Adventures of SleekHeels

[SleekHeels]

I've really surprised myself this last couple of weeks. First I never thought I'd like any shoe that even vaguely resembled a loafer, but I found myself really drawn to these TanLoafers.jpg . What's more I wore them for a study day at the library (wearing pretty much the outfit2.jpg I posted before). It was a sunny day so I sat on a bench outside to eat my lunch with plenty of people coming and going. No-one batted an eyelid, though I did get a few glances indoors but that was it, far less attention than I expected. I thought the tan loafers made a good choice for wearing courts in public for the first time, and I felt really comfortable wearing them and being seen in them.

Feeling a bit more adventurous I had another study day wearing these StrappyPeeptoes.jpg (I have the black ones, but I included the "oatmeal" colour in the photo to show more detail). Again a similar outfit to above but with different jeans (slightly higher-waisted) and a more tailored black jacket over a white t-shirt). I went to a busy cafe for a drink first. Like before, I noticed a few glances (and I've actually started smiling when that happens now) but otherwise if people noticed they were very discrete about it. I felt way more relaxed than I thought I would wearing these, maybe because I felt the whole outfit worked. I felt so confident I wore them on the bus to the city centre where I browsed in a department store (and bought a couple of brightly coloured t-shirts to match with shoes for future heeling outfits) and waited in my heels for the bus home too. It all felt pretty normal but fantastic as the same time.

I've not had a chance to take photos of me wearing these shoes yet, but I'll try to get around to it eventually.

[SleekHeels]

OK, I've really exceeded my modest shoe budget, but I couldn't resist these brown wedge sandals ( brown wedges2.jpg ) that were half-price at £12. I tried on lots of other styles while I was in the store, and while I was trying on a pair of high-heeled shoe-boots I even got my first comment from another shopper who said "those heels look great!" as I was checking them out in the mirror. I smiled and thanked her and checked out what she was trying on - a pair of gold wedge sandals which looked fabulous on her and I told her so.

Anyway, after I bought my brown wedge sandals and left the store, I was feeling adventurous and it was far too sunny a day to be stuck in boring socks and trainers, so I found a quiet corner to change into my wedges (I was already wearing my bootcut jeans and an open shirt over a t-shirt, all womenswear) and went to a nearby cafe. I ordered a coffee to drink in and found a seat where I stayed for half an hour, drinking my coffee, reading my book, and wearing my heels. I think maybe one other customer, a young lady sat diagonally opposite me, must have noticed my shoes. She was wearing flats, which got me wondering what she was thinking when she saw my sandals... optimistically I'd like to hope that I presented myself well enough that she might have thought "I'm going to wear my heels tomorrow" but perhaps that's just wishful thinking.

[jay jay]

OK, I've really exceeded my modest shoe budget, but I couldn't resist these brown wedge sandals ( brown wedges2.jpg ) that were half-price at £12. I tried on lots of other styles while I was in the store, and while I was trying on a pair of high-heeled shoe-boots I even got my first comment from another shopper who said "those heels look great!" as I was checking them out in the mirror. I smiled and thanked her and checked out what she was trying on - a pair of gold wedge sandals which looked fabulous on her and I told her so.

Anyway, after I bought my brown wedge sandals and left the store, I was feeling adventurous and it was far too sunny a day to be stuck in boring socks and trainers, so I found a quiet corner to change into my wedges (I was already wearing my bootcut jeans and an open shirt over a t-shirt, all womenswear) and went to a nearby cafe. I ordered a coffee to drink in and found a seat where I stayed for half an hour, drinking my coffee, reading my book, and wearing my heels. I think maybe one other customer, a young lady sat diagonally opposite me, must have noticed my shoes. She was wearing flats, which got me wondering what she was thinking when she saw my sandals... optimistically I'd like to hope that I presented myself well enough that she might have thought "I'm going to wear my heels tomorrow" but perhaps that's just wishful thinking.

I just love the wedges.

[roniheels]

Sleekheels,

Congratulations to you on your outing and your choice of outfit and high heels. It sounds like you are more comfortable with every outing and as many of us who wear high heels in public have noticed, many people either don't notice or just don't say anything. Best wishes to you on your future outings.

[SleekHeels]

I just love the wedges.

Thanks! They're a perfect fit and feel very cute to wear, especially on a warm sunny day. Unfortunately the weather's taken a bit of a downturn since then - it looks like Jo'burg winters are nicer than British summers. I hope it brightens up again soon so I can give the wedges another outing.

[SleekHeels]

Sleekheels,

Congratulations to you on your outing and your choice of outfit and high heels. It sounds like you are more comfortable with every outing and as many of us who wear high heels in public have noticed, many people either don't notice or just don't say anything. Best wishes to you on your future outings.

