Adventures of SleekHeels

[SleekHeels]

Interesting outings - thanks for sharing! You must have acted pretty confidently, and as many of us have preached, that's the key to success. It's much more fun to be out and about enjoying the freedom of wearing the heels you like, instead of hiding them inside and feeling constrained. The more men are seen wearing heels in public, the faster we can educate the unwashed masses.

Thanks Steve, I did feel confident throughout and I wasn't striving to feign confidence to overcome fear, it was a really relaxed confidence and the sense of "enjoying the freedom of wearing the heels you like" just like you describe.

Hey, SleekHeels! Bravo on your latest outings! Regarding your shoes, I just LOVE those black wedges to death! I'd gladly wear those (if they came in my size), preferably with a short skirt in a New York minute! Keep those adventures coming!

Thanks Jeff. Those wedges were a bargain find for £10 in the sales, with real leather uppers and very comfortable to wear. I think my legs need a bit of a tone-up before I'd consider a short skirt, but I may try the wedges with my cropped jeans if we ever get a sunny day here!

[SleekHeels]

Opportunities for adventures in heels have been few and far between lately, mostly just the odd trip to the supermarket for shopping. But today I managed to achieve one of my targets which was to go out in my heels with skinny jeans. I wore my grey courts with black jeggings and my blue-and-white checked shirt over a white t-shirt. First stop was a cafe for lunch. I got nothing more than a few glances, perhaps because I was sitting, but it was definitely more noticeable than usual because the skinny jeans show off my heels a lot more than my bootcut jeans. Then I walked to a nearby bus stop and took the bus to Oxford Street - it was a pretty uneventful bus ride and I'm not sure anyone even noticed my heels. I walked along part of Oxford Street popping into various stores to browse clothes and shoes. In a large department store I saw a cardigan I liked and took it to the changing rooms, where the attendant told me I had to go to the men's changing room to try it on. As a guy in heels it doesn't bother me using the men's changing rooms, much like I'll always use the men's toilets rather than intrude on women's space, but in smaller stores where they only have one changing area (for women) I've never had a problem with other customers, if anything they're usually a little curious but very accepting. In any case I didn't fancy going all the way up to the men's department so I just put the cardigan back on the rack and left. For my first experience in skinny jeans, I definitely felt that I was noticed more, actually more so by women who I think were more astute at picking up on overall look and weren't afraid to show a reaction. I think the guys who noticed probably saved their double-takes for when I couldn't see them. Maybe the boldness of the look exuded more confidence, which women tended to react to more positively and men more negatively, that's my hunch anyway. I did get a comment from one woman who smiled and asked me if my outfit was for some sort of art project. I said that it's not, it's just a personal social statement, which she said was great. I thanked her for taking the time to speak to me. Other than my usual boot-cut jeans I've worn leggings with high-heeled knee-high boots before, but today's skinny-jeans with court shoes worn barefoot felt more bold for sure. In a way it wasn't as daring as when I once wore my orange and black dress (just above the knee) with a black jacket, sheer black tights and my black slingbacks and small shoulder-bag, because my feeling then was that people were perceiving me as a transsexual (and not a very convincing one), whereas today's skinny-jeans outfit was more androgynous and pushed my guy-in-heels boundaries further than before. Overall I really enjoyed wearing my heels more visibly with the skinny jeans and I'll definitely do it again, it was fun. Thanks for reading.

Edited August 15, 2012 by SleekHeels

[Shafted]

A good read, Sleekheels. I think a lot of guys are after that androgynous look that wear heels. It's a great look to wear heels with yet it still has that degree of, "Yea, I'm a guy in heels and I'm looking good in them."

[Steve63130]

I agree with both of you about the androgynous look. I doubt if I can ever achieve it, though. My facial features are just too masculine and I don't like having long hair (but I'm lucky to have any hair!). But the androgynous look is great if you can achieve it. Steve

[SleekHeels]

Thanks Shafted. Yes, it's only through the forum that I learnt that I can be a "guy in heels" and not feel the compelling futility of having to masquerade as a woman in heels. I guess it's one thing to cross gender boundaries, another thing to challenge and redefine them.

Steve, I do have long hair and I like it, though perhaps it's been a bit of a security blanket for me as I'm not sure I'd have taken my first steps heeling if I'd had short hair. Some women seem to have some very boyish haircuts these days, but they can get away with it because they have the feminine facial features. I also have masculine facial features and it is hard to find a balance. I just try to focus on a coordinated outfit, and my "dress like a girl who's trying to dress like a boy" approach is the closest I can get to an overall blended image that works. It's just like the 70's but all the funky clothes are in the women's section!

