SleekHeels

I can relate to a lot of that Jeff, especially the positive image and "dispelling the caricature". What I like about your style is that women could wear a lot of your outfits with self-respect -  the only reason that men (supposedly) can't wear them with self-respect too is prejudice, and that's what we're challenging, Fashion's a celebration of humanity, you just keep on celebrating Jeff, and inspiring others to do the same.

For a community that advocates fashion freedom, are we not being remarkably judgemental here?

Sure, it's a more casual outfit than I might choose to wear, but maybe it suits his build better than a more feminine style, the wedges probably also suit him better than some dainty stilettos, and he's seemingly made the effort not to be parading hairy legs around. Asides from all that, he looks totally relaxed going about his day-to-day business. I don't see the "damage to the cause" just because he's expressing himself differently to how I might.

If we're going to complain about peoples prejudice towards guys in heels, surely we need to eliminate prejudice altogether, not just simply shift the line so we can point fingers at others.

Steve, I suspect you don't need to count at all, just step right out there !

Thinking about it, there's something about counting to 3 (or 4) that seems to make it more likely to achieve the desired effect. I think counting to 2 doesn't give you enough time to commit, but counting to 5 gives you a bit too much time to dwell on it and chicken out. Maybe it's something musical, like a drummer hitting his sticks to count a song in (after that the click of the heels can take over).

mI couldn't help but notice how I got more stares wearing a long skirt than I do in a short one, most unusual to say the least, but hey, that's how things sometimes go when you're a freestyler.

The colour combination is simple and effective, I really like it, and the style is great too.

As for the stares, don't you find that they are subtly different depending on what you're wearing? I know I sometimes over-dress a little (skirt a little too short and heels a little too high, but hey, it's fun to do that sometimes) and the stares can be a little mocking/disapproving, or people just assume the clothes/shoes are just a sex thing. But a more modest outfit, such as the long skirt and wedges you wore, tends to eliminate that perceived fetish element, and people still stare but in a different way, as if they can't quite get their heads around the fact that you might actually enjoy dressing that way simply for the pleasure and style of it. I think that challenges peoples prejudices more, they can't quite dismiss their confusion by laughing it off. Also, not all stares are bad, sometimes people stare in a way that says they'd like to say something nice but they've been caught off-guard. Do you feel that variety of stares in your experience too?

... an influence from my youth which was in the early 80's when most men wore make up and gender bending clothing...

Not where I was growing up !

Regarding Newfie's look, it's certainly not what I imagined when I saw just the shoes, but it totally works and looks very natural. Well done sir !

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".

# "Oh, what a feeling... When we're dancing on the ceiling."

I was parked at their front door with my black Jasmine's in place ----- and never got out of the car.  I feel like a "dumb cluck."  The storelooked empty. Maybe next time I break the "sound" barrier.

Don't be too hard on yourself, it is a hugely intimidating step to take.... until you actually do it and only then do you realise how easy it is. It's easy to trap yourself in the car waiting for some impossibly perfect moment to step out. I found that telling myself "I'm going to count to 3 and get out of the car" and then doing exactly that helps to kick-start it, and everything kind of flows after that.

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).

Just when I thought I didn't have space for any more shoes, I found these at Primark. I tried them on in store, they looked/felt good and I was really missing some elegant red and black patent courts from my collection, so for £12 per pair I couldn't resist. (They come in beige patent too, but I had to prioritise).

They have a 5½" heel with 1¼" platform, I saw some UK8's on the shelves but I didn't see anything larger than that. I'm a UK7 and found the sizing/fit good.

I like that panelled pencil skirt style, us guys are usually too slim in the hips compared to our shoulders, but this kind of skirt maybe breaks up the vertical lines and re-balances things. It looks well-proportioned on you Lime15, and the length of the skirt suits the height and style of the heels.

Personally I think the black tights (which appear kind of grey/silvery in the pictures, almost like a black & white photo) look a bit wintery and could work well with a grey blazer (with the black shirt and one of your famous ties in blue, or perhaps a blue shirt and no tie). For the more summery look with the short-sleeve shirt, I wonder if maybe sheer tan tights would match nicer with your arms, or if your legs are tanned then bare legs would look great too (and would avoid the zip detailing on the shoes snagging your tights as you mentioned in your other post).

