Drab date in heels

[heatherdress]

I have had the urge to modify my male clothing and appearance - and let my feminine side move in. Today, I wore a pair of 3 inch heeled boots with jeans. It was my wife's suggestion. She knows how much I enjoy dressing and she also likes the edgy additions. It was great. No stares, no comments - felt normal. I wore longer jeans and the boots were not stiletto heels. Mall, movies, Walmat, Petsmart, restaurant. It was fun and I felt great. I have some longer length jeans and pants - several are womens jeans - fit and feel great. Seems crazy - but it was even more fun that being fully dressed. My wife bought me a new pair of Nine West black laced 4 inch heels and boots today for future dates and encouraged me to continue and be even more daring. Drab is becoming drab plus.

[Beverley Sims]

Heather,
I advocate getting dressed properly, a half and half androgynous look can be risky in some surroundings.
You can invite ridicule, that is my gravest fear.

[Rita C.]

Girl you go for it, I do the same thing. my heels are 2 in. but I might wear boots one day or pumps the next day.

[Princess29]

Anyone can find something to ridicule you over, regardless of how you are dressed. If you are tall, short, fat, thin, big hands or small hands, they will find something to pick on

[deebra]

Heather everything you wrote applies to me. I'm about ready to walk out the door and run errands, dressed in my 3" boots, bootcut girl jeans, orange nylon tee and black string panty with matching bra and forms. It's such a different and wonderful feeling walking and moving in girl clothes. They are such a turn on and where guy clothes offer nothing wearing form fitting girl clothes just feels so feminine and sexy and good and right. Truly love walking in heels and the weight and sway of my D boobs.

[MascStilettoBoy]

I think you know how I feel on the topic ;-)

I am all for mixing and the androgynous look... ESPECIALLY when it comes to heels! Glad you enjoyed!

[Sarasometimes]

Glad to hear you can mix the two to your taste. Having a supportive woman on your arm probably makes it much easier and less noticable to others. Enjoy those new heels and any pics available?

[I Am Paula]

Before something can be accepted, somebody has to push the boundries.
Remember, at one point Ziggy Stardust was shocking.

[Rhonda Jean]

I sometimes wear heels in male mode, too. I think it's funny, though, that you're talking about going out drab in heels and then you list several things that most would not consider drab. I've done the same thing, and been called out on it. Funny that what we see as drab is quite different from what most people would consider drab! For me, the line seems to be boobs and obvious makeup. Without those, anything else qualifies as drab.

[Rachael Leigh]

Heather I just came back from being out en drab wearing my cute ankle boots, it felt great and that sound you make on the pavement and in the store is just a wonderful sound

[heatherdress]

Thanks for all comments and ideas. All appreciated very much. I still have to learn how to overcome my own inhibitions and fears if I want to do things I dream about doing. What prevents me from fully enjoying, trying, experimenting - is usually me.

[LaraPeterson]

I've been at this for a long time but I've never even considered "mixing" looks until I read this post. I guess it all just went right over my head. Drab plus, what a wonderful description.

[Rachael Leigh]

Lara like I said now that I've done it a couple of times it's a great feeling, especially hearing my heels clicking.
I figure who cares what kind of shoes I'm wearing, besides here in Texas lots of guys wearing boots just not as cute as mine lol

[heatherdress]

Thanks Laura, thanks Leigh. By the way, there are so many female shoe styles which can blend easily and compliment male clothing. I love my heels and now have shoes and boots which I feel very comfortable wearing but also offer some excitement and pleasure and fun. I have discovered that most people don't pay much attention, many don't care what shoes I wear, some may think I am wearing Western influenced footwear with higher heels, and some may observe that I am wearing female shoes or boots with higher heels - so what? I really enjoy wearing Heather's shoes much more frequently.

[SallySC]

I love this thread...as I have mentioned I am new to this wonderful site. I don't think I could ever pass so I pretty much dress in "drab plus" like you mentioned whenever I go out. I do wear my nails with french manicure and recently have added ankle boots with about 3 inch heels and some skinny girl jeans ...I also wear clear lip gloss and a just tiny bit of mascara sometimes. I really haven't had any outrageous looks or comments. It makes me feel so feminine...so much fun!

[heatherdress]

Great Sally. Sounds awesome. I can appreciate how you must feel. It is great that you feel feminine, and you are having fun. You can't spend your life worrying about passing and missing out on opportunities to be you.

