplum tops are usually my go-to when it comes to skirts as they have a cute, flirty detail around the hips giving my body a curvier appearance.
Fabric matters too. Denim and leather skirts will go better with certain fabric and material as well. Of course it all comes to what you like and what you think looks cute. As I said, girls don’t have a dress code and should wear whatever they want, and that goes for t-girls too.
Solid color bodysuits are also a good top to pair with skirt and helps with the whole “do I tuck in my top?” dilemma.
I know I have some very fashionable readers, what are some of your tips when it comes to wearing skirts? Please let us know in the comments!
Because of this, my confidence is about zero when it comes to creating an outfit based around one. In some ways I feel that skirts and a cute top are a little… well, maybe casual isn’t the right word, but I tend to wear dresses that stand out pretty much anywhere. I am most comfortable in a dress and heels even if I am overdressed for whatever I am doing. I just like to look my best and I think I do when I am wearing a beautiful dress. The dresses I wear are a little more formal (if that’s the right word) compared to the casual dresses I see other girls wear out in the real world.
Please know that when I say I stand out I am not saying I am the prettiest girl in the room, but I am a six foot t-girl in heels. No matter what I wear I am not going to blend into the crowd.
The few times I wear a skirt it’s because I saw an outfit on a mannequin and I thought it looked cute, so I simply bought what it was wearing and wore it. And I am being 10000% serious. I do wear skirts from En Femme because their separates make it very easier to coordinate a cute outfit. But if left to my own devices I am pretty insecure about picking a top to go with a skirt. When I see girls wearing skirts, no matter the outfit, it always looks cute. But when I try something similar my insecurity hits a new level and I usually end up hating how I look. For one thing I can never tell if I should be tucking in a top with a skirt. I mean, I know it depends on the skirt and the top but I still feel pretty lost.
But every once in a while a skirt jumps out at me and I want to wear it. It could be a cute pleated skirt or a leather skirt and I suddenly become obsessed with it. Whenever the weather gets warmer I am drawn to jean skirts. I see girls matching them with simple t-shirts or cute blouses and they always, always look good, even when they are paid with sneakers. The cute/casual/comfy look is just not a look I think I can pull off. Besides, if an outfit doesn’t *need* heels I am zero interest in wearing it, lol.
Out shopping one day I saw a cute top that I thought would look good with a jean skirt. The top was dressy enough that matching the outfit with heels wouldn’t look out of place. So I bought it, along with a jean skirt. It was an outfit that I thought would look cute on any girl, even me. I tried it on when I got home and my confidence crashed. BUT! I expected that. Trying on an outfit in boy mode almost always makes me look terrible. It is a completely different outfit when I am wearing my thigh pads, my breast forms, and have my hair and makeup done. The outfit fit, it worked, and I decided to wear it one my next time out en femme.
My next time out would line up with a photo shoot where I had to review some fishnet stockings. I met up with Shannonlee and we took some pictures outside at a park in a couple of different outfits. Since the jean skirt outfit looked very summery it was a perfect location for it. She took some pictures of this ensemble and before I changed into a dress (yay!) I asked her to take a photo with my phone. I wasn’t thrilled with how I looked, but I knew there’s a world of difference between an iPhone camera and professional equipment. I didn’t let the picture crush my self-esteem (that much) and I moved on with the shoot.
Of all the photos we took that day, I was most curious how this outfit would turn out. I dissect every photo of myself and I look at what I am wearing, my makeup, and whether I look too boyish before I decide if I want to share the picture on my website. If it’s a good picture then I want to show it off, obviously. I clearly like doing that 🙂 but I am also willing to hear feedback on an outfit as to whether or not it works for me. I am often insecure and I admit compliments do a lot to pull me out of a funk if I don’t think I look pretty in a picture. I am shallow and honest enough to admit that getting Likes on a photo I post on Twitter does a lot for my self-esteem.
That being said, here are the photos of the outfit. I think they turned out okay but I am not sure it’s an outfit I will wear again (unless ya’ll think I should, lol).
I was asked to review a pair of stockings from We Love Colors recently. I love doing reviews and it’s a fun reason to arrange for a photo shoot. I spent some time picking out which stockings I wanted to review and of course, I HAD to pick fishnets. 🙂
I don’t wear fishnet stockings that often, they are more for a special occasion or when a dress almost demands it. At first I was skeptical about what on Earth I could say about fishnets beside the fact they are irresistible and sexy. They project an alluring sexiness and confidence that is pretty much unmatched when it comes to stockings. They are not for the timid.