[Shafted]

I guess it's one thing to cross gender boundaries, another thing to challenge and redefine them.

Very profound. I'll remember that one.

[bluejay]

SleekHeels, that was a nice heeling event. I always like to dress like a man but who likes to wear heels with men's fashions. I am always ready to show off my heels to the rest of the world. Happy Heeling, bluejay

[SleekHeels]

I have been intermittently keeping up my heeling adventures and here are a couple of my latest outfits that I wore out and about this week: 1) Turquoise sandals with 6" heel / 1½" platform, with turquoise tshirt, black bootcut jeans and blue denim jacket. It's months since I painted my toes, showing them off with sandals in another heeling milestone for me and I didn't want to wait until next summer to try it. 2) Beige clog mules with 4" heel / 1" platform, with dark blue bootcut jeans and a faux sheepskin jacket over a cream-coloured top. The back of my ankles were really sore after spending the previous day walking miles (in guy shoes go figure) so it seemed the perfect opportunity to wear these clog mules. No reactions other than glances (and one exchange of smiles). With the first outfit everyone's eyes seemed drawn to the turquoise sandals, with the second outfit they hardly seemed to notice the clogs and seemed more interested in the jacket (which I bought for around £20 in the sales a couple of winters ago).

[JeffB]

Bravo, SleekHeels! Both outfits looked great as you put them together well! I like the first picture most, really cool!

[Shafted]

I like your style Sleekheels. I agree with Jeff, both outfits look great.

[FreshinHeels]

Nice look! Can I have some of you're hair?

[Steve63130]

Good coordination, Sleekheels. I like the way you put the outfits together. Steve

[CrazyIcecap]

Looks really great! Nice outfits!

[SleekHeels]

Thanks guys, all your comments are very much appreciated. I was thinking of trying variants of that first outfit, replacing the turquoise with red and royal blue shoes+tshirt. Another option is to replace the black trousers with white, though perhaps that's more of a spring/summer look. FreshinHeels, my hair's taken 5 years to get how it is now, I do enjoy the extra confidence that it gives me for heeling but I feel like I'm cheating a little and I'm not even sure if I'd have ever worn my heels with a crew-cut, I really admire the confidence of guys who can pull that off (even though there are lots of women with boyish haircuts, I'm not sure if that makes it any easier).

[bluejay]

Nice outfits SleekHeels. Well put together. I like the first one best. I like your red pedi on your feet with the sandals. That is a favorite look of mine since I also have a red pedi too. keep up the good work! Happy Heeling, bluejay

[Mr. X]

Way to go Sleek! Both outfits look great!

[Puffer]

Thanks guys, all your comments are very much appreciated.

I was thinking of trying variants of that first outfit, replacing the turquoise with red and royal blue shoes+tshirt. Another option is to replace the black trousers with white, though perhaps that's more of a spring/summer look.

FreshinHeels, my hair's taken 5 years to get how it is now, I do enjoy the extra confidence that it gives me for heeling but I feel like I'm cheating a little and I'm not even sure if I'd have ever worn my heels with a crew-cut, I really admire the confidence of guys who can pull that off (even though there are lots of women with boyish haircuts, I'm not sure if that makes it any easier).

You look good in both outfits, SleekHeels; well done!

Having followed your exploits, I had realised that you were quite adventurous with your footwear in public and, on seeing these latest pics, I think I can see why you have a 'head start' (no pun intended!). Your very long hair is obviously distinctive and an uncommon look on any man, so you are already making it very obvious to any onlooker that you are intentionally 'different' in your chosen appearance - and might well be perceived as eccentric, or whatever term comes to mind (and I do not imply any criticism).

Having chosen that 'different' look, it is not a huge step (again, no pun!) to your wearing more unusual clothes and, of course, shoes, with or without heels. In other words, you have achieved an overall co-ordinated appearance which is unusual and distinctive, but in which the shoes merely play a supporting role (OK - that might be a pun!), however important. Without your hair, I think you might get a different (and possibly less accepting) reaction, as you seem to realise.

As has been said here many times before, co-ordination is the key. Just slinging on some heels with a vaguely appropriate pair of trousers is not enough, as any onlooker is likely to have an adverse view of one's fashion sense or self-respect. Growing your hair for five years is, perhaps, an extreme measure (and I could not and would not do it) but it has certainly added to your credibility and self-confidence.