[heatherdress]

These are shoes added to Heather's wardrobe by sales over the holidays which will try to make my drab wardrobe less drab. All are very comfortable. I do have pants which are 2 inches longer than I usually wear - and even the brown 3 inch heels are concealed when standing. Maybe I will also try some round toe pumps and heeled boots.

[Algoma]

Love the current women boot styles the block heels blend right in while in drab. Nothing better than going out in womens boot cut jeans concealing 3" heels. Nobody has ever said anything.

[Diane Smith]

I frequently wear heeled shoes and boots when otherwise in drab, same as you, Heather. In fact, I basically have a whole second wardrobe of slightly thicker and less obviously feminine heels that I don't wear with my skirts and stockings. As with many other things, most people don't react, and most of the responses, when they come, are positive.

With ice covering everything outside right now, though, it'll be serious winter hiking boots for the next few days, I'm afraid!

- Diane

[PatChick]

Wow Heather, I really like those brown ones in that top picture! I never thought about doing this until now. They look very comfortable and manageable, but I doubt they have anything that cute in a 12 or 13. Did you get them online or in a store?

[Tracii G]

Heather you are closing in on doing what I call the 50/50 mode.
I wear boots with heels and jeans a lot and I have never had anyone say anything bad only "hey I love your boots."Mostly women say that but there have been plenty of guys say those are cool boots.
I was browsing my local Guitar Center where 90% of the guys and girls that work there know me as a regular.
Had my black 3 in heel boots on and the girl at the welcome station said hi like always we chatted for 30 seconds or so and she looked down and said cute boots how far do the come up?
I showed her and she said I love those they look cool.
Back in the guitar section on of the sales guys said hey cool boots bro'.No tranny police or screams of hey this dude is wearing girls boots ha ha ha.People have moved on and what it really boils down to is that you have the right to wear what you want.

[heatherdress]

Wow Heather, I really like those brown ones in that top picture! I never thought about doing this until now. They look very comfortable and manageable, but I doubt they have anything that cute in a 12 or 13. Did you get them online or in a store?
Thanks a lot Pat. I got them on-line. They have up to size 12 in Clark brand. On sale on their web site. You can also find discount coupons to use on their site on-line for further discount. Amazon and 6PM carries them as well as other similar brands, up to 12 and 13. Tanks again.


Love the current women boot styles the block heels blend right in while in drab. Nothing better than going out in womens boot cut jeans concealing 3" heels. Nobody has ever said anything.

I feel the same way, Algoma. I am really thrilled about wearing my 3 inch heels and boots. It's such a good feeling.

I am going to do the same thing, Diane. Great idea. Thanks.


Heather you are closing in on doing what I call the 50/50 mode.
I wear boots with heels and jeans a lot and I have never had anyone say anything bad only "hey I love your boots."Mostly women say that but there have been plenty of guys say those are cool boots.
I was browsing my local Guitar Center where 90% of the guys and girls that work there know me as a regular.
Had my black 3 in heel boots on and the girl at the welcome station said hi like always we chatted for 30 seconds or so and she looked down and said cute boots how far do the come up?
I showed her and she said I love those they look cool.
Back in the guitar section on of the sales guys said hey cool boots bro'.No tranny police or screams of hey this dude is wearing girls boots ha ha ha.People have moved on and what it really boils down to is that you have the right to wear what you want.

Tracii - I love the idea of your 50/50 mode. I have been wearing my 2 and 3 inch heels and no one even seems to notice - in Walmart, Kohls, Nine West, PetSmart, mall, movies, food stores. It's great. It is almost as much fun as being fully dressed. Maybe even a bit more daring. Do you wear anything else in addition to your heels?

[Nadine Spirit]

I absolutely love blending my male and female sides. I frequently wear clothes of both genders. As well as doing a plethera of other things, lime painting my fingernails in every possible color. I have not tried wearing my female shoes while in male mode, but what a great idea, thanks.

I find it funny that others think that by doing this I am presenting androgynously, without the wig, the boobs, the full makeup, the whole kit and kaboodle, no one ever is confused about my gender or even seems to be aware that I am wearing women's clothes. Of course the finger nails seem to throw them a bit, but no one has ever mentioned the clothes or ever referenced me as androgynous in real life.

