What to wear?

[platformman]

Hello everyone,

I joined this forum a few years ago, but never posted anything.

I've been wearing heels on and off in public over the last 15 years or so, and its always been boots with otherwise what would be considered to be "mens clothes". I've mainly worn block heels, and on a few occasions i've worn stilettos. Reflecting on it lately, I realised that I really love wearing a high stiletto heel, and that I now want to do it more. It's the total package, the look, the thinness of the heel and the intoxicating sound of them clicking when walking! I've just bought a pair of these on eBay (1969 italia boutique) and waiting on them being delivered:

 

I personally think they are utterly gorgeous, but they are very extreme boots in terms of heel height (17cm) and in length. They are my first pair of crotch boots and it does lead me to think, what the hell do I wear with them? I don't want to go down the road of wearing a dress or a skirt, so I was thinking on either skinny jeans with a nice shirt and a leather coat, or a long wooly jumper (almost would qualify as a dress when you think about it, go figure!) with plain or leather leggings. The boots are so long that I suspect the jumper will cover the tops of the boots. I am of the mind that I want to "show them off", as I don't want to make any attempt to conceal that I am wearing a pair of sky high heels. 

I'd be interested to hear what anybody thinks, or can provide advice from similar experiences.

Thanks

[MackyHeels]

Glad you enjoy your new purchase.

Although i'm not experienced to comment as other heelers i can add my opinion.

As for your wooly sweater idea i believe that would be a mistake. Only that the slick thigh boots don't compliment a sweater style mode, maybe for a suede knee high boots yes.

You bought these boots needs to be complemented with slick fabric or coated skinny jeans or leggings, maybe latex if your so bold. Leather leggings maybe an option but i think the boot material might clash with any sort of plain denim. Other option is some thick tights in some pattern but opaque as you can find no sheerness showing. 

You stated not wanting to wear a short mini skirt, think it goes really well with the outfit. Again if your not comfortable wearing it might try a fitted tunic jersey  fitted tightly along the thighs maybe some elasticity along the hem. So in reality your wearing a dress anyway.

Leather black short shorts may work also.

Again your wearing boots that are extreme and a style begging to be noticed. So wearing a short skirt with pantyhose wouldn't look that shocking only compliments the boots. You can try to look unstated with the rest of your outfit but to my eye it would look odd. Only compliment i may give someone wearing how you describe your choice of accessorizing is nice boots but leaving it as conflict to the appearance. 

Maybe i'm confusing you on my suggestions but i can explain it with analogy better. Would you think if someone wore casual ski wear jacket, ski wear bulky pants, then had on some patent loafer dress shoes on. Would that conflict with the outfit? 

So by your admission trying to tone down your attire maybe wrong decision only because the boots demand complimentary clothing.

You can try buying some asymmetrical sweater that goes high low almost a poncho style which is very trendy. Just have to be careful of the materials look too dull.  

Or go with a FROCK that might be your answer and compromise with some spandex female yoga seamless short shorts underneath.

Silky Blazer jacket with a latex catsuit black with some short white shirt maybe silky sheer. 

[platformman]

Thanks for your advice. Maybe you are right, I should just go with wearing a shortish skirt (i like skirts, just never really considered actively wearing them) given the extremeness of the boots! I also quite like the poncho idea, which combined with leather leggings, could be quite a killer look.

[CAT]

Those boots absolutly need to be seen!!! I would pair them wth the shortest leather mini skirt I own. Several of my past outfits are thigh high boots with mini skirts in my albums. the leggings or skinnys would  look better with knee boots or thigh boots. Those are higher then thigh high and are awesome. I have said before wear what you want don't wait like I did who cares what people think.  I have only been wtf'ed a couple of times. Everyone else has been positive and at the very least been intrigued to start a conversation about a straight guy in heels and a skirt and not trying to look or pass as a girl. Have fun before its to late and your to old!!!

[MackyHeels]

5 hours ago, platformman said:

Thanks for your advice. Maybe you are right, I should just go with wearing a shortish skirt (i like skirts, just never really considered actively wearing them) given the extremeness of the boots! I also quite like the poncho idea, which combined with leather leggings, could be quite a killer look.

Wearing a skirt isn't going to shock people as much as looking at the boots. In fact our minds are conditioned seeing woman in mini skirts wearing such boots.

 

Much like you i don't wear skirts or a dress i hesitate to even contemplate actually owning one. Never thought to wear one until i seen some pictures of our heel members wearing it without consequence and in truth only piece of clothes that can work wonders with certain outfits.

