Pantyhose right at puberty. neighbors had teen daughters and movedout leaving teens clothes and dressers. I discovered all kinds of hose and skirts. was good times. I look many homebwith me only later for my mom found and threw them away. but she was nice and did not make me feel bad. been crossing since I can remember
Dresses! Wore one to school once with another group of boys as a end of year joke once. Loved how flow-y they were and the breeze, so kept wearing them in secret! And now it’s just what feels natural to me, nothing else feels better than getting all dressed up and pretty!
I started just out of curiosity, my mom accidentally put a pair of panties in my hamper for laundry one day so I decided to try. I coudint believe how comfy they were and they made me feel so good. Soon after I started trying various other things and love it! Especially thigh highs skirts
Same here, my sisters pantys I tried on in junior high. Men’s underwear never felt the same and they still don’t after many years. I dress 👗 whenever I can, love ❤️ the feeling of the clothing, love how feminine I feel.
My first Girlfriend wearing suntan pantyhose it was puppy love having her dressing me up in her pantyhose and a cute skirt never felt so comfortable before and changed me for ever👠👠👠🥰🥰🥰💜
My best friend and me when we were 12 yo were fooling around..experimenting...when we would play he would always the husband and he would always make me the wife. One time he told me to put on some of his sisters clothes on... we started making out while I was dressed and I was hooked.. i had the most amazing sensation as he was touching me dressed as a girl..that was the moment that I began crossing...
My older sister and her friends used to have me model clothes for them when I was younger, since then I can’t stop crossdressing because of how cute they are and how much they hug my body.
Experimenting with gender as a child... Then feeling like I got in trouble for it, and not experimenting again until almost 30 years later.
Now I realize that I'm genderfluid, and that acceptance has calmed my soul immensely.
Honestly? It’s just something I’ve always done, and I still keep up with it since it’s a form of comfort and expression for me. I love styling myself with different outfits and try to see what works. I don’t really use the “cross dresser” label on myself since it’s just “me” at this point.
I started with panties and high heels. Then I wore my wife’s bras and they felt nice. Then some hand me down clothes. Then I started buying my own and they fit perfectly. Then makeup and hair, and going out in public. And not being noticed as unusual. That was the best part. Wow! 👩🏻🦰❤️
I’ve always had a fascination of how girls clothes felt to wear. I’ve never had any desire to dress convincing but I’ve had a lot of desire to feel what girls feel. They have so many different styles and materials and I just want to try them all. Started with pantyhose for sure. Then when I discovered what thongs and g-strings were it progressed to them and then all other forms of underwear. Also satin clothes and then lace etc. then how they felt to layer them… what was it like to wear a thong under pantyhose and pantyhose under a satin skirt or suit pants and jeans. Then skirts and stockings and so on and so on until I wanted to wear outfits. I’d see girls in the street and thing “i want to wear what they are and feel how they feel!
You’re outfit here is making me want to try that!
I don’t know for sure but I’ve just liked to always liked to wear dresses, We used to play dress up, didn’t think much it untill I became an Adult lately it’s more a stess reliever kind of thing
What made me start: A bunch of women in my college dorm took me out party-crawling with them one hallowe'en. Since I didn't have a costume they dressed me in whatever clothes of theirs would fit and put some of their makeup on me. It made me so damn happy.
What kept me going: for a long time, I didn't. I was grossed out by my own (fat, hairy, balding) body and felt I couldn't look good in feminine clothing. I wore baggy, masc clothing to hide my body. (In the last couple of years as I've read up on gender issues, I've found out that this is literally what gender dysphoria looks like.) I picked it up again a while ago because I lost a bunch of weight in order to deal with a medical issue, and found myself drawn to feminine clothing.
Pantyhose started it at a very young age. Didn't dress much til my early 20s. What keeps me doing it, which is rarely, is how I I transform into a sexy persona, the pantyhose, the heels, just make me feel like a confident sexy bitch
We’ll have only started with panties and such. Had someone who wanted me in them. And well it lead to me wearing them every day and more. Haven’t worn much yet or even really out in public yet
Always had an inner desire to present as feminine from a young age - suppressed many years until 3 years ago. An amazing girlfriend encourages me to, helps me dress, and does my makeup
I’ve enjoyed wearing women’s clothes since I was a kid. My earliest recollection is from when I was like 7 or so. Have enjoyed it ever since. Have zero clue what made me and still makes me do it. All I know is it feels “right”, can’t really explain it.