Thanks! You're so right about it feeling more comfortable. I've pushed myself just a little way further outside my comfort zone each time, and afterwards I find myself thinking "wow, did I really just do that?", and increasingly the answer is "yes, and it felt great!". The key for me in building up confidence has been in choosing an outfit and surroundings that I feel most comfortable with to give each outing the best chance of being a success. Best wishes to you and everyone else for successful future outings too.

[JeffB]

Thanks! You're so right about it feeling more comfortable. I've pushed myself just a little way further outside my comfort zone each time, and afterwards I find myself thinking "wow, did I really just do that?", and increasingly the answer is "yes, and it felt great!". The key for me in building up confidence has been in choosing an outfit and surroundings that I feel most comfortable with to give each outing the best chance of being a success. Best wishes to you and everyone else for successful future outings too.

I've found that pushing the envelope can be great fun because of what you accomplish in expanding your horizons. Yes, not only does that bring about a tremendous feeling of satisfaction, it also helps to build up your courage, to embolden you just a little more for future outings. A few years ago, I never would've envisioned myself openly wearing thigh high boots and especially skirts, so I know how good it feels to go beyond my comfort level. Best of luck to you in your future outings!

[SleekHeels]

Well I finally got around to taking photos of the shoes from my last few adventures including the outfit I wore with the black strappy peeptoes. In the shoe photos I pulled up the jeans a bit to reveal the shoes, but I wore them with the jean length like in the outfit photo.

[Shafted]

I'm not a fan of plats but I really like your outfit, Sleekheels.

[Guest]

You went out like that?

[roniheels]

Well I finally got around to taking photos of the shoes from my last few adventures including the outfit I wore with the black strappy peeptoes. In the shoe photos I pulled up the jeans a bit to reveal the shoes, but I wore them with the jean length like in the outfit photo.

I really like the first pair of high heels and I like your outfit and high heels you're wearing with it. What kind of reactions (if any) did you get when you were seen in your outfit and high heels?

[legs777777]

Really nice out fit, very simple looking but very nice, love the heels.

[skirtedvik]

Compliments on the jacket!

[SleekHeels]

I'm not a fan of plats but I really like your outfit, Sleekheels.

I wasn't at all a fan of platforms at first, but there are so many styles with beautiful heels and they do feel fun to walk in, plus I see lots of gorgeous women wearing them, so they've really grown on me.

You went out like that?

I must admit I look at the photo and ask myself the same question, but when I looked in the mirror that day I felt good so I did it. The jeans were freshly ironed so they looked a bit more crisp than they do in the photo (which I took in a bit of a rush).

I really like the first pair of high heels and I like your outfit and high heels you're wearing with it. What kind of reactions (if any) did you get when you were seen in your outfit and high heels?

Thanks roniheels. Unlike previous times when it seemed like nobody even noticed what I was wearing, this time I definitely noticed the glances more. No comments from anyone though. That really didn't bother me since a woman wearing that outfit probably wouldn't get any comments either (but she might get some glances for the shoes).

[Guest]

I must admit I look at the photo and ask myself the same question, but when I looked in the mirror that day I felt good so I did it. The jeans were freshly ironed so they looked a bit more crisp than they do in the photo (which I took in a bit of a rush).

=> that will always surprise me.

In France, if you try to go out with heels with wearing men clothes, people will look at you like if you were a Martian.

We really need to open our mind...

[JeffB]

Hey, SH! Pretty daring outfit if I do say so myself! Just a suggestion, how about trying snug fitting women's bootcut jeans? I think that would make for a, well, sleeker look with your heels.

[SleekHeels]

=> that will always surprise me.

In France, if you try to go out with heels with wearing men clothes, people will look at you like if you were a Martian.

We really need to open our mind...

I don't know about France but when I've been to Mediterranean countries I did get the feeling that gender roles are very fixed. I think if a Martian saw me maybe they wouldn't even realise I was wearing the "wrong" clothes and shoes, it's just us humans who have those preconceptions.

Hey, SH! Pretty daring outfit if I do say so myself! Just a suggestion, how about trying snug fitting women's bootcut jeans? I think that would make for a, well, sleeker look with your heels.

Thanks Jeff. I feel like it's really the shoes that made an otherwise conservative outfit quite daring. And you're right, I do have a better fitting pair of bootcut jeans (the ones in outfit2.jpg) but perhaps that tighter fit felt a bit too bold for me that morning. In the end I chose the ones in outfit3.jpg because I felt the higher waistline and more faded colour suited the black jacket and shoes better (and they did look smarter freshly ironed). I don't think I could ever afford all the different combinations of jeans to complete my wardrobe but, just like shoes, that's what makes it so much more interesting, expressive and fun.

