Adventures of SleekHeels

[Steve63130]

Nice outfit, SH, but there's too much makeup on your face and it looks a bit blurry. :silly: Just being goofy... Steve

[SleekHeels]

Nice outfit, SH, but there's too much makeup on your face and it looks a bit blurry.

Yes, I was trying to copy those girls who put on their makeup on a bouncy train so effortlessly, but I guess I've not quite mastered the technique yet!

Bravo, SH! Bravo! That was a sharp and stylish outfit that you could wear just about anywhere. The wedge sandals look especially cool. I'm thinking I could find a white pencil skirt somwhere, but since September is right around the corner, I worry about wearing white after Labor Day.

Thanks Jeff. I must admit I do feel a lot more comfortable wearing white during spring or summer, but that's usually down to the weather more than anything else. I feel almost equally reluctant to wear black on a sunny summer's day. Maybe all those bright and breezy washing powder commercials have biased me. In any case, it's not a "rule" that I feel I have to conform to, just a general preference. I often wear white shirts all year round without even thinking about it, it's just white blazers, skirts and trousers that seem more seasonal, perhaps even more so than white heels.

[JeffB]

Yes, I was trying to copy those girls who put on their makeup on a bouncy train so effortlessly, but I guess I've not quite mastered the technique yet!

It must be a special talent women have. I actually cringe when I see women expertly working mascara wands on moving trains and never manage to poke out an eye. It's amazing!

Thanks Jeff. I must admit I do feel a lot more comfortable wearing white during spring or summer, but that's usually down to the weather more than anything else. I feel almost equally reluctant to wear black on a sunny summer's day. Maybe all those bright and breezy washing powder commercials have biased me. In any case, it's not a "rule" that I feel I have to conform to, just a general preference. I often wear white shirts all year round without even thinking about it, it's just white blazers, skirts and trousers that seem more seasonal, perhaps even more so than white heels.

It's funny, but I'm more comfortable wearing black as that's a color that can be worn all year long, even in summer despite the concerns about black absorbing heat while lighter colors don't. If I'm hesitant about wearing white, it's because I fear an accident while eating and getting a stain which can be traumatic.

[Curt]

I couldn't put eye makeup on in the subway, ill poke my eye out. Some women are amazing at it. I saw a women putting on fondation on with a brush, whiile driving merging in on the freeway(hwy 401 in Toronto, 8 lane). Crazy! I get all that shit done before I leave the house. Can't be in publkic without it, and 5" heels of course!

[Mr. X]

Nice outfit Sleek! You wear it well!

[SleekHeels]

It's funny, but I'm more comfortable wearing black as that's a color that can be worn all year long, even in summer despite the concerns about black absorbing heat while lighter colors don't. If I'm hesitant about wearing white, it's because I fear an accident while eating and getting a stain which can be traumatic.

Is it not a bit like cars where a black car is almost as difficult to keep clean as a white one? Regarding heels specifically, I do think black shoes are easier to clean whereas my limited experience with white shoe-polish has been rather disappointing. I have a pair of white leather courts that I've not worn outdoors for fear of ruining them. However I do have a pair of white patent (synthetic) peeptoes with a cork wedge heel that I'm more relaxed about wearing out and about.

I couldn't put eye makeup on in the subway, ill poke my eye out. Some women are amazing at it. I saw a women putting on fondation on with a brush, whiile driving merging in on the freeway(hwy 401 in Toronto, 8 lane). Crazy! I get all that shit done before I leave the house. Can't be in publkic without it, and 5" heels of course!

The subway is fine, but applying makeup while driving is just dangerous and irresponsible. In any case, I've not worn makeup for a couple of years, although I do cleanse, tone and moisturise. It's not that I don't find makeup fun and exciting - the first time I saw my eyes in the mirror with mascara was a comparable feeling to the first time standing up in heels. But since I started heeling in public it's been more important to me to retain a sense of "guy in heels" so I avoid wearing any makeup. Having said that I have nothing against those who do choose to wear makeup.

Nice outfit Sleek! You wear it well!

Thank you Mr. X.

[Puffer]

... I've not worn makeup for a couple of years, although I do cleanse, tone and moisturise. It's not that I don't find makeup fun and exciting - the first time I saw my eyes in the mirror with mascara was a comparable feeling to the first time standing up in heels. But since I started heeling in public it's been more important to me to retain a sense of "guy in heels" so I avoid wearing any makeup. Having said that I have nothing against those who do choose to wear makeup. ...