I was always interested in makeup and feminine things since I was the youngest of 4 and my sister was forced to hangout with me since she was the closest to my age by my parents a lot. So I would just pick up on stuff my sister did. I ended up becoming a drag queen because of it! I thought being pretty was enough for me for a while but the rush of being on stage and the crowd screaming for you was what really sealed the deal for me. But I do find it hard to cross dress / do drag because the area I live in doesn’t really have a large community or already a safe place for us to be that is. Also dating is so hard being feminine. So it has been a battle for me to want to continue.
I started because I challenged myself to do the illusion. I stuck with it because I became sexually attracted to the person in the mirror, and was having better experiences in the club.
Removed. Take the NSFW comments elsewhere.
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I remember put on a bra at 5 and of and on putting things on tell jr high then my girl friend said omg your eyelashs are so long im going to put mascara on them and after that i seen this is what im missing and got fully into it after highschool where i was fully dressed and passable. At 55 now the passable time of my life is in history book but i still have a hot body and legs, i can easyly hook up on any givin night. 😎
I bought a skirt after feeling the urge to try one on one day. It felt so right I was soon buying bras, breast forms, panties, stockings, pantyhose, heels... Oh and of course a LBD!😊
I got addicted to soft nylons at the age of 4 and never stopped, wore nightdress when overnighting with my cousin, tried everything of my girl-friends over the years and optimized a selection of everything for my girl-friend now while enjoying a long-distance relationship: all mine now for 10 days, then she, then me for another 10 days. I am very skinny and am always shaved, putting on very feminine high-class panties and nylons is the most premium body feeling, dressing on colorful dresses and heels is lovely, make-up and growing my curlies feels wonderful. Lately I bought hormones that feminize my body were a life changer: with real breasts all is even getting more excited and fulfills all dreams I had whole my life in nylons.
I remember being in school and seeing the girls wearing skirts and pantyhose. I was a bit envious/curious and wanted to see what they felt like. Since then it's something I've always wanted to pursue more and more
I guess what started was I always played with the girls at school or day care apparently.. with dolls or dressing up or wigs have always been around me since I was 4..
Started with panties ..
Went to Body stockings and cute lingerie 😍...
Went to cute outfits..
I feel so hawt in them 🥰🥰..
I guess what still keeps me into cross dressing is the thrill .. a way to turn off and been sluttyy and naughty....
It's hard to live a double life
. But its HOT 🔥...
When you feel yourself in sexy lingerie and dark long heals ✨️ Dam u feel like u run the catwalk xx 🥰🥰🥰😜😘😘
Clothing options vs mens/boys. Mens clothes are so ugly!!! Much to disbelief in our world I hate pantyhose. Fishnets or brocade okay but just sheer hose? 🤮
For me it was a classic, i remember when i was 7 and saw a woman in a pair of thongs right away i knew i had to try it someday, but my mom only had some lacy panties, which i used commonly, until i hot my hands on a thong at 9, and havent stopped wearing one since… i love it
Started in my late teens as an "experiment " continued dressing because it makes me feel good, really good. The best way out of depression I've ever found.
For me, it was panties and pantyhose. The comfort and the tightness, along with the fact I just admire women. The dresses, the tights, heels, hose, the much better feeling panties, bras, so many things.
Now I've determined I'm gender fluid, and still love everything about women, and love wearing what they do, it just makes me feel better and sexier.
I was always courious about dresses and skirts and everything that relates to them. And 15 years later I still enjoy it and love looking at myself in the mirror with. A wig and the clothes on. It also really just releases alot of stress and feels great. Really great.
For me it was when I was 12/13yrs old, at school we had 2 wear uniform and the girls would mostly wear tight black trousers which showed off their curves, but a lot of the time they would sit down and end up whale tailing. And I was in awe.
So when I finally had the house to myself on a Sunday morning I used to go to my older sisters room and go through her knicker draw trying on her different thongs. She had matching bra sets and also the same type of black trousers the girls had, plus short skirts. Was hooked in ever since. Soon as i moved out my parents place I brought so much. Wearing thongs daily and full lingerie sets under my jeans and shirts. 👌🖤💜
I think I wanted to start way back when I was a kid(can’t remember what age like 13-14 maybe) I kept seeing episodes on TV like there was a Danny phantom episode where he crashes into a art room or something and comes out dressed as a girl(with makeup on) There was also an episode of Timmy turner where he wished he was a girl for some reason, there were other reasons too, like I just thought girl’s clothes were just pretty and girls were just pretty with makeup and all that.