Came to realize, if i find my perfect stiletto heel booties or heel boots, like you showed in the picture, would people think those are male shoes and not give me a second look, ignoring me? Of course not. They immediately think he is wearing woman shoes, block heel or stiletto no difference he must be a drag queen, crossdresser. Even if i paired it with leggings or jeggings which are female by the way, won't change "their" attitude or opinion what i'm wearing, even if it's a mini tight skirt. Now if you decide wearing the wrong item say a ruffle pleated skirt, or loose curved hem dress it may take away from the style your aiming for. You maybe at  odds and funny style even if a woman wore exactly the same.

Last thing we want is some woman staring at us wearing whatever and say to her friend, even a woman wearing that looks stupid and awful, all awhile laughing upon your edgy style. 

My opinion attire or copy what a woman would wear and do it right, then anyone seeing you will only have to say, he done good regardless if they agree with your cross gender wearing costume. People who hate seeing you in heels let alone in a tight mini skirt and tights will ignore your existence. Why pander to the haters trying to look masculine wearing baggy shirt and blue denim loose jeans. People will find it more amusing thinking this guy must be drunk stealing a woman's heel boots dressed as a male. Same as a male going out in pajamas and slippers in the middle of the night. When taking effort required to select the right accessories planed in advance shows that you care about the style of boots and clothes complimenting it also. While others will see the positive picking out certain piece you be wearing, be it printed tights, leather leggings, skirt, Poncho, jacket etc... 

Keeping it simple with little anxiety is find short i mean short jacket like picture below. Find thong black leotard to wear as your base under the coat. Then wear some leather like J-brand 485 slick material, super skinny jeans lux sateen. Save the cash wearing leather leggings use it to buy the scuba skirt or leather fitted one.

Another option is same as the torso  i stated above but wear shiny spandex burgundy leggings maybe without a short jacket but a silky fitted blazer. You need to protect your legs in case of chafing occurs from the boots.

Also where are you going to be wearing the boots?

If you wear them to night club on a Saturday night what mode of style are you going for? Fetish, latex with whips sex club, after hours. Costume fashion post awards party? 

Do feel some heels are for certain functions and modes. Problem you may have is being overly dressed. Happens to people and often seeing smirks finding it silly and uncomfortable for that particular person wearing it.

Are you going to be wearing those boots in church with all seriousness? 

Often i just don't think what outfit can i wear these boots with. Asking myself where can i wear those boots when i'm considering purchasing XYZ ? 

 

[Thighbootguy]

6 hours ago, CAT said:

Have fun before its to late and your to old!!!

Hey, it's also fun when your old too.

The boots look great but I'm not a fan of platforms.  I suggest trying them with skinny jeans as regular jeans would be lumpy under the boots and a short leather jacket.  However, if you have @CAT's nerve a mini skirt or short shorts with hose and a short leather jacket is the way to go.

[robbiehhw]

Leggings would work for those as well. I'd likely go with an extra long top that looks like a dress but is long enough and maybe shorts for modesty underneath. The latter could involve tights too.

[HappyinHeels]

platformman,

Having worn mostly block heels and occasionally stiletto heels I wonder if you fully appreciate the leap you have taken. Don't know what the highest heel you wore before but now you've got a boot with a 6.5" heel and wonder what to wear. This type of boot cannot blend into the background as you will be noticed. Unless you're about to strut in NYC, or Paris, or perhaps San Francisco you can expect plenty of looks because it is a thigh-high boot with a sky-high heel. I would not hesitate to wear a sweater dress or skirt of some type. You've already invested in a very feminine-looking pair of boots so why not logically complete the outfit. Thighbootguy is the expert on this as he is the one who has been wearing thigh-high boots regularly in northern Kentucky, wears a beard, and is an older guy and none of this phases him. Look at the sheer number of view on his thread as it higher than many small cities in the US so many are interested in his advice and stories. I also like higher (5" and higher) and wear them anywhere I can and nearly every day. My advice to you is simple: You've already stepped out the door with your purchase. Complete the outfit, keep your head high, eyes level,  and go for a stroll!   I would wear the outfit perhaps to a club or something like that.  HappyinHeels

[freestyle75]

Hi Platformman,

I am probably going to get a lot of negative feedback on what I am going to write, but you asked for the honest opinions of everyone.

Honestly, I do think that any thigh high boot (also worn by a female) poses the risk of coming across as someone from the red-light district, depending on 1) the boot and 2) what you combine with it. Another thing that I've read somewhere is that if you go for a thigh high boot, it should be very high quality, as it would otherwise come across as being "cheap", with both meanings of the word fully intended. Then there are recommendations to be cautious about the heel height and type. Not going too high, not choosing a stiletto, but maybe a block heel, not going for a platform... quite a long list of things that people come up with in order to avoid any negative associations with the overknee / thigh high boots.