In contrast (and with no criticism intended), I am surprised how many heeling members have facial hair. Surely the least appropriate fashion accessory to go with anything overtly feminine and a potential trigger for some ridicule? It must take some balls to combine those looks.

[roniheels]

SleekHeels ... I really like your high heels and your coordinated outfits. Your combo looks stylish and comfortable.

[SleekHeels]

Thanks for your comments guys. Sure I think the hair does play a part in creating an overall impression that blends in with what people expect to see. My aim isn't to "pass" as a woman though, and I've only every been addressed as "sir" which I like because I'm not being misclassified as anything other than a guy who happens to dress differently from the male norm (but actually quite conventional to the female norm). That's the thing, they're not "unusual" outfits, they're just unusual for men. I admit that places me on the more subtle end of the spectrum while others can be far more extrovert in creating looks that clash the norms more explicitly. I admire that too, we're all breaking new ground in different ways and I think it's not necessarily "easier" or "harder" to be at any point on the spectrum, we just do what we feel happy and confident about. It always takes more guts to go outside your personal comfort zone, wherever that comfort zone may be. Not exactly "adventures" but here are a couple of incidents from the last few weeks: 1) I went to one of these sportswear discount warehouse stores. I decided to wear my grey courts with black skinny jeans and a grey short-sleeve polo-shirt (womens, a nice fit, not at all baggy). As I was browsing this guy walked past, mumbled "disgusting!" and was out of sight before I'd even processed what he'd said. That's got to be far stranger behaviour than wearing nice shoes. 2) I was in a public washroom drying my hands with my back to the door. I was wearing my new black suedette courts (5" heel with a 1" hidden platform), black opaque tights, stretch skirt (just above the knee) and a black turtleneck top under my blue denim jacket). I heard the door open and then a guy said out loud "Oh, am I in the wrong room?". I turned and casually said "No, you're in the right room mate!". He seemed totally relaxed about it in an oh-well-these-things-happen kind of way. Actually buying those black courts was a pretty cool shopping experience. In the store I found a pair on the rack in my size and tried them on but they were too small which was strange because I've already bought the same style in blue and oatmeal and they fit great. Luckily I found another pair in my size and they fit just fine. I took them to the cash desk and after paying I asked the assistant "is it ok if I change into them before I leave?" and she said "yes, of course" just like she'd say to any other customer. I changed into them and they looked so stylish with my womens bootcut jeans. As I passed her on the way out I asked "So, what do you think?" and she said they looked really cool, asked if they were comfortable to wear and said she'll have to buy a pair. I said thanks and wished her a good night. Buying boring guy shoes was never this good!

[Steve63130]

Thanks for sharing your recent experiences. Sounds like you had fun and that's the main thing! Steve

[Gudulitooo]

Sleekheels, I think you should thank the people that recognise you as a man in these outfit, because I was not able to see this on the pictures. I mean, I thought you find these pictures on a magazine and reprinted them here to show what you wore. LOL. Now after reading, WOW. Your outfits are very stylish, and should you be a woman, you would definetely be sexy ! (thanks to the jeans). These looks are reminding me of the seventies (at least what I saw in the movies folks I was not born at the time) - did you also wear large black glasses ? - which could explain why people have no difficulties recognizing you as a guy and smiling at old memories - a lost paradise. Eric

[bluejay]

I will echo what Steve said. You had some nice heeling events

Thanks for your comments guys.

Sure I think the hair does play a part in creating an overall impression that blends in with what people expect to see. My aim isn't to "pass" as a woman though, and I've only every been addressed as "sir" which I like because I'm not being misclassified as anything other than a guy who happens to dress differently from the male norm (but actually quite conventional to the female norm). That's the thing, they're not "unusual" outfits, they're just unusual for men. I admit that places me on the more subtle end of the spectrum while others can be far more extrovert in creating looks that clash the norms more explicitly. I admire that too, we're all breaking new ground in different ways and I think it's not necessarily "easier" or "harder" to be at any point on the spectrum, we just do what we feel happy and confident about. It always takes more guts to go outside your personal comfort zone, wherever that comfort zone may be.

Not exactly "adventures" but here are a couple of incidents from the last few weeks:

1) I went to one of these sportswear discount warehouse stores. I decided to wear my grey courts with black skinny jeans and a grey short-sleeve polo-shirt (womens, a nice fit, not at all baggy). As I was browsing this guy walked past, mumbled "disgusting!" and was out of sight before I'd even processed what he'd said. That's got to be far stranger behaviour than wearing nice shoes.