[deebra]

Hate to rain on all the good things said but I did what I said in thread 5 and what Ronda said in #9 rang true. It was around 8:50 am, I decided to park my car and walk up to a store to enjoy the walk in fem and check myself out in the reflection in the store window. Well here comes a guy in a car and it was very clear I was a kookie looking crossdresser, to add insult to injury as I was trying to hurry to get back to my car a woman parked next to mine, got out and headed for the store, we met head on. I was very embarassed and ashamed. When I looked at the reflection of myself in the store window it was not as female as my mirrow at home before I went out. The D forms didn't help either. Felt like a damn fool. Now, crazy as it seems this morning I did put the same boots on and longer girl jeans and went in a thrift shop, tried on and bought two pair of girl jeans. Don't think I was outed but walked gingerly in the store to keep the heel noise down, but being underdressed and wearing the boots and girl jeans felt just great. If that damn pink fog hadn't got a holt of me none of this would have happened. Right now I'm just unsure what to wear out and how far I can take this but dressing as a girl and going out really feels good, all opinions are appreciated.

[deebra]

Heather I would like to hear from your wife and her thinking, you said she encourages you and wants you to become more daring, couldn't you being outed bring embarrassment to both of you. How far will you and her take it. However you both must enjoy shopping for girl things and her husband is starting to become her girl friend, of course as a CD I applaude her for this attitude.

[SilkeeLegs]

Heather.......Good for you! I too enjoy wearing a pair of female jeans and a female top and 3 to 4 inch heeld boots as part of my "male" wardrobe. It adds a bit of fun to my otherwise dull male clothes...and no one seems to stare or notice. Keep doing it and let me know how its going

[heatherdress]

Heather I would like to hear from your wife and her thinking, you said she encourages you and wants you to become more daring, couldn't you being outed bring embarrassment to both of you. How far will you and her take it. However you both must enjoy shopping for girl things and her husband is starting to become her girl friend, of course as a CD I applaude her for this attitude.

Deebra - My wife supports me and encourages me to "be me" and to do the things that I want to do. She certainly cares about being safe and relationships with neighbors and appearances for work. But she feels I should try doing the things that I dream about doing. We consider risks and are careful. She does, however, want us both to live life to the fullest and not have regrets that we did not do things that we wanted to do. She doesn't really care what other most people think. She has helped me step out of my conservative boundaries and enjoys new experiences together. She loves me as a man, but also really likes that she has a partner who has a feminine side. She enjoys when I dress as a female. She sees me as beautiful with makeup and a dress and 5 inch heels.

How far will we take it is is not a goal or limit we have set. We try to enjoy what we do for our todays and plan to do new things for our tomorrows. She likes the challenge of expanding my drab attire with some heels and boots. Maybe I will try more. She likes when we go out together when I dress as a female. We have fun. We both feel that my crossdressing is something intimate between us which has enhanced our relationship. I am fortunate.

[Nikki_C]

It is great to hear others walk on high heel in the male mode!
I love the look and feel of heels too!
Several months ago, I did manage to get up the guts to fly in male mode but with longer flare jeans and 6" wedge heels.
It feels so nice!

[heatherdress]

Nikki - I am glad to hear of your experience flying. I know what you mean. The thought of wearing heels dressed as a guy and was really attractive but I was simply afraid to try. I am fortunate that I was urged to go for it. Seems simple but it was very threatening. I was scared that someone might notice - that everyone might notice. I had butterflies getting out of my car and walking into a crowded Petsmart. I thought everyone was watching me - a guy in jeans who was wearing women's heeled booties. I walked in, walked around the store, had some associates ask if I needed help picked up dog food, waited in line between 3 or 4 women who were wearing similar boots - an no one seemed to notice. No one really cared. I felt great. Same in Walmart. I felt more confident and even began to hope that someone might notice and comment. At Nine West, I enjoyed looking at myself in the mirror. I am convinced that I will continue to wear my feminine shoes and heels discretely in male attire and not so discretely when dressed in female mode. It does feel so nice.

[Tracii G]

Heather my everyday look is girls jeans, shoes, t shirts or more femme cut tops.
My hair is past my shoulders and I do use hot rollers sometime to give it some loose curls.
Some times I'll wear one of my wigs and very light make up.You can still tell I'm a guy and that is 50/50 mode.
Had boobs on in this pic but don't always have boobs you get the picture.

[SabrinaEmily]

So you're saying that you weren't mocked by everyone you met? Or alerted to how you're setting all trans people back 100 years by not trying to present as female?

Huh. Fascinating.