Correct me if I'm wrong, SleekHeels, but you appear to be wearing nail varnish on your toes in your 'wedge' pics - or don't you consider that to be 'make-up'?

I have to say that I think you look great in those pics and I really like the sandals. I wear sandals as much as possible during the summer and just wish that I could find the lighter, strappier styles (with or without heels) in large sizes. I recently wore a pale frosted pink semi-matt varnish on my toes and was pleased with the result - it was very discreet and disguised a discoloured nail (damaged a while ago) - but my wife would certainly not approve.

[SleekHeels]

Correct me if I'm wrong, SleekHeels, but you appear to be wearing nail varnish on your toes in your 'wedge' pics - or don't you consider that to be 'make-up'?

Yes, I suppose nail-varnish is makeup and I should have clarified that I avoid wearing any facial makeup. I do consider nail-varnish slightly different in that respect and I feel I can wear it and still project a "feminine guy" image.

I have to say that I think you look great in those pics and I really like the sandals. I wear sandals as much as possible during the summer and just wish that I could find the lighter, strappier styles (with or without heels) in large sizes.

Thanks for your kind words Puffer. Since I started heeling in public I've always felt more comfortable with autumn/winter fashions, so this summer's been quite a journey of discovery for me experimenting with wearing skirts and sandals in public for the first time. It's been fun and the feeling of freshness adds a whole new dimension to summer, like its been in colour for the first time instead of black-and-white.

[Curt]

I love the fall/winter fashion as well. Long coats, cardigans, tall boots over leggings, and some stylish layering. So much more to put together this time of year. I get inspiration from the women out and about. Thank god its too cold for flip-flops, as least most women. And men look worse in them. Not that I would get any inspiration from the way men dress in my area, unless I want to work for a pest-control company. Btw, I really like your stylish look. I would like to put some of that into my look, I'm too funky for my own good.

[SleekHeels]

It has been a while since I last posted here, but I certainly have been wearing my heels lots. I still mix things up, mostly wearing my heels with bootcut jeans and a shirt, but occasionally wearing a skirt or dress (just because it's fun). I've still never been called "ma'am", only "sir", so I'm pleased that I'm coming across as a fashion-adventurous guy. As I've got more confident showing off my heels with a skirt or dress, I have found that people seem to keep their distance more, whereas a more androgynous look seems to be more approachable (maybe they don't even notice the heels).

 

This week I did something unusual for me, I went out heeling with about 2-3 days beard-growth. I was wearing my brown mule sandals (4¼" heel, ¾" platform) with bootcut jeans and a shirt. I walked down the main street to donate some old clothes to a charity shop. The heels were certainly visible under the jeans (but rubber soled therefore hardly any noise) and most people didn't seem to even notice at all, just very brief glances from a couple of young women (maybe the most fashion-alert demographic group). Wearing heels with beard-growth was more outside my comfort zone than wearing a skirt, but as a guy in heels I felt I had to challenge that and be more adventurous in ways other than exploring "feminine" fashion.

 

A couple of weeks ago I wore my black suedette knee boots (3½" heel) with a camel/black geometric print midi dress and a black blazer. Also (since my last post about never wearing any facial make-up) I wore a little mascara and some natural pink lipstick, which I've started occasionally doing lately. At the busy cafe a couple of ladies asked if they could share my table, and one was quite chatty with me (just about general stuff, not a hint of reaction to how I was dressed). At one point I said to her "You can hardly have failed to notice how I'm dressed, do you mind if I ask you what you think?" and she was very sincere in saying that it surprised her a little at first but then she thought it was fabulous and if that's how I usually dress I should keep on doing so. It was really nice to hear a positive reaction.

 

That same day, as I walked through the mens toilets to a cubicle, a guy called out "You're in the gents!" (to be fair to him he didn't see my face). I should've called back "Oh, that's a relief!" but I didn't think of it in time and the moment was gone. I also seem to make a lot of guys who are entering the toilet do a u-turn and check the sign on the door,  and one time I said "It's alright, you're in the right room, I'm in the right room, I've been confusing people all day!" which he found quite amusing, and was a nice way to diffuse the awkwardness of the situation.

