Short, fat, middle aged men

[maninboots]

I’m about 5’4” tall and around 14 1/2 stone and 55 yrs old, i wear high heeled boots from ankle to thigh high and every length in between but only with jeans or trousers either under or over them, do you think it would be possible for someone of my less than perfect shape to wear a skirt or dress, i don’t want to do the whole transformation thing, only want to keep the male identity but was wondering if it could be done, i did think about trying a denim skirt or maybe one of those dungaree type dresses, I’m from the midlands in the uk if helps with your advice, I’m comfortable with showing off my high heeled boots but not sure if this would be a step too far, maybe a full transformation would be the best option, i welcome your thoughts, thanks 

[jeremy1986]

@maninboots - do you mean wear out, or inside?

if inside, sure why not?

If outside - well, I guess it depends on how comfortable you feel  in "semi mode". if you feel you can hack it - do it! 

[maninboots]

2 minutes ago, jeremy1986 said:

@maninboots - do you mean wear out, or inside?

if inside, sure why not?

If outside - well, I guess it depends on how comfortable you feel  in "semi mode". if you feel you can hack it - do it! 

Yes, sorry, should have stated that, i do wear my boots outside on full show

[jeremy1986]

1 minute ago, maninboots said:

Yes, sorry, should have stated that, i do wear my boots outside on full show

that's great - good for you.

So you are interested in taking it further?  do it in small steps (ha ha) - maybe a drive first, then a short walk in the evening in a long skirt etc...

enjoy and keep us posted!

[Lime15]

Since you already heel on a regular basis, you're already past where the biggest hiccup usually is - clomping around inexperienced and uncomfortable in heels.

The only advice I can give is the same I do to everyone who steps out in something that may be a little more eye-catching - Make sure you're clean, well-groomed, your clothes fit appropriately, and actually have something to do where you're going.  Looking put together and with purpose, even when wearing something that may be considered outside of the norm, makes it the norm.  Doesn't matter your age, physical stature, any of that - that's why we wear clothes.

I think a lot of us that live in larger cities have seen the stumbling crossdresser who looks a mess, mugging around for attention.  I'm sure all of us have seen someone on this very forum we've wanted to facepalm over.  Everyone is free to do whatever they want, you and I should have no bearing on that, but obviously it's still important to gel - even just a tiny bit - with society.  Otherwise you may as well live in a cave somewhere, and I'd assume it's hard to get shoes delivered to such accommodations.

That doesn't necessarily only apply to clothing from the other side of the aisle, any time someone is wearing an alt fashion or something that isn't frequently seen in a region.  I don't go out wearing black and blue leopard multi strap high-tops and a pop art hoodie without making sure my facial hair is well-groomed and that I'm well put together - and that's all men's clothing - but it can draw attention from some people.  When that attention is drawn I want to leave a good impression.

[HappyinHeels]

maninboots,

I think at the age of 55 you have probably earned the right to dress as you like. It violates no statute in the U.K. or anywhere else in the E.U. The sooner you dress as you like the sooner you can start enjoying what remains of your life and do so on your terms and not on those of invisible and irrelevant passersby or know-it-alls who drink away their wages in taverns. Look what women do. Change their hair, nail colour, makeup, dress like a guy, dress like a girl and nobody cares. The fun begins when you remove the mental obstacle you have placed in front of you. JeffB is a perfect example of this. He is staking his place in the world and facing that world on his terms. The virtue which allows this is confidence and the world respects confidence. Generally I have seen in this forum when someone stands in front of mirror and genuinely likes what he sees then he will be confident to walk out the door and present that same image to the world. Think of it that way. Some here only wear the heels while others may blend some feminine and masculine items together while others will occasionally go out fully dressed en femme. It depends on what personality they want to present. Many here have received very positive comments. If someone is silly enough to say something stupid then they are likely to get stepped on sooner or later. Confident people always look like they belong and know where they are going. That's where I think we all strive to be. You'll figure this out. HappyinHeels 

[Bubba136]

Well spoke.  Jeff B is a classic example/model.

[HappyinHeels]

Yep. JeffB has higher relevant viewership than some networks masquerading as news outlets. An audience many an aspiring stand-up comedian would envy. And his Eagles won last night so he's a happy  example/model   HappyinHeels

[JeffB]

3 hours ago, HappyinHeels said:

Yep. JeffB has