2) I was in a public washroom drying my hands with my back to the door. I was wearing my new black suedette courts (5" heel with a 1" hidden platform), black opaque tights, stretch skirt (just above the knee) and a black turtleneck top under my blue denim jacket). I heard the door open and then a guy said out loud "Oh, am I in the wrong room?". I turned and casually said "No, you're in the right room mate!". He seemed totally relaxed about it in an oh-well-these-things-happen kind of way.

Actually buying those black courts was a pretty cool shopping experience. In the store I found a pair on the rack in my size and tried them on but they were too small which was strange because I've already bought the same style in blue and oatmeal and they fit great. Luckily I found another pair in my size and they fit just fine. I took them to the cash desk and after paying I asked the assistant "is it ok if I change into them before I leave?" and she said "yes, of course" just like she'd say to any other customer. I changed into them and they looked so stylish with my womens bootcut jeans. As I passed her on the way out I asked "So, what do you think?" and she said they looked really cool, asked if they were comfortable to wear and said she'll have to buy a pair. I said thanks and wished her a good night. Buying boring guy shoes was never this good!

You had some nice heeling events. Don't let the comment of one JA get you down. Wear your heels with pride as I do always!

Happy Heeling,

bluejay

[SleekHeels]

Sleekheels,

I think you should thank the people that recognise you as a man in these outfit, because I was not able to see this on the pictures. I mean, I thought you find these pictures on a magazine and reprinted them here to show what you wore. LOL. Now after reading, WOW. Your outfits are very stylish, and should you be a woman, you would definetely be sexy ! (thanks to the jeans). These looks are reminding me of the seventies (at least what I saw in the movies folks I was not born at the time) - did you also wear large black glasses ? - which could explain why people have no difficulties recognizing you as a guy and smiling at old memories - a lost paradise.

Eric

Thanks Eric. No I wasn't wearing large black glasses, but with heels and bootcut jeans I do get that seventies revival feeling when outfits were just funky and male or female didn't seem to matter so much. I missed it the first time around too. Maybe from a distant casual glance I could be momentarily be mistaken for a woman, but my face is unmistakably male and I don't change my voice at all, so for those I interact with there's no doubt I'm a "sir". If they called me "ma'am" I'd feel like they're missing the point that I'm challenging gender prejudice.

[SleekHeels]

So yesterday was a fun and interesting day. I've been wanting to debut my blue suedette courts (5" heel, 1½" hidden platform) with a matching blue blouse and tailored black jacket. I couldn't decide between the jacket's matching black trousers (tailored but quite a slim fit with a bootcut which givs them quite a funky look) or a black pencil skirt. In the end I went for the skirt as it'll be plenty cold enough for trousers as the winter sets in, plus I really wanted to show off the shoes (worn with sheer tights) and not just have them peeping out from under trousers I accessorised with some inexpensive silver jewelry - a watch, bracelet, necklace and a couple of rings, and a black satchel-style handbag. I was passing through Kings Cross train station and had a couple of pleasant encounters. The first was a young lady who came up to me and asked if I work there (I was carrying a folder and I guess I looked quite business like). At first I thought maybe she didn't notice I'm a guy, at least until she'd already started talking to me. On reflection it was probably pretty obvious I'm a guy but what with equal opportunities employment she didn't seem at all phased about approaching me - sure she was a bit embarassed when I told her I don't work there, but I've had that happen when I'm wearing regular guy clothes and she reacted much the same. The second encounter was near a prominent statue in the station, which features a kissing couple with the woman wearing some rather lovely heels. As I was looking to take a photo of the statue a young lady approached me to ask for directions. As she went to leave I asked her if she wouldn't mind taking a photo of me with the statue. I specifically asked her to make sure she got my heels and the statue's heels. I explained that I have some friends who don't believe I go out dressed like this so I need a photo. She said I looked fabulous which totally made my day. I thanked her and said "so do you" as she turned to leave (she had the most beautiful eyes)... and I have a cool photo. Today I went for a more androgynous look (no heels I'm afraid), my dark brown flat knee-high boots with black leggings and a black turtleneck top under a petrol blue loose-knit jumper. It certainly felt like I got noticed a lot less than the previous day, but the few strangers who did notice seemed less inhibited about showing it with a smile.

[JeffB]

WOW! What an outfit you displayed in that photo! You looked absolutely amazing! Bravo to you, my friend! You nailed it with your stunning ensemble, and then some! Color me suitably impressed!