 

Another day at the cafe I had a friendly chat with a lady who said she'd noticed me around before, and that I usually looked unremarkable from the waist up but then I get up from the table and I'd be wearing heels, which she seemed pretty cool about. As we walked from the queue to a table carrying our coffees, she asked if I needed any help. Of course I was determined to teeter along in my heels without spilling a drop of coffee, and succeeded (well, I've surely had enough practice by now).

 

I've not been able to buy so many new heels lately, but this week I did buy a nice pair of ankle-strap sandals with a 4" heel (and no platform). I was wearing a skirt and heels while I was browsing the store, and had to ask an assistant to get my size as it wasn't on the racks. She brought my size and straight away asked if I'd like to try them on, which I did (a perfect fit) before taking them to the cash desk to buy. She smiled and was friendly throughout, and it was lovely to be treated like an ordinary customer. Most of my shopping experiences are like that. I've not posted to the "New Shoes" topic yet because I'd like to smarten up my toes and post a "selfie" photo instead of just pasting the photo from the retailer's web site.

[bluejay]

Nice post, Sleek heels. I enjoyed reading it.

 

Happy Heeling,

bluejay

[Shafted]

Great read Sleekheels!

 

Another day at the cafe I had a friendly chat with a lady who said she'd noticed me around before, and that I usually looked unremarkable from the waist up but then I get up from the table and I'd be wearing heels, which she seemed pretty cool about.

A hint maybe?

[SleekHeels]

Thanks guys.

As for the possible "hint" Shafted, I'm a guy so I tend to either see hints when they're not there, or be oblivious to them if they are there. In any case, she was almost young enough to be my daughter (and the other lady old enough ot be my mother) and it was far more enjoyable to just have an open and friendly chat with them.

[SleekHeels]

I had a day off today so I decided to go to a shopping mall. I wore my blue suedette lace-up courts and showed them off with a navy skirt and grey longline cardigan over a white tshirt. I was also carrying a smart black satchel type bag which isn't in these pictures (but is in two of the later ones).

 

 

I've had these shoes for a while, they have a 4" heel and ¼" platform and wide fit so they're pretty comfortable. I walked a fair bit up and down the mall, browsed a few shops, stopped for a coffee, and also tried on some red ballerina flats that were too cute to pass on.

 

 

I got a few glances, one smile (that I reciprocated), and I didn't overhear any comments apart from one young lady saying "oh, wow!" to her friend as I walked past a shop as they were coming out. I don't think the "wow" meant I looked amazing, but the tone of her voice didn't sound scornful, more like possible enthusiasm that someone was daring to break fashion conventions and making an ok attempt at it.

 

 

Also here are some pictures of the outfit in my previous post - my black suedette knee boots (3½" heel) with a camel/black geometric print midi dress and a black blazer.

 

 

And another outfit I wore to a cafe recently - oatmeal courts with a black biker jacket over a black floral bodycon dress.

 

 

As I've said before, it's fun to be more adventurous sometimes and I'm still "sir" in a dress or skirt. It makes it seem pretty trivial when I revert to wearing my heels with the usual jeans and shirt.

[JeffB]

Well done, SleekHeels! I thought all your outfits suited you well as you looked tasteful and stylish in everything you wore on your outings. It's as I've said on my own thread numerous times, it's important to be appropriately dressed for the surroundings you happen to be in as a freestyler, and you did splendidly, my friend. As for a favorite, I have to say it's the second ensemble with the print minidress and knee boots, quite the nice combination indeed. And yes, I couldn't agree more that life is more adventurous in a skirt!

[bluejay]

I like all your ensembles, Sleekheels.

 

As JeffB said, "Well Done !"

 

Happy Heeling,

bluejay

[skirtedvik]

I had a day off today so I decided to go to a shopping mall. I wore my blue suedette lace-up courts and showed them off with a navy skirt and grey longline cardigan over a white tshirt. I was also carrying a smart black satchel type bag which isn't in these pictures (but is in two of the later ones).

 

bluecourts1.jpgbluecourts2.jpg

 

I've had these shoes for a while, they have a 4" heel and ¼" platform and wide fit so they're pretty comfortable. I walked a fair bit up and down the mall, browsed a few shops, stopped for a coffee, and also tried on some red ballerina flats that were too cute to pass on.

 

redballerina1.jpgredballerina2.jpg

 

I got a few glances, one smile (that I reciprocated), and I didn't overhear any comments apart from one young lady saying "oh, wow!" to her friend as I walked past a shop as they were coming out. I don't think the "wow" meant I looked amazing, but the tone of her voice didn't sound scornful, more like possible enthusiasm that someone was daring to break fashion conventions and making an ok attempt at it.