[Guest]

I don't know about France but when I've been to Mediterranean countries I did get the feeling that gender roles are very fixed. I think if a Martian saw me maybe they wouldn't even realise I was wearing the "wrong" clothes and shoes, it's just us humans who have those preconceptions.

=> Exactly! My English is not very good to explain that.

In France, if you change your clothes "look" for something approaching femal one, the fisrt think of majority people is that you are an homosexual, no more.

It is also possible to be assaulted or offended in some countries..

[tallguyinheels]

Excellent look in the Jeans and Platform heels... You know, I might just give it a try - though I'll need to find a large size... 15. I mostly spend my time in shoes like my avatar, in women's jeans or men's chinos or slacks... occasionally venturing in a skirt (seek out "Skirting the Envelope" here. A platform will give me a towering profile however, as I am 195cm in my stockings.

[SleekHeels]

I had another fun day out in heels this week, first time in a while I've had the chance. I wore my 4" black leather ankle boots with black bootcut jeans and a blue & white checked shirt worn open over a white t-shirt.

First stop was a chemist (drug store) to buy some face moisturiser. The girl behind the cash desk was quite short (but very cute) and maybe she likes wearing heels but I don't blame her for not wearing them at work being on her feet all day. Then to the coffee shop to grab a take-away coffee. If anyone noticed my heels so far they hid it pretty well.

Next a 5 minute walk along a main road to the library where I spent the morning studying. I popped out for a break and sat on a bench to eat my lunch, and me and my heels seemed pretty much invisible. When I went back inside there was a girl wearing the most gorgeous brown suede boots just over the knee and with beautifully elegant heels maybe 4". She was sat reading a magazine, I politely said "Excuse me, I just wanted to say you look fabulous in those boots, have a lovely day" and she smiled and said "Thank you, that's very sweet". I know I would have been in heaven just wearing boots like that, let alone receiving a compliment.

Later in the afternoon I walked about 10 minutes to a small outdoor shopping mall. I popped into another chemist store to buy some knee-high tights (to replace the thicker socks I was wearing), then to the clothing store to look for the tan version of some very cute black suedette shoe-boots I'd bought last week. I found them, the tan colour looked really cute peeping out from under my black bootcut jeans, but I wanted to see how they'd look with black skinny jeans (and if I could pull off that bolder look). I took a couple of different size jeans to the changing rooms, the young male attendant gave me a slightly curious look but treated me just like any other customer. The jeans didn't fit nicely (too low on the waist) but back out in the store I found a pair of black jeggings, tried those in the changing rooms and they fit and looked surprisingly flattering. I had nice little chat with the very sweet checkout girl about heels and jeans.

I went for a little walk in a nearby park (still in my old black ankle boots). My feet were really aching by this time because the boots don't have any padding inside. Today I tried inserting some foam insoles which were a little better but not great, so I added a pair of gel inserts under the ball of each foot and that seems much better.

Now I just need to build up the confidence to wear my new shoe-boots on full display with the super-skinny jeggings. I love the look and it makes me feel good, if anything I should feel more ashamed wearing my sloppy guys jeans/trainers rather than taking pride in my appearance.

[SleekHeels]

I haven't posted here for a while but I have been having plenty of adventures in heels. Here are some of the more memorable days/outfits from memory (sorry, no full outfit photos, my camera's been broken for a while):

1) My strappy black peeptoes ( black strappy.jpg ) with black opaque tights, a dark orange mini-skirt and black poloneck top under my denim jacket, with an orange scarf. This was my first time daring to wear a skirt, I only did it because I felt good about the whole outfit. It turned out I felt far more confident than I expected. and that evening I went back to the store where I'd bought the skirt and heels to say thanks to the shop assistant and show her the outfit.

2) My brown boots ( brown boots 2.jpg ) with black leggings and a light brown wool dress (really just looks like a long jumper) with my denim jacket. I noticed a few glances but nothing that made me feel at all uncomfortable, even exchanged a few smiles.

3) My blue peeptoes ( blue-peeptoes.jpg ) with a matching poloneck jumper and black trouser-suit. At lunchtime the sales assistant in the sandwich shop said "looking good!" which really took me by surprise so all I could manage was a brief "Thanks". (Note to self, compliments are rare, I'll make more of an effort to be more appreciative in future).