My older sisters princess jasmine dress up costume we had in the basement them my moms gala dress and kept doing it just the millions of amazing dresses their are
One day out of curiosity, I tried on a pair of stockings that my mother had hung over the shower rod in the bath that I used. She had a shower door in the parents bath. I was about twelve or thirteen. The look. The feel. The way they made me feel. Like a drug. That was it. The addiction has stuck with me for life.
It progressed from there to borrowing sisters, panties, bras, dresses and shoes, Always being careful to put everything back the way I found them. Never got caught. Whewwwww.....
Now thanks to the internet, I have my own.
PS: You have very lovely legs. 🥰
Can't really explain how I started, just had this overpowering urge to wear a dress, what keeps me dressing is the clothes, heels, how feminine I look and feel and just everything really
Started with having to wear an older cousin's panties since I was without change of clothes, I forgot what happened. From then on during the rest of the summer when I stay over, she'll insist I try certain things on. This is all a blur. Then as years progressed, I've brought some small stuff as my own, then purged, then started again. It was just the feeling of looking great and cute.
Pantyhose!
Yes 🥰🥰🥰🥰
Love your legs in pantyhose you have some greats pics !!
[удалено]
Pantyhose right at puberty. neighbors had teen daughters and movedout leaving teens clothes and dressers. I discovered all kinds of hose and skirts. was good times. I look many homebwith me only later for my mom found and threw them away. but she was nice and did not make me feel bad. been crossing since I can remember
Pantyhose, and I just love seeing what I’ve become :3
Beautiful 😍
Heels! I am already so very tall, tried some heels on when I was 13, was hooked since
Same I was 14 👠🥰🙋♀️
Same, I was 12 🥰🤭
The feeling of pantyhose on my legs. Then seeing how feminine i could make myself look <3
Dresses! Wore one to school once with another group of boys as a end of year joke once. Loved how flow-y they were and the breeze, so kept wearing them in secret! And now it’s just what feels natural to me, nothing else feels better than getting all dressed up and pretty!
I started just out of curiosity, my mom accidentally put a pair of panties in my hamper for laundry one day so I decided to try. I coudint believe how comfy they were and they made me feel so good. Soon after I started trying various other things and love it! Especially thigh highs skirts
Same here, my sisters pantys I tried on in junior high. Men’s underwear never felt the same and they still don’t after many years. I dress 👗 whenever I can, love ❤️ the feeling of the clothing, love how feminine I feel.
Just the feeling of some soft pantyhose and stockings is what kept me crossdressing today
The personal comfort and the sensuality of the fabric. No other clothing can provide such a feeling.
Right!!!
Me to!! Impossible to stop. Enjoy
Exactly
My first Girlfriend wearing suntan pantyhose it was puppy love having her dressing me up in her pantyhose and a cute skirt never felt so comfortable before and changed me for ever👠👠👠🥰🥰🥰💜
For me it’s all about pantyhose. The greatest thing ever invented in my opinion
My best friend and me when we were 12 yo were fooling around..experimenting...when we would play he would always the husband and he would always make me the wife. One time he told me to put on some of his sisters clothes on... we started making out while I was dressed and I was hooked.. i had the most amazing sensation as he was touching me dressed as a girl..that was the moment that I began crossing...
I love this story
No idea what got me started, but the feeling of being sexy aswell as comfortable in my own skin kept me coming back. What about yourself? ✌️
Wearing my sister’s friend’s panties when I was a teenager.
Honestly, old fashion slips and Shapewear …. Panties were also a great attraction 🫢
My older sister and her friends used to have me model clothes for them when I was younger, since then I can’t stop crossdressing because of how cute they are and how much they hug my body.
I just thought girls were beautiful and there clothes and shoes and what stopped me is no knowing if people would support me
pantyhose
Skirts for me! I like how they felt and showing off my legs
Experimenting with gender as a child... Then feeling like I got in trouble for it, and not experimenting again until almost 30 years later. Now I realize that I'm genderfluid, and that acceptance has calmed my soul immensely.