 

 

Also here are some pictures of the outfit in my previous post - my black suedette knee boots (3½" heel) with a camel/black geometric print midi dress and a black blazer.

 

blackboots1.jpgblackboots2.jpg

 

And another outfit I wore to a cafe recently - oatmeal courts with a black biker jacket over a black floral bodycon dress.

 

oatmealcourts1.jpgoatmealcourts2.jpg

 

As I've said before, it's fun to be more adventurous sometimes and I'm still "sir" in a dress or skirt. It makes it seem pretty trivial when I revert to wearing my heels with the usual jeans and shirt.

Great outfits - I like all of the three  .

[SleekHeels]

So, I bought some new patent courts in red and black, I've worn both to a cafe (on different days) and even got a complement on the red ones (that's happened once before with my red suedette peeptoes, there's just something about red).

 

 

The outfit I wore with the black heels was a simple black knee-length dress and denim jacket (no photos). The outfit I wore with the red ones was a black pencil skirt, red scoop-neck top and black blazer. I was going to wear a shorter skirt but I felt that the red heels were already enough of a siren and that the longer pencil skirt would be a more stylish complement for them. I think the shoter skirt looks fine with the black heels.

 

 

I also think the red heels look great peeping out from under bootcut jeans.

 

 

Also I've recreated a couple more of my recent outfits wearing my heels with jeans and shirts.

 

 

The heels in that last outfit are wooden mules, and I can't wait for a really nice hot summer's day to wear them with the outfit below (I wore the same outfit one day last summer to an outdoor cafe, but I didn't have the shorts then so I wore a light stonewash denim mini-skirt).

 

[Shafted]

Love the outfit with the white top with jeans and the plaid shirt open with a little bit of bling. Looks awesome.

[Mr. X]

Nice new pics Sleek!  And I especially love the red heels!

[bluejay]

Nice pics, Sleekheels. Thanks for posting.

 

There's a special aura wearing red heels. I like to wear red heels too. I have several pairs in different styles and yes they are attention getters!

 

Happy Heeling,

bluejay

[JeffB]

Bravo, SH! Bravo! My favorite from your latest batch of pictures was the black jacket/red top/black skirt/black heels combo. That looks mondo stylish, so much so that I might have to copy that outfit as I'm sure I could make that work for me. Well done, my friend!

[SleekHeels]

Thanks for the comments, for sure I wouldn't feel as comfortable about expressing fashion freedom if I hadn't been inspired by you guys, so it only seems fair I should do my bit too and hopefully we're inspiring more nervous newbies to do the same.

 

Love the outfit with the white top with jeans and the plaid shirt open with a little bit of bling. Looks awesome.

 

That white top is actually a "bodysuit" and I like that it doesn't crumple around the waist like some tshirts do. I have two of those necklaces, one in silver, one in gold (£6 each). I find that accessories like that can make the difference between being seen as "a guy wearing the wrong shoes" to "a guy wearing the right shoes for that outfit" and reactions are generally more friendly.

 

 

Nice new pics Sleek!  And I especially love the red heels!

There's a special aura wearing red heels. I like to wear red heels too. I have several pairs in different styles and yes they are attention getters!

 

Yes, women seem particularly in-tune to the power of red. With the young lady who complemented my heels the other day, after a brief chat about me actually being able to walk in heels (and actually offering a little advice to her!), she said there were some shoes she was thinking of buying but was a little apprehensive because the red might be a bit too bold. I suggested that if I can walk around in my heels then she should certainly feel free to wear what she likes, which I hope she found encouraging and liberating. Maybe next time I'll find out if she bought them and they made her feel happy.

 

 

Bravo, SH! Bravo! My favorite from your latest batch of pictures was the black jacket/red top/black skirt/black heels combo. That looks mondo stylish, so much so that I might have to copy that outfit as I'm sure I could make that work for me. Well done, my friend!

 

Yes, I can imagine you pulling off that outfit with no trouble at all Jeff. My recent "red" phase (buying that red top, the red suede ballet flats and the red patent heels) was inspired by a young lady at a meeting I attended last week; she wore a pale blue shirt, smart black trousers and red ballet flats. She looked really cute, professional and aspirational, and it's certainly a look that I'll try to make work for me too. I'm copying styles I see all the time, and it is said that "immitation is the sincerest form of flattery".