4) The same brown boots as #2 above but with blue skinny jeans and a cream top under a smart tweed jacket. Previously I'd tried the same look with my tall flat-heeled brown boots and felt practically invisible all day. The high-heeled boots definitely sharpened up the outfit and got a few discrete glances.

5) My grey court stilettos ( grey courts.jpg ) with black bootcut jeans and a white shirt under a grey v-neck jumper. I changed into my flat shoes to go to a concert in the evening, but waiting for the doors to open I saw a few women looking good in their heels so, feeling a little envious, I talked myself into changing back into my heels for the rest of the evening, which was fine and uneventful but exciting to be in heels.

6) Brown ankle boots ( brown ankle boots.jpg ) with blue skinny jeans and a dark brown ribbed poloneck jumper. This was my first time wearing high-heeled ankle boots without the cover of bootcut jeans and felt quite daring, perhaps even moreso than when I wore my leggings/skinny-jeans tucked into my taller boots. Despite my apprehension beforehand I felt pretty confident as the day went on, definitely a feel-good look for me.

Then I wanted to explore the boundaries a bit more so I tried:

7) My tall grey boots ( greyboots.jpg ) with black fishnet tights, a black skirt (just above the knee) and white shirt under a grey v-neck jumper. Outdoors I wore my 3/4-length black coat. I generally felt good but with an undercurrent of self-consciousness throughout the day.

8 ) My tall green boots ( Wallis boots.jpg ), the same black skirt as #7 above but with sheer black tights instead of the fishnets, and a black poloneck top under a green knitted jumper. Again outdoors I wore my 3/4-length black coat. The day included a visit to the cafe, and a bus ride to a concert in the evening, all of which were great. I got a bit carried away and stayed in the outfit for the journey home in the evening, which was uneventful but reminded me of the horrible way men look at women sometimes.

I must admit those last two outfits must've presented the image of a guy trying to be a woman, rather than just a guy in heels, though I didn't wear any make-up or change my way of speaking to anyone (and I was still addressed as "sir" which was fine). I'll probably revert to a more causal guy-in-heels look most of the time, but it was fun to feel a bit more glamorous and in the right surroundings I'll occasionally do that again too.

[StockingTop]

I haven't posted here for a while but I have been having plenty of adventures in heels. Here are some of the more memorable days/outfits from memory (sorry, no full outfit photos, my camera's been broken for a while):

1) My strappy black peeptoes ( black strappy.jpg ) with black opaque tights, a dark orange mini-skirt and black poloneck top under my denim jacket, with an orange scarf. This was my first time daring to wear a skirt, I only did it because I felt good about the whole outfit. It turned out I felt far more confident than I expected. and that evening I went back to the store where I'd bought the skirt and heels to say thanks to the shop assistant and show her the outfit.

2) My brown boots ( brown boots 2.jpg ) with black leggings and a light brown wool dress (really just looks like a long jumper) with my denim jacket. I noticed a few glances but nothing that made me feel at all uncomfortable, even exchanged a few smiles.

3) My blue peeptoes ( blue-peeptoes.jpg ) with a matching poloneck jumper and black trouser-suit. At lunchtime the sales assistant in the sandwich shop said "looking good!" which really took me by surprise so all I could manage was a brief "Thanks". (Note to self, compliments are rare, I'll make more of an effort to be more appreciative in future).

4) The same brown boots as #2 above but with blue skinny jeans and a cream top under a smart tweed jacket. Previously I'd tried the same look with my tall flat-heeled brown boots and felt practically invisible all day. The high-heeled boots definitely sharpened up the outfit and got a few discrete glances.

5) My grey court stilettos ( grey courts.jpg ) with black bootcut jeans and a white shirt under a grey v-neck jumper. I changed into my flat shoes to go to a concert in the evening, but waiting for the doors to open I saw a few women looking good in their heels so, feeling a little envious, I talked myself into changing back into my heels for the rest of the evening, which was fine and uneventful but exciting to be in heels.

6) Brown ankle boots ( brown ankle boots.jpg ) with blue skinny jeans and a dark brown ribbed poloneck jumper. This was my first time wearing high-heeled ankle boots without the cover of bootcut jeans and felt quite daring, perhaps even moreso than when I wore my leggings/skinny-jeans tucked into my taller boots. Despite my apprehension beforehand I felt pretty confident as the day went on, definitely a feel-good look for me.

Then I wanted to explore the boundaries a bit more so I tried:

7) My tall grey boots ( greyboots.jpg ) with black fishnet tights, a black skirt (just above the knee) and white shirt under a grey v-neck jumper. Outdoors I wore my 3/4-length black coat. I generally felt good but with an undercurrent of self-consciousness throughout the day.