So what makes We Love Colors stockings so different? The pair I chose were the Wide Mesh Fishnets and my first impression was the quality. Most fishnets FEEL cheap because they are cheap. They have a tendency to snag and tear more than any other types of stockings but these felt more durable. I wasn’t afraid of them tearing when I put them on.
Fishnets demand attention, they asked to be seen. They are not subtle. The color of the stockings seemed more black, seemed darker than other fishnets I’ve worn. These stockings, like everything else We Love Colors makes, were hand-dyed and I think it makes the black of the fishnets really pop.
We Love Colors is inclusive and transfriendly and make wonderful stockings. I absolutely loved how these fishnets completed this look and I can’t wait to pair them with my new corset dress at my next photo shoot.
Thank you to We Love Colors for these sexy stockings.
Occasionally you mention your love for leggings, praising their sexy look and comfort. I only once purchased leggings to give them a try but was disappointed with the wrong sizing, boring fabric and baggy look. I gave them to my wife without thinking twice. But I STILL want the experience of leggings YOU write about. Could you please give me some guidance on how to locate those stores that carry the brands, style, fabric and fit you love??
Like almost everything we shop for, leggings really require you to know your measurements, especially your waist and hips. I wear leggings in boy mode, never en femme so when I take my measurements for leggings I do so without my hip pads.
I wear a size 12 (or a medium) in skirts so I use that as my guide for leggings. Leggings are pretty stretchy so if I am between sizes on a pair I go for the smaller of the sizes. Length might be an issue for a girl like us, but I care more about the fit around my waist. The leggings I am wearing now go down just below my calf so I think it’s a good length for them.
I do have several pairs that I wear on a regular basis. I have the pair I am wearing now which is a nice, soft cotton blend. I have a pair of femme leggings I run in, but my favorite pair is a faux leather from En Femme.
This is something you may need to do some trial and error shopping with, but thankfully leggings aren’t too expensive. I get most of my leggings from Target which are about ten to twenty dollars a pair.
If we are all on a journey (and that word annoys me less than it used to for some reason) then our journeys are marked by milestones.
I think we all have pretty common milestones, significant moments and small accomplishments that show our progress. Some of the standout moments in my life include the first time I wore a bra, the first time I tried on stilettos at a store, the first time I left the house en femme, my first makeover… the list continues.
Of course, no one HAS to have these moments but I think (depending on where you are on your journey) many of us can recall similar first times. Do you remember the first time you woke up in a nightgown? I absolutely do.
Since so much of my gender identity is tied to clothes I mark much of my journey by what I wear. I used to wonder if I was transgender because I wore “girl clothes” or if I wore “girl clothes” because I was trans but I’ve decided that I was born this way and I just simply and absolutely love clothes. I love how a dress can boost my self-esteem, my confidence, and shape my whole day.
Many of these milestones are tied to what I want to, and what I want to wear. I had always wanted to go to dinner or see a play en femme and I’ve done those things. Crossed them off my girly “to-do” list. Clothes are not any different in that sense to me. When I was a kid I looked longingly, almost achingly, at the beautiful lingerie that the models in catalogs were wearing. I dreamt about how amazing it would be to wear stockings and a garter belt, along with matching bra and panties. There was (and still is) something so sensual, beautiful, feminine, and almost innocent in that elaborate lingerie.
I am at a point where I feel I have worn almost everything that I want to. If there’s something I want to wear, whether it is an evening gown or a corset, I shop for what I am looking for and usually end up wearing it for a photo shoot. As the list shrinks I find it to be a little… bittersweet. On one hand, I am beyond fortunate and blessed to have worn so many things on my wish list. On the other hand, clothes make me insanely happy and I love wearing something that I have always wanted to wear. It’s getting harder to think of new and fun outfits to wear for photo shoots. The list isn’t finished yet, but goodness it’s getting close.
Whether you identify as a crossdresser, t-girl, gender non-conforming, non-binary, or something else, there is a part of your journey where we can go from accepting (yes, THIS is who I am) this side of us to EMBRACING (yes, THIS is who I am and I LOVE it) this side of us. In my opinion the real fun begins once we make this step. Once I embraced who I was (and this was at twenty years old) then I let my imagination run wild. I let my inhibitions go. I started to buy and wear what I wanted. I mean, this was all done discreetly and in secret, but it was thrilling to shop for stockings after wanting to wear them all my life.
It’s not uncommon for there to be a link between this side of us (and what we want to wear) with eroticism. I am not talking about crossdressing as a fetish, that’s another subject altogether, I’m referring to wearing clothes that are, well, SEXY.