[JeffB]

Yes, I can imagine you pulling off that outfit with no trouble at all Jeff. My recent "red" phase (buying that red top, the red suede ballet flats and the red patent heels) was inspired by a young lady at a meeting I attended last week; she wore a pale blue shirt, smart black trousers and red ballet flats. She looked really cute, professional and aspirational, and it's certainly a look that I'll try to make work for me too. I'm copying styles I see all the time, and it is said that "immitation is the sincerest form of flattery".

Well, I do take notes of outfits I'd like to copy from time to time, and yes, I do indeed want to experiment with what you had shown us in your latest pictures. Should be fun!

[SleekHeels]

I couldn't resist going back for the beige version of the patent courts I bought in black and red last week. I wore them and the outfit in the photo to return a library book, go to the supermarket to buy a couple of things, and sit at a cafe for a while. The librarian was very friendly and polite, I was a bit over-dressed for the supermarket so I sensed a few double-takes but I've seen similarly dressed women doing their shopping on the way home from work, a little attention is to be expected. I exchanged everyday pleasantries with the cafe staff and a couple of customers.

 

The photo's not great, it's a reflection in a tinted window taken with my phone. I wore the heels with a black skirt and blazer and a dark turqoise top, inspired by seeing a newsreader on TV wearing a similar outfit. As you can see from the second photo, I felt perfectly comfortable and safe driving in those heels too, though of course I parked the car to take the photo, and my near foot is only just touching the pedal because I moved my foot back a bit so the other shoe was visible for the photo, I wouldn't actually drive like that.

 

[Mr. X]

Sounds like you had fun Sleek.  I love the shoes!

[JeffB]

Bravo, Sleek! You really looked elegant in your outfit! And the pumps were sharp too!

[Thighmax]

Hey Sleekheels, you really look good with the skirts and dresses.  Your heels also look amazing.  I see that you really feel comfortable with your look.  I would appreciate it very much if you can tell me how you got to feel so comfortable.  I have been thinking about wearing my boots publicly for a while but find it very hard.

 

Keep it going, and send pictures.

[SleekHeels]

Thanks all. I'm really liking these shoes and glad I went back for the beige ones too, my other similarly coloured heels are all suedette so it's nice to add the patent ones to my collection. It's also nice to be wearing a style that seems quite popular, I see others wearing similar shoes. I enjoy the paradox of being different and blending in at the same time.

 

I see that you really feel comfortable with your look.  I would appreciate it very much if you can tell me how you got to feel so comfortable.  I have been thinking about wearing my boots publicly for a while but find it very hard.

 

I do feel very comfortable, but I also found it very hard at first. I don't think I'd have overcome that without the more experienced members of the forum, their advice and the self-belief they inspired. But when it comes down to it there's no substitute for personal experience, and there's no magic confidence boost, you just have to build confidence little by little each time. The hardest step is just to get the ball rolling.

 

My strategy is to wear my heels as part of an overall look I feel comfortable in and feel positive about, and choose environments that I feel comfortable and positive about too. I'd say don't wear your heels/outfits trying to look like someone else, wear them because you're trying to look like you! I feel that the sense of liberating your self-expression is a big part of gaining confidence.

 

If your boots are the ones in your avatar, I'd wear them over skinny jeans with a plain turtle-neck top and a blazer (or if you feel more apprehensive, maybe under bootcut jeans with a smart-casual jacket) and go to the cafe of a big museum or art gallery, classical music venue or even a big shopping mall or department store. Personally I do think autumn/winter outfits are easier to get started with, but you can go with jeans and a light summer shirt (and maybe court wedges rather than boots) during the summer and blend in nicely.

 

None of these are "rules" as such, it's just what worked for me, I hope there's something there that inspires what will work for you.

[JeffB]

SH is right, Thighmax, there is no magic bullet when it comes to developing confidence and one's own personal comfort level when it comes to wearing heels in public, you just have to go out and do it. There will be good days, and there will be bad days, but, speaking as one of those experienced members of the forum, the good will FAR outweigh the bad. Each time you go out, you gain experience, you learn what works and what doesn't, and you'll inevitably become more at ease with yourself in whatever setting you happen to be in. As for outfits, I can only suggest that you strive to be tasteful, to avoid standing out like the proverbial sore thumb and to blend in as so best you can with your surroundings. Bottom line, it's all about trial and error, just do the best you can and you should be fine.