[skirtedvik]

So yesterday was a fun and interesting day. I've been wanting to debut my blue suedette courts (5" heel, 1½" hidden platform) with a matching blue blouse and tailored black jacket. I couldn't decide between the jacket's matching black trousers (tailored but quite a slim fit with a bootcut which givs them quite a funky look) or a black pencil skirt. In the end I went for the skirt as it'll be plenty cold enough for trousers as the winter sets in, plus I really wanted to show off the shoes (worn with sheer tights) and not just have them peeping out from under trousers I accessorised with some inexpensive silver jewelry - a watch, bracelet, necklace and a couple of rings, and a black satchel-style handbag.

I was passing through Kings Cross train station and had a couple of pleasant encounters. The first was a young lady who came up to me and asked if I work there (I was carrying a folder and I guess I looked quite business like). At first I thought maybe she didn't notice I'm a guy, at least until she'd already started talking to me. On reflection it was probably pretty obvious I'm a guy but what with equal opportunities employment she didn't seem at all phased about approaching me - sure she was a bit embarassed when I told her I don't work there, but I've had that happen when I'm wearing regular guy clothes and she reacted much the same.

The second encounter was near a prominent statue in the station, which features a kissing couple with the woman wearing some rather lovely heels. As I was looking to take a photo of the statue a young lady approached me to ask for directions. As she went to leave I asked her if she wouldn't mind taking a photo of me with the statue. I specifically asked her to make sure she got my heels and the statue's heels. I explained that I have some friends who don't believe I go out dressed like this so I need a photo. She said I looked fabulous which totally made my day. I thanked her and said "so do you" as she turned to leave (she had the most beautiful eyes)... and I have a cool photo.

Great outfit!Wouldn't mind a better resolution/photo.Keep up freestyling!

[HenriHH]

So yesterday was a fun and interesting day. I've been wanting to debut my blue suedette courts (5" heel, 1½" hidden platform) with a matching blue blouse and tailored black jacket. I couldn't decide between the jacket's matching black trousers (tailored but quite a slim fit with a bootcut which givs them quite a funky look) or a black pencil skirt. In the end I went for the skirt as it'll be plenty cold enough for trousers as the winter sets in, plus I really wanted to show off the shoes (worn with sheer tights) and not just have them peeping out from under trousers I accessorised with some inexpensive silver jewelry - a watch, bracelet, necklace and a couple of rings, and a black satchel-style handbag.

I was passing through Kings Cross train station and had a couple of pleasant encounters. The first was a young lady who came up to me and asked if I work there (I was carrying a folder and I guess I looked quite business like). At first I thought maybe she didn't notice I'm a guy, at least until she'd already started talking to me. On reflection it was probably pretty obvious I'm a guy but what with equal opportunities employment she didn't seem at all phased about approaching me - sure she was a bit embarassed when I told her I don't work there, but I've had that happen when I'm wearing regular guy clothes and she reacted much the same.

The second encounter was near a prominent statue in the station, which features a kissing couple with the woman wearing some rather lovely heels. As I was looking to take a photo of the statue a young lady approached me to ask for directions. As she went to leave I asked her if she wouldn't mind taking a photo of me with the statue. I specifically asked her to make sure she got my heels and the statue's heels. I explained that I have some friends who don't believe I go out dressed like this so I need a photo. She said I looked fabulous which totally made my day. I thanked her and said "so do you" as she turned to leave (she had the most beautiful eyes)... and I have a cool photo.

I agree with JeffB. You look terrific. Thanks for sharing.

Henri

Today I went for a more androgynous look (no heels I'm afraid), my dark brown flat knee-high boots with black leggings and a black turtleneck top under a petrol blue loose-knit jumper. It certainly felt like I got noticed a lot less than the previous day, but the few strangers who did notice seemed less inhibited about showing it with a smile.

[Puffer]

The statue is at St Pancras railway station (not at Kings Cross - next door). Nice outfit, by the way!

[SleekHeels]

WOW! What an outfit you displayed in that photo! You looked absolutely amazing! Bravo to you, my friend! You nailed it with your stunning ensemble, and then some! Color me suitably impressed!

Approval from a trailblazer such as yourself means a lot Jeff, thanks!

Great outfit!Wouldn't mind a better resolution/photo.Keep up freestyling!

Thanks skirtedvik. I'm afraid the resolution was the best my mobile phone camera could do.

The statue is at St Pancras railway station (not at Kings Cross - next door).

Nice outfit, by the way!

Thanks Puffer. I stand corrected on the station's name.

[ilikekicks]

Sleeks.. I like the suit! Actually, I think I might pick up something similar next week as I have events to attend that require a better dress code then I normally wear. I dig the blue suede shoes too! -Ilk