It's nice to hear that you wore your heels out and about and seemed to enjoy the experience. Getting some of your boldness back indeed.

When the sales lady asked what the occasion was ... my wife blurts out I can't have him walking around in pumps all winter. The sales lady smiled and said try them on and see how they fit .

That's very cool of your wife to do that (Nice boots too).

Immortal

Perhaps. I just how people like to laugh at others or make fun of others because it makes them feel better about themselves.

And the people who give compliments feel better about themselves too

These are my new ankle-strap sandals (from New Look). I thought the heels looked a little low when I first saw them, but they are just about 4" high, and when I tried them on I rather liked the heel-height as it is, even though they don't feel too steep and I could comfortably wear a little higher. For sure I wouldn't want them any lower.

In the end I liked them so much I went back and bought a second colour - the black ones a synthetic leather-like material (and also come in a bright coral colour), the oatmeal ones are suedette. I'm thinking they'll look good with cropped skinny jeans (or a skirt/dress), it'd be a shame to hide them under bootcut jeans.

Thanks for the kind words, Mr. X. Ever since I fully devoted myself to being a fashion freestyler, my objective was to look my very best in clothes worn by the opposite sex. I want to put the idea in people's heads that a guy can look just as normal in a skirt as any woman, and I think I'm getting closer to that goal all the time.

I can relate to that Jeff. We're still a tiny minority and many people find it easier to react in a very conditioned way, but I think we do press people's "challenge preconceptions" button - whether that button is wired up to anything or not depends on the person, but I think more people than we realise do respond in an intelligent, open-minded way even if they don't show it.

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.

Are these shoes to loud ? I can't decide. The other day when I was wearing them out shopping, it was only the second time outside since I bought them 4 years again. No reactions to speak of, but I'm not sure. The thing is that their very comfortable.

I think those shoes look great and fun to wear. I don't think they're too loud, but they could easily become part of an outfit that's too loud. However, you've chosen to make a feature of the shoes with a casual look and I think that works. As for the jeans, I love bootcut jeans but in my opinion the straight-leg you've worn (or even skinny jeans) suits those shoes better. The neutral plain grey tshirt you're wearing helps to make the shoes the highlight without being too loud because it's not competing with the shoes. You could also try a tshirt matching the darker colour on the shoes, which would make a slightly stronger connection with the shoes without drastically changing the overall style that you're comfortable with.

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.

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.

I have a small plot where I grow beans, carrots, beetroot and onions with reasonable success. Also tomatoes and peppers that are a bit more variable depending on if we get a decent summer or not. A few pots of herbs too (parsley, corriander and mint), and I'll usually plant a couple of tubs of flowers each summer. I don't have a greenhouse to grow my own seedlings, but I do have a small compost bin so no organic scraps go to waste.

One thing I have noticed gardening in London is a lot of pests, presumably they stick around while the urban surroundings scare off their predators. The slugs are terrible so hedgehogs would be welcome but I've not seen one in years. Also local council parking policies have encouraged lots of people to pave their front gardens into driveways, so all the birds that used to nest in the hedges seem to have disappeared. I also remember seeing so many ladybirds when I was a kid, but it's so rare to see one now (unlike all the little flies they used to eat which are everywhere now). Is pest control any easier for you guys in rural areas?

Sustained

How about when wearing sheer tights with a skirt and crossing your legs? Buckles on the inside would shred those tights pretty quick !

They do have a slightly "cone heel" appearance. My heel-shape sweet spot would be thinner than that with a nice tapered shape, but not pencil thin (they can look nice on others but they don't suit my build). Having said that I really like some chunkier heels shapes and wedges too, so it's not just about thick/thin for me, some very subtle changes in heel shape can make all difference.

I don't find it at all frustrating, maybe I've just got used to it. Also, for those who choose to wear skirts with their heels it's much easier to fasten an ankle strap on the outside (with knees together) rather than inside (knees apart) while maintaining some degree of decorum