I totally like the shape of the boots you have chosen. I like the shape of the platform, and the balance between the stiletto heel height and the platform itself. Then again, the boots scream to me that they are made from "manmade" materials, as they call it - some plasticy stretchy material. The stiletto heel is sky high, the material looks cheap. These are boots that will cause lots of attention. They are also boots that you can combine with whatever "innocent" piece of clothing you have (e.g. heavy knit sweater) - they will always look too much fetish-like for any bypasser.

Look at "15 ways to wear thigh high boots this winter" or "How To Wear Over-The-Knee Boots Without Looking Totally Tacky" - there is hardly any girl in these pics wearing boots like these for an everyday situation.

In my opinion, the only opinion that fits to these boots is that IF you wear them on the street, you can also put on a miniskirt and all the things you always wanted to wear, but were afraid to do so. With those boots, it doesn't matter, because everyone will be looking at these boots anyway.

If I was in your situation, my question with those boots wouldn't be what I wear with them, but rather where I wear them. Recreational home use? Ok. Going to a fetish party with lots of girls that wear similar boots? Check. Doing my Saturday errands or buying stuff in the supermarket?  not so much.

I don't mean to diminish the joy you are getting from buying/wearing those boots, but be a little more self-aware as to what situations are the right ones to wear them in. If I want to make people accept me in heels, I need to wear stuff that also women would wear in a similar situation. Just my two cents.

 

[CAT]

I can agree with some of what was said. However the boots and the outfits that I have worn out that are in my albums have never once had any negative comments.  Actually the girls that have literally stopped me have asked where I bought them, what brand they are, as well as being told you so rock those boots. Never once asked if I was working the street !!!   Also agree that you need to spend some money on nice boots.  People can tell a 49 dollar pair of boots as opposed to a 200 pair.  

[MackyHeels]

I can agree with some of what was said. However the boots and the outfits that I have worn out that are in my albums have never once had any negative comments.  Actually the girls that have literally stopped me have asked where I bought them, what brand they are, as well as being told you so rock those boots. Never once asked if I was working the street !!!   Also agree that you need to spend some money on nice boots.  People can tell a 49 dollar pair of boots as opposed to a 200 pair.  

 

 

The theme of the replies tend to lead to wear your clothes appropriately with acknowledgement that your boots send a effective message by themselves. Trying to tone down your style yet wearing said boots can be fashion style mistake.

  Often woman wanting to wear outfits that are sexy but once they look in the mirror, rethinking the attire. Before going out the front door begin to change into more conservative clothes or what they view  toning it down. Often they making a big mistake only reason they do it because of fear what someone might label you as ie; slut, hooker, pornstar etc..

In my observation seeing many times woman hesitate or incomplete outfits looking very odd style of her original motivation. Woman wears killer platform 5" heels glossy fishnet pantyhose originally paired it with short scuba dress or leather mini dress. Then suddenly change their minds and put on a pair of knit black loose pleated shorts thinking it shows my legs and thighs all the same as a leather mini, how wrong and silly they begin to look.  Or change their pantyhose from fishnets, glossy nylons to matte black cotton or ordinary opaque  thick leggings.

Do agree owning up to your clothing,  shoes, cost $$$ and informed people know it often envy starts or jealousy. Those who don't know the difference between Prada shoes or Jessica Simpson booties often look closer and longer attracted to the expensive designer labels. Don't believe you have to live by that rule of buying designer clothes sometimes a medium brand balances out the huge markup versus quality fabric materials with exact same style that can compliment many things.

Only thing i know from experience is models that are in the know of designer circles, observing brands sometimes don't care. It's about how something looks fabric, color style outweigh the designer label. Yet people who try designer clothing, shoes and compare their low end affordable uncomfortable attire notice the difference. 

Do see a notable difference with demeanours from the ladies who are fashionistas seeing me in designer brands and acknowledge it directly or to someone else with regards to my specific clothes or shoes. No difference if wearing male gender clothing or female gender clothing on a man woman in particular will glance seeing what your wearing. Either they see your happy and express compliment or look away thinking he looks so cheap or tacky. 

Again it all depends on person's taste some enjoy wearing conservative clothing ie, Cindy Crawford style. While others enjoy a more racy style pushing the fashion limits ie, Jen Lopez or Nicki Minaj. One doesn't wear the other style clothes vise versa. Doesn't mean one style is better than the other. Only thing that matters is feeling comfortable wearing what you do. Not caring what people will say about you only when it's a compliment then voice your opinions otherwise we don't want to hear it.