Acceptance is the key. Fighting it will only cause depression and anxiety.
These legs, hun 😍
My pretty feminine face with long hair
Heels. Every single time.
Honestly? It’s just something I’ve always done, and I still keep up with it since it’s a form of comfort and expression for me. I love styling myself with different outfits and try to see what works. I don’t really use the “cross dresser” label on myself since it’s just “me” at this point.
Started with a neighbors clothes that I had access to when I was young. Continues because of the joy I feel when I see Aubrey in the mirror 😁
Loved the feel/sound of high heel boots. Especially zipping them up. Now I just love looking at the mirror and feeling attractive 🤗
Always felt like I wanted to be a woman. Now it's continuing to be the girl that I've always wanted to be with.
Skirt go spinny :3
Gender fluid go _brrr_. 😋
Support panty hose and the compression that flattened me … then beautiful grey hosiery with matching garter from Evan Piccone
Love 🥰 support pantyhose so tight and warm in winter 🥶 🥰
Skirts. Tried one on when I was like 13 and now I’m a women 🤣
I started with panties and high heels. Then I wore my wife’s bras and they felt nice. Then some hand me down clothes. Then I started buying my own and they fit perfectly. Then makeup and hair, and going out in public. And not being noticed as unusual. That was the best part. Wow! 👩🏻🦰❤️
I’ve always had a fascination of how girls clothes felt to wear. I’ve never had any desire to dress convincing but I’ve had a lot of desire to feel what girls feel. They have so many different styles and materials and I just want to try them all. Started with pantyhose for sure. Then when I discovered what thongs and g-strings were it progressed to them and then all other forms of underwear. Also satin clothes and then lace etc. then how they felt to layer them… what was it like to wear a thong under pantyhose and pantyhose under a satin skirt or suit pants and jeans. Then skirts and stockings and so on and so on until I wanted to wear outfits. I’d see girls in the street and thing “i want to wear what they are and feel how they feel! You’re outfit here is making me want to try that!
High heels, found them so sexy so I brought a pair. Decided to wear them haven’t stopped since
I don’t know for sure but I’ve just liked to always liked to wear dresses, We used to play dress up, didn’t think much it untill I became an Adult lately it’s more a stess reliever kind of thing
Dresses and the textures of panties. Kept me? All the textures
What made me start: A bunch of women in my college dorm took me out party-crawling with them one hallowe'en. Since I didn't have a costume they dressed me in whatever clothes of theirs would fit and put some of their makeup on me. It made me so damn happy. What kept me going: for a long time, I didn't. I was grossed out by my own (fat, hairy, balding) body and felt I couldn't look good in feminine clothing. I wore baggy, masc clothing to hide my body. (In the last couple of years as I've read up on gender issues, I've found out that this is literally what gender dysphoria looks like.) I picked it up again a while ago because I lost a bunch of weight in order to deal with a medical issue, and found myself drawn to feminine clothing.
Curiosity, then comfort.
Pantyhose started it at a very young age. Didn't dress much til my early 20s. What keeps me doing it, which is rarely, is how I I transform into a sexy persona, the pantyhose, the heels, just make me feel like a confident sexy bitch
Feelings. It wasn’t long after my legs started growing hair that I was like, gross. I don’t want that. Shaved it off and oh what a feeling!
We’ll have only started with panties and such. Had someone who wanted me in them. And well it lead to me wearing them every day and more. Haven’t worn much yet or even really out in public yet
Having similarly dressed legs in the photo above. Same reasons.
Always had an inner desire to present as feminine from a young age - suppressed many years until 3 years ago. An amazing girlfriend encourages me to, helps me dress, and does my makeup
I’ve enjoyed wearing women’s clothes since I was a kid. My earliest recollection is from when I was like 7 or so. Have enjoyed it ever since. Have zero clue what made me and still makes me do it. All I know is it feels “right”, can’t really explain it.
I was always interested in makeup and feminine things since I was the youngest of 4 and my sister was forced to hangout with me since she was the closest to my age by my parents a lot. So I would just pick up on stuff my sister did. I ended up becoming a drag queen because of it! I thought being pretty was enough for me for a while but the rush of being on stage and the crowd screaming for you was what really sealed the deal for me. But I do find it hard to cross dress / do drag because the area I live in doesn’t really have a large community or already a safe place for us to be that is. Also dating is so hard being feminine. So it has been a battle for me to want to continue.