[heatherdress]

Thanks Tracii. I love your look. Long hair (which is very common for men today) and a cute outfit that would fit male or female. Of course the breasts are apparent, but I do like your 50/50 style. Your very light make up is not visible which sort of confirms that it is very light. Thanks for sharing some great ideas. I think your style is awesome.


So you're saying that you weren't mocked by everyone you met? Or alerted to how you're setting all trans people back 100 years by not trying to present as female?

Huh. Fascinating.

Sabrina - No one mocked me and I think that maybe I set the trans cause back by only 20 years by wearing a pair of Clark boots with my male jeans. I didn't know the rules said that we had to always try to present as a female.

Sorry if you are offended by someone who discretely wears a pair of women's boots. Thanks for letting me know that I set all trans people (including myself) back 100 years because I did not try to present fully as a female. I am fascinated to learn that there is a scale - 100 negative years for walking around enjoying myself in female shoes. Hmmmm. What would I have set the trans cause back by instead trying to present as a full female and if people mocked me because they could tell I was really a male or because they thought I was ugly or dressed ugly?

I think a lot of people do not or cannot dress in full female attire without harming the trans cause. Do people on this site who only wear panties or bras set the cause back? How about people who wear a female bracelet or a pair of female earrings in drab? Nail polish? What if we are obviously very tall and cannot pass? Or too muscular? What if we can't wear makeup? I just don't think we all can look and dress like Kim Kardashian - and many don't try to - and we still don't set the cause back 100 years as you suggest.

Sorry that I don't agree with you. I think the "trans people", including myself, would be further advanced if we confidently express ourselves in attire we feel to be appropriate for where we happen to be and not worry so much about what other people think.

[Daphne Renee]

I think its great that you are enjoying yourself. Its gets repeated so often be who you are. Dont worry about what others think. Glad to hear your doing just that.

[Majella St Gerard]

I mix and match all the time and even when I do dress all the way, I don't wear a wig or try to present myself as a woman. That's me and that's my style, I like it, my wife likes it and I get a lot of positive feed back from people know and even from people I just meet. I always have something femme on that is noticeable, my nails are always painted and I usually have on a little eye make up. I didn't know there were rules on how to dress, I didn't get a copy.

[SabrinaEmily]

Thanks Tracii. I love your look. Long hair (which is very common for men today) and a cute outfit that would fit male or female. Of course the breasts are apparent, but I do like your 50/50 style. Your very light make up is not visible which sort of confirms that it is very light. Thanks for sharing some great ideas. I think your style is awesome.



Sabrina - No one mocked me and I think that maybe I set the trans cause back by only 20 years by wearing a pair of Clark boots with my male jeans. I didn't know the rules said that we had to always try to present as a female.

Sorry if you are offended by someone who discretely wears a pair of women's boots. Thanks for letting me know that I set all trans people (including myself) back 100 years because I did not try to present fully as a female. I am fascinated to learn that there is a scale - 100 negative years for walking around enjoying myself in female shoes. Hmmmm. What would I have set the trans cause back by instead trying to present as a full female and if people mocked me because they could tell I was really a male or because they thought I was ugly or dressed ugly?

I think a lot of people do not or cannot dress in full female attire without harming the trans cause. Do people on this site who only wear panties or bras set the cause back? How about people who wear a female bracelet or a pair of female earrings in drab? Nail polish? What if we are obviously very tall and cannot pass? Or too muscular? What if we can't wear makeup? I just don't think we all can look and dress like Kim Kardashian - and many don't try to - and we still don't set the cause back 100 years as you suggest.

Sorry that I don't agree with you. I think the "trans people", including myself, would be further advanced if we confidently express ourselves in attire we feel to be appropriate for where we happen to be and not worry so much about what other people think.

Whoa, hold on! I was being sarcastic, and apparently it didn't come across. Sorry for the confusion.

In fact, I think it's complete nonsense to insist that everyone should be, as some members say, "fully dressed" if they're wearing any visible articles of women's clothing. I'm all for everyone presenting how they'd like to, within decency. Also, I'm not surprised no one mocked you -- usually no one does.

I also don't believe anyone gets automatically enlisted to fight for any so-called cause because of who they are. I certainly don't think that one person wearing high-heeled boots while otherwise presenting as male is setting this alleged cause back 100 years, or, for that matter, at all. If anything, they're moving it forward...well, a minute or so. But every bit helps.

I'm definitely on your side on this one. Sorry that wasn't clear.