Of course there is a difference between a sexy dress and a dress that you would wear to Sunday brunch. I mean, that’s one of the reasons I am so enamored by clothes. There’s SO much to wear for literally any occasion. Yes, lingerie is SEXY but I don’t wear lingerie because I am turned on by it. I wear sexy dresses because they make me feel confident and attractive, but they don’t, ah, arouse me.
Am I making sense? I mean, I know what I mean and I hope you do too. 🙂
I want to wear (and I do) what I think is beautiful, cute, and sexy. Little black dresses look amazing on anyone and I love wearing them. I think a cute skirt and boots look very cute so I wear them.
Corsets are sexy so I wear them (I mean, aside from how functional and practical they are). This thinking can also cover what I think is, and would be fun to wear. Whenever the calendar is flipped to October I start to think (and dream) about what Hannah will be for Halloween. There is a seemingly endless list of options and each year I dream about what I am going to dress as. I admit that some of the costumes are almost, well, cliches. Television shows and movies that have costume parties almost always have a girl wearing a schoolgirl outfit. Or a girl wearing lingerie and cat ears. You get the idea. French maids are also pretty common. I had always wanted to wear a French maid outfit. Like lingerie they always seemed so… elaborate. The skirt floofed out with a white petticoat, fishnet stockings, a cute little apron, patent leather stilettos…
Wearing a French maid outfit was on my wish list and I finally accomplished this milestone at my most recent photo shoot. I love looking at these photos and I think I nailed the look I was going for.
But as I mentioned before, my wish list is dwindling and it’s bittersweet crossing things off of the list. Like finishing your reading list. It’s like, well, what do I read (or wear) next? I like setting goals and trying to accomplish them. It all sounds so silly (and probably a little shallow) to think like this. But like my gender identity, this is how I am wired. I was born this way.
It’s a little funny to see clothes in such two completely, almost contradictory, ways. One one hand clothes are pieces of fabric sewn together to cover our skin. On the other hand, clothes are EVERYTHING. Wearing leggings keeps someone warm, but wearing leggings are OMG, comfortable and a way to connect to my femme side, my other gender identity. Panties are not JUST underwear, they are a small and beautiful way for me to stay in touch with my femme self when I am in boy mode. I think society gets waaaaay too worked up when it comes to who wears what. The world (for the most part) loses its mind when a boy wears nail polish. When the world’s collective mind has a meltdown about a boy wearing a skirt I think it’s a huge overreaction to someone wearing a piece of fabric. But at the same time, clothes are MORE than a simple piece of fabric. Clothes can, and do, shape our confidence and our perspective. I wouldn’t be surprised if there was something in your closet or drawers that makes you feel cute, beautiful, or sexy.
A French maid costume (or a skirt or a LBD or whatever) is sewn together with pieces of fabric and is nothing more than that. But on the other side of the coin the clothes can be a milestone. Wearing something you have dreamed about for years is, in a way, an accomplishment. It’s crossing something off your wish list. It’s kind of… well, funny that such a sexy costume can make me feel such a myriad of emotions. I felt cute but also a little… well, bittersweet (goodness I am using this word a lot here but if the stiletto fits…). In some ways the costume, like my lingerie shoot, signified getting near the end of my”to-wear” list.
I’m not quite done yet with my list but if you have some ideas, I would LOVE to hear them, lol.
I am very curious about crossdressing, please let me know where I can shop.
It all depends on what you’re looking for.
Every t-girl/crossdresser is different and we all need and want different things. Thankfully there are quite a few options out there. When it comes to retailers that design for and market to our community, I shop online with En Femme, Xdress, Homme Mystere, Glamour Boutique, and the Breast Form Store the most.
I purged the other day but it’s not what you think.
My closet has been just… overflowing with clothes and heels. Normally it’s a wonderful thing, but it had become out of control. I was essentially out of room.
And yes, I know this is not a bad problem to have. I know I am lucky to have so much clothes. I really, really do understand that.
Picking out something to wear or looking for a specific outfit was becoming unbearable. I couldn’t find anything and being able to look through my wardrobe was next to impossible. Same with my shoes. I have heels that I bought ten years ago that I’ve never worn.
So, it was time to go through everything. I started with dresses and found outfits I’ve never worn before and dresses I forgot I had. Some dresses were met with an “ew, why did I buy that?” and some were “OMG, this is so cute, why don’t I wear this more often?” Although it’s fun to buy new clothes, it’s equally fun to find something you forgot you already had. I sorted everything into two piles, one to keep, the other to put in storage in a hope chest (and now my hope chest is overflowing but that’s a problem for another day). As I went through these dresses I remembered learning the importance of knowing your measurements and that a dress might look cute online but it might be cringe when you get it.