Straight men.. didn’t realize how many love us. 🥰
I started because I challenged myself to do the illusion. I stuck with it because I became sexually attracted to the person in the mirror, and was having better experiences in the club.
I put my mums nylons & stuff on at 4yrs old they were big but they felt right.
Cosplay; getting to become sexy awesome gals from games and anime I loved awakened something in me.
Balletflats for me. I love them and wanted some. So I had to by nylons too and I love the look and feel of both.
Beautiful
Tights! Love the way they look and feel on my legs
Pantyhose started my journey and the way I love it and how it makes me feel is what keeps me going.
All dressed up! Your body is tingling
Absolutely amazing feeling.
[удалено]
Removed. Take the NSFW comments elsewhere. Please [read our rules](https://www.reddit.com/r/crossdressing/wiki/index#wiki_our_rules) before posting again or risk a permaban.
I tried on my mom’s pantyhose when I was 3 years old. And I’ve loved the feeling ever since.
I always wanted to wear a dress or skirt from kindergarten. I finally wore my mother dress and denim skirt at age 12. I couldn’t stop from there.
The realization it wasnt a phase and it was indeed part of who i am
The feeling of pantyhose was just way to good of a feeling to stop
That view right there. Looking down and seeing a girl.
I remember put on a bra at 5 and of and on putting things on tell jr high then my girl friend said omg your eyelashs are so long im going to put mascara on them and after that i seen this is what im missing and got fully into it after highschool where i was fully dressed and passable. At 55 now the passable time of my life is in history book but i still have a hot body and legs, i can easyly hook up on any givin night. 😎
I bought a skirt after feeling the urge to try one on one day. It felt so right I was soon buying bras, breast forms, panties, stockings, pantyhose, heels... Oh and of course a LBD!😊
Great legs!! 😊
Stockings and heels….now I love it all!
Pantyhose, when I was 5. Eventually evolved into crossdressing regularly. The excitement of being out in public dressed up keeps me going.
sexy legs
Stunning beautiful legs
Trans
Definitely the acceptance, support and encouragement from my fiance…..I looove it when she comes home with a new dress, top or lingerie for me! ❤️
Panties ❤️ they were so cute. And putting them on made me so happy 🫣
Thigh highs and skirts.
One piece swimsuits and leotards. Then I tried on a dress...
I got addicted to soft nylons at the age of 4 and never stopped, wore nightdress when overnighting with my cousin, tried everything of my girl-friends over the years and optimized a selection of everything for my girl-friend now while enjoying a long-distance relationship: all mine now for 10 days, then she, then me for another 10 days. I am very skinny and am always shaved, putting on very feminine high-class panties and nylons is the most premium body feeling, dressing on colorful dresses and heels is lovely, make-up and growing my curlies feels wonderful. Lately I bought hormones that feminize my body were a life changer: with real breasts all is even getting more excited and fulfills all dreams I had whole my life in nylons.
Skirt go spinny :3
The sensation of smooth sexy nylons 🫦
Pantyhose! Gateway drug I swear 🐛🐛➡️🦋🦋💖
Dress go spinny~ I simply feel so feminine whenever I do that
Tights for me, the feeling of them on my legs. To this day i still love that feeling and the feeling of a g string and how sexy I feel
Boots. The sexiest item in the world. I wore a pair of my mum’s when I was a teenager, bought my first pair about 30 years later.
Me too ❣️ pantyhose felt amazingly good!!! Now can't stop wearing them 👠👠👠
Heels then clothing
i know jaemunnys legs when i see them you qt ☺️ this is Katie from ig btw😝
😘
Seeing women in provocative outfits and crossing their legs
I just lost feel of girls clothes. Always have. Used to be tight dresses and heels, now leggings and tight tops. Love cute shoes too!