[Stiefelchris]

Hi Heather, I am glad you are enjoying your lifestyle and have a wife that supports you in it. You could not ask for much more. I myself do the same thing and my dressing actually started out as a shoe fetish. I simply had to wear women's shoes, but not heels. The everyday shoes women wear was what I wanted to. So I bought booties and boots 2-3in high, block heels, wedge sandals and even shiny dansko clogs. I do wear women's shoes to go out shopping, going to the post office and running errands. If they are more feminine I usually pair them with wide leg jeans. Christi

[Toronto Kristen]

I read this thread with a lot of interest. Yesterday, I went shopping in a local thrift shop while wearing women's jeans and a women's sweater. Unfortunately, I do not have the shoes that would have been right for walking in the slush and ice around the shop. I am going to do a bit of shopping today to rectify that problem.

To pick up on Sabrina's comment, I believe that being able to comfortably, and without fear, go out in public while wearing one or more pieces of women's clothing and shoes will help move the process of acceptance forward.

[Sabrina1013]

I might have to go get myself some cute little boots for when I'm drab. I always wore long pants anyways so nothing would really look outta place :D

[njcddresser]

I've been mixing my wardrobe more and more. I've recently picked up two pairs of great women's jeans that I've been wearing out regularly.

In fact I just got home from a lunch date with my wife where I owe a pair of my lady jeans with my new boots. The boots are gorgeous and have 3" heels. Heading to get my nails done shortly and will have them back on.

I really love being a girl!!

[Brenn]

It is great to see all the other folks here who like mixing up their wardrobe. I have never really cared for boots or heels, but I love wearing ballet flats and mary-janes with my women's jeans or shorts. It is now just my eccentric style and is pretty much accepted by everyone who knows me. I'm a firm believer that the more we get out, the more our style will be accepted (or at least tolerated).

[CynthiaD]

I love mixing obviously feminine things with my male wardrobe. It makes being in drab so much more bearable. I've tried many different variations. Slinky tops, embroidered jeans, red nail polish, all kinds of jewelry, open toed flats, and other stuff. The only thing that gets any attention is the red nail polish, but even that's rare.

You go girl!

[Steph70]

Heather, I don't think you should do that again...and just to make sure you don't, please send those boots to me :) J/K lol. But really...send the boots to me.

I did this once with some short heeled Mary Janes. It was exhilarating. I just went to the store, got a few things and left. I did think everyone was looking at me, but there was only a couple people in the store anyways. I also wear female tops while shopping now...it's easy in the winter under my carhartt. And undies of course...haven't worn male underwear in years...

[lisa_sf]

I, too, have started mixing up the footwear. I have some longer gal jeans, and this has become one of my fave combos....

[Ruby John]

Take a look at http://www.hhplace.org/ The guys there wear fem shoes as guys all the time and will give you some new ideas. Ruby

[Janine cd]

I've worn femme pumps with 2inch heels under drab clothes many times when shopping and have never encountered as much as a single stare.

[luca]

I think this would be such a cool thing to do, the third pair of boots are real cute by the way!

[Julia NZ]

Instead of jeans try tailored or linen wide leg pants with your heels. Much more feminine in my opinion and my usual choice.

[Maria in heels]

Heather...don't you just love the feeling? I have a pair of brown suede boots and I love going out in them too....

[Claire Cook]

I think the "trans people", including myself, would be further advanced if we confidently express ourselves in attire we feel to be appropriate for where we happen to be and not worry so much about what other people think.

Heather, I couldn't agree with you more. If we are confident and comfortable with how we express ourselves -- either partly or fully in femme mode -- I think others ('tho perhaps not everyone...) will start to be comfortable with it.

While I generally don't wear heels (unless getting dressy for dinner), when not at work I do wear ladies' shorts, jeans or sweat pants in drab mode just because they are more comfy. Like others here, I've never have had a negative comment.

[BLUE ORCHID]

Hi Heather, That sounds like a fun thing to try.

[suzanne]

I love it! Isn't it great? I have started wearing heels in drab from time to time and it changes how I feel about everything. Heels constantly remind they are there and it feels wonderful. With pants of the proper length they make my feet look smaller and my legs longer and sexier. And nobody else is looking at what you have on your feet so who cares?

[Jocee]

I love it..... I mostly wear women's shoes now. They are just do more stylish. I've like 3 pair of Dansko's - not the normal "Professional" series, but their more stylish shoes and sandels. They all have two inch heels and are great for my planar fasciitis....