I then moved onto tops and skirts, but I kept all of these. I don’t own a lot of blouses and skirts compared to dresses and there’s a lot of potential to put together a lot of different outfits with a good blouse and a cute skirt, so for practical purposes I held onto all of these.
The heels were next and goodness was I reminded of how much I’ve learned over the last decade or so. I used to buy almost any heel that was my size. It didn’t take long for me to learn that a size 12 doesn’t mean anything, you have to try on shoes (if you can) before you purchase them. I tossed the heels that didn’t fit and the heels that were too scuffed and scratched to wear again. By the time I was done, the shelf in my closet was no longer sagging from the weight.
As I get older I am noticing I want to simplify more. I feel that I have accumulated too much and I own too many things. I am learning to let go of things that I will never use, read, or wear again. Of course, this is easier said than done. Unfortunately what is working directly against this desire to pare down is getting more nostalgic as time passes. While going through my closet I founded dresses that I wore for my first photo shoot, or dresses I was sent to review. There’s a lot of memories associated with outfits like that and I found it hard to decide whether to keep them in my closet or into storage. And yes, putting something into storage isn’t getting rid of it, but it also means that I don’t think I’ll be wearing it anytime soon (or ever again).
It was a lot of work going through my closet, both physical as well as emotional. It’s kind of silly because I know that a dress is just fabric but I think a girl like us has a deeper, more complex relationship with clothes than others. A dress might be just a dress to someone else, but for me, it’s a symbol. It represents something. It might be the first dress I ever bought, or it might be a dress that I had worked up the courage to try on in a store, or a dress I never thought I’d be brave enough to wear. A dress might be a symbol for our femininity. A dress is more than the material it’s made of, it’s so much more to a girl like us.
Today my closet is a lot more manageable and I am excited to wear outfits again that I forgot I owned… and create new memories with them.
Hi Hannah. I’ve taken to dressing up and have been out a few times in low public areas. I don’t want to go down the road of shaving my legs or arms yet.On those days I did go out I wore black stockings.Now with the warmer weather here, what would be best thing to do? I could wear jeans but sometimes it’s too hot for those. I have got a few dresses but would I need to wear something to cover my legs. Would I have to stick to stockings or tights? Also, I’m struggling to get my eyes right, probably due to still having a shaky hand. Any tips?
When it comes to makeup, the only thing you can do to overcome a shaky hand is practice, practice, practice. When I was learning eyeliner my lines were usually shaky and smudgy but the more I did it the more progress I made. Don’t practice right before you go out, practice when you have time to do your makeup, wash it off, and try again. A trick I learned when I was first doing eyeliner was drawing small dots on my eyelid and then connecting the dots to make the line. Makeup tutorials can help, but it all comes down to practice and learning through repetition.
I always, always, always wear stockings or tights when I go out, no matter how hot it is. I wear stockings because they help even out my skin color and well, because I love the way a stocking looks. I tend to wear brighter colors, or floral patterns in the summer so nude stockings and tights tend to look better with what I am wearing compared to black stockings. If you aren’t ready or able to shave your legs you may want to consider wearing two pairs of stockings to help hide your leg hair. But just because it’s summer it doesn’t mean I’ll avoid black stockings. If the dress or occasion pairs better with black, then I’ll go with black, no matter the season. I tend to wear black stockings with skirts for some reason.
And one more thing, you can do what you want, but I never wear non-nude stockings or tights with open toe heels. I think you can get (barely) get away with nude stockings (and fishnets) with open toe heels but anything else looks a little tacky.
If it’s too hot for jeans, have you considered leggings? Leggings are super cute and super femme and can be paired with a cute top, certain dresses, or a casual t-shirt. The versatility of leggings is a-maz-ing.
I have always loved lingerie. It was my first introduction to this beautiful world and today it helps me stay connected to my femme side when I am in boy mode. Growing up I had the occasional chance to try on a bra, nylons, and panties. I was fascinated with and in love with the pairing of stockings and a garter belt and for a long time I had dreamed of wearing such beautiful lingerie. The mannequins at department stores always drew my eye when they modeled such amazing lingerie. When I was in my teens and started to drive I finally had the courage and the ability to purchase a garter belt and it was everything I had dreamed of.
As time passed I started to buy and wear matching bras, panties, and garter belts under my boy clothes. There was, and still is, something so irresistible about matching lingerie. For me, it’s a requirement. As I became more emboldened and braver I started to add corsets and other lingerie to my closet (but would quickly be purged, sadly). Lingerie options always seemed endless and they still are.