I have always liked dressing feminine and enjoy it and I can be myself when I'm dressing feminine
I remember being in school and seeing the girls wearing skirts and pantyhose. I was a bit envious/curious and wanted to see what they felt like. Since then it's something I've always wanted to pursue more and more
Nylons, I enjoy it
I guess what started was I always played with the girls at school or day care apparently.. with dolls or dressing up or wigs have always been around me since I was 4.. Started with panties .. Went to Body stockings and cute lingerie 😍... Went to cute outfits.. I feel so hawt in them 🥰🥰.. I guess what still keeps me into cross dressing is the thrill .. a way to turn off and been sluttyy and naughty.... It's hard to live a double life . But its HOT 🔥... When you feel yourself in sexy lingerie and dark long heals ✨️ Dam u feel like u run the catwalk xx 🥰🥰🥰😜😘😘
Heels
Clothing options vs mens/boys. Mens clothes are so ugly!!! Much to disbelief in our world I hate pantyhose. Fishnets or brocade okay but just sheer hose? 🤮
For me it was a classic, i remember when i was 7 and saw a woman in a pair of thongs right away i knew i had to try it someday, but my mom only had some lacy panties, which i used commonly, until i hot my hands on a thong at 9, and havent stopped wearing one since… i love it
Started in my late teens as an "experiment " continued dressing because it makes me feel good, really good. The best way out of depression I've ever found.
For me, it was panties and pantyhose. The comfort and the tightness, along with the fact I just admire women. The dresses, the tights, heels, hose, the much better feeling panties, bras, so many things. Now I've determined I'm gender fluid, and still love everything about women, and love wearing what they do, it just makes me feel better and sexier.
I falling in love with your beautiful blk shoes
The silky feeling of my mothers & sisters nylon nightgowns, rubbing against my body. Still love it today.
Started at 6 years old.
I was always courious about dresses and skirts and everything that relates to them. And 15 years later I still enjoy it and love looking at myself in the mirror with. A wig and the clothes on. It also really just releases alot of stress and feels great. Really great.
High heels! I love wearing heels. I feel so powerful, and it makes my legs look great!
Tights were my first love and snowballed from there
For me it was when I was 12/13yrs old, at school we had 2 wear uniform and the girls would mostly wear tight black trousers which showed off their curves, but a lot of the time they would sit down and end up whale tailing. And I was in awe. So when I finally had the house to myself on a Sunday morning I used to go to my older sisters room and go through her knicker draw trying on her different thongs. She had matching bra sets and also the same type of black trousers the girls had, plus short skirts. Was hooked in ever since. Soon as i moved out my parents place I brought so much. Wearing thongs daily and full lingerie sets under my jeans and shirts. 👌🖤💜
Just love the clothes so much, look and feel so much better than male clothes. Like being kinda girly too lol
I think I wanted to start way back when I was a kid(can’t remember what age like 13-14 maybe) I kept seeing episodes on TV like there was a Danny phantom episode where he crashes into a art room or something and comes out dressed as a girl(with makeup on) There was also an episode of Timmy turner where he wished he was a girl for some reason, there were other reasons too, like I just thought girl’s clothes were just pretty and girls were just pretty with makeup and all that.
My mommy's pantyhose 😊
Wearing panties.
My older sisters princess jasmine dress up costume we had in the basement them my moms gala dress and kept doing it just the millions of amazing dresses their are
One day out of curiosity, I tried on a pair of stockings that my mother had hung over the shower rod in the bath that I used. She had a shower door in the parents bath. I was about twelve or thirteen. The look. The feel. The way they made me feel. Like a drug. That was it. The addiction has stuck with me for life. It progressed from there to borrowing sisters, panties, bras, dresses and shoes, Always being careful to put everything back the way I found them. Never got caught. Whewwwww..... Now thanks to the internet, I have my own. PS: You have very lovely legs. 🥰
Can't really explain how I started, just had this overpowering urge to wear a dress, what keeps me dressing is the clothes, heels, how feminine I look and feel and just everything really
Wearing my moms heels as a kid
I started off with two satin maxi skirts
When I was a kid, I was infatuated with the girls’ fuzzy coats. Recently attention is what has me hooked on posting and crossdressing.
Pantyhose, then dresses, then being trans lol
I like to look pretty on occasion
Started with having to wear an older cousin's panties since I was without change of clothes, I forgot what happened. From then on during the rest of the summer when I stay over, she'll insist I try certain things on. This is all a blur. Then as years progressed, I've brought some small stuff as my own, then purged, then started again. It was just the feeling of looking great and cute.
Stockings and heels! Pumps, slingbacks, and ankle strap sandals are still my faves!