8 ) My tall green boots ( Wallis boots.jpg ), the same black skirt as #7 above but with sheer black tights instead of the fishnets, and a black poloneck top under a green knitted jumper. Again outdoors I wore my 3/4-length black coat. The day included a visit to the cafe, and a bus ride to a concert in the evening, all of which were great. I got a bit carried away and stayed in the outfit for the journey home in the evening, which was uneventful but reminded me of the horrible way men look at women sometimes.

I must admit those last two outfits must've presented the image of a guy trying to be a woman, rather than just a guy in heels, though I didn't wear any make-up or change my way of speaking to anyone (and I was still addressed as "sir" which was fine). I'll probably revert to a more causal guy-in-heels look most of the time, but it was fun to feel a bit more glamorous and in the right surroundings I'll occasionally do that again too.

I'm sorry I'll need to see actual pictures of you in the outfits before I pass comment (especially the fishnets )

[roniheels]

You've got a nice collection there and some interesting fashion ideas. Try some of your ideas and see how comfortable you are with your complete outfit.

[kikepa]

Way to go, SleekHeels!

[SleekHeels]

Another cool day... wore my brown wedges ( snake-wedge-courts.jpg ) with black super-skinny jeans to show them off rather than hide them under long bootcut jeans. A brown top under a black cardigan made for an everyday outfit that really blended in to my surroundings.

Sure I got noticed but any reactions I got were nothing more than brief glances, and as usual most people didn't seem to notice at all. The cafe was quite busy so I had to ask before sharing a table but I've done that many times and it's always been fine.

[HappyFeat]

Like you, I haven't posted here in a while and so I missed the bulk of your thread. The outfits you described above all sound sharp and your shoes are all very nice. My favorites however were the stiletto loafers from last summer. Very nice and quite stylish. You do quite well and don't you love the feeling of just puting on what you want to wear and going with it?

[SleekHeels]

Thanks, I wore those stiletto loafers ( tan loafers.jpg ) again last week with a great pair of dark blue bootcut jeans I found in the sales. I've also had a couple more outings with my grey courts ( grey1.jpg ) and black slingbacks ( black slingbacks.jpg ), again both with bootcut jeans. You're right it's a great feeling to just go ahead and wear outfits that just feel "right".

As soon as I get the replacement battery for my camera I'll try to reassemble some of the outfits and have a little photo shoot.

[SleekHeels]

I'd like to keep this thread more up-to-date but most of my little adventures (and I have been keeping up my heeling) seem quite unremarkable. I did make a couple of minor breakthroughs this week though: 1) I went to the supermarket wearing my black leather wedges with bootcut jeans and a black tshirt. The breakthrough for me was the short sleeves as I have quite hairy arms and I've always preferred to hide them under long sleeves when wearing heels - it's not like I'm trying to hide the fact that I'm a guy by wearing long sleeves, but it's the first time I've really felt I've been able to blend an overtly masculine feature with my heels and feel comfortable with the image I was projecting. I mostly got no reactions at all, just one little girl who stared at me with a look of "happy disbelief". 2) A trip to the mall wearing my black suedette wedge sandals with bootcut jeans, a black waterfall cardigan over a white tshirt, and a small black shoulder bag. Despite the fact that it had just been raining I was lucky to find a parking space not too far from one of the department store entrances. I didn't hesitate at all, I just got out of the car and walked into the store. I wandered around the home furnishings section, which was busier than I expected (actually that's nicer than if it had been really quiet). Then I walked through the mall and bought a hairband from a clothing store. The queue was really slow so all the other customers (all young women) had plenty of chance to notice me but if they did nobody showed any reaction. The till clerk was very polite and friendly and treated me just like any other customer, which was nice. Next stop was another store where I browsed the clothing sale racks but didn't see anything I really liked. As I checked out some of the heels a couple of young women stepped aside and whispered between themselves but very discretely and not in a way that offended at all. I didn't see any shoes I liked so I left that store and found a bench in the seating area where I changed into my new hairband (previously I had my shoulder-length hair tied back, the new hairband went across above my forehead and left my hair in a more open and flowing style which was fun for the rest of the shopping trip). Next I walked to a store to buy some body lotion (which I mostly use on my feet because I think beautiful skin is an essential part of the look with high-heeled courts and sandals). The sales assistant had no hesitation in asking me if I needed any help, and again the till clerk was very natural and friendly. I headed back towards the department store and browsed the home furnishings some more until the rain stopped before heading home.

[Steve63130]

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. Steve

Edited July 10, 2012 by Steve63130

[JeffB]

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!

Edited July 11, 2012 by JeffB