When I moved towards actual clothes, it was an entirely new world. Again the choices and the potential were limitless. There’s everything from cute skirts paired with a comfy cardigan to evening gowns. Little black dresses to flirty dresses. Leather, silk, satin, PVC, lace… I wanted to (and do) wear it all. It was an amazing feeling to look for, and add to my wardrobe, new styles, new clothes, new… everything.
It was the same feeling, and the same excitement, when it came to shoes. Stilettos, pumps, thigh-high PVC boots… There’s a thrill knowing that there’s a perfect shoe for any outfit you can think of, and vice-versa.
Oh! And makeup is the same. There are as many looks as there are outfits and occasions. Sultry, vampy, everyday, glam, goth…
I loved the thrill of newness. Wearing something I had always dreamed of. Looking like I always fantasized about. Photo shoots give me an opportunity to wear anything I have always wanted… from lingerie to evening wear, to casual, to fantasy. There is an outfit, a shoe, a look for any feeling or event. Feeling cute? Wear a cute dress. Feeling invincible? Slip into your stilettos. Going to a wedding reception or the mall? You get the idea.
But eventually one might feel that they have done it all. If there’s something I wanted to wear more than likely it’s hanging up in my closet or in a drawer. The newness kind of wears off a little. It’s true that fashion is always changing so there is always going to be a new look, a new style that catches our eyelinered eye so that’s fun, but for me my excitement is turning towards experiences and what I could wear on a new adventure. Now that COVID restrictions are easing (Minnesota’s mask mandate is scheduled to end on July 1st!) I am starting to let myself fantasize about potential experiences. Where can I go? What can I do? What will I wear?
I think of everything I dream of doing, getting ready for a wedding or even a formal event, such as a gala, are at the top of the list. How fun would it be to spend hours at the mall looking for the perfect dress? It could be a prom dress, perhaps a bridesmaid dress, or even a head-turning floor-length ball gown. How glamorous would it be to spend the evening dressed in a breathtaking dress?
Prior to the pandemic I traveled for my job. And I did it a lot. It became something I was used to. But flying pretty? Oh my. It’s like when I first went out en femme to simply get a cup of coffee. Getting a coffee was something I did everyday but it was a new experience doing it in a skirt and heels. I think about flying pretty a lot… what I would wear, where I would go, what I would do. How amazing would that be?
I’m always looking for a new style to wear, and always thinking about a new adventure. What are you dreaming about these days?
I noticed that you are getting very comfortable wearing sleeveless dresses. You look great wearing them, besides that is what the women wear. So you are fitting in very nicely. I am wondering what advice can you give to t-girls on how to be confident wearing sleeveless tops and dresses?
I wasn’t always brave enough to wear dresses with thin straps. I used to think my shoulders and arms were toooooo masculine to wear spaghetti straps. But I started to take my own advice when I saw a really cute dress that I really wanted to wear. The hill that I will die on is there is no such thing as passing. No one has a body that is too tall, too wide, too muscular, too ANYTHING to be femme. I am a tall t-girl but there are cis-girls that are taller than me. Are they too tall to be beautiful? Of course not. Am I too tall to be beautiful? Of course not. Are you too tall to be beautiful? Of course not.
This is all easier said than done, obviously. It’s easy to believe something, it’s easy to say this, but doing something requires something else. For me, it required two things. I needed to stop caring (and wondering) what other people thought (and that included what I myself thought). I also needed a reminder that life is short. When the first weeks of COVID hit life was turned inside out. Things were falling apart, things were changing quickly. Things we took for granted, like going outside of the house, seeing friends, and shopping were all very different and weren’t the safest things to do. I started to think about all the things I still wanted to do and how I didn’t want to live my life with any regrets.
And yes, it’s shallow but I didn’t want to have a life where I didn’t wear a certain outfit that I loved. I found a dress that I loved but it would show off my shoulders in a way that I never did before. I didn’t think I could pull it off. But fueled by the new uncertainty of the world I bought the dress and I promised myself I would wear it out.
And I DID. And I looked amazing. And I know that’s egotistical.
I wish I had let myself wear dresses like this sooner. I wish I didn’t let myself stop myself. Now I have beautiful and fun dresses without sleeves, with halter ties, and thin straps. I also have a confidence that I didn’t think I would.
As for advice all I can say is to wear what you want. Stop caring what others think (because unless you specifically ask someone you won’t know what they think anyway). In terms of practical advice, have a strapless bra and a cover up. When I wore the animal print dress in the picture above I had a long cardigan with it. It was a little chilly that morning and it helped keep me warm, but I also looked at it as armor that I could put back on (or leave on) if I wasn’t quite ready to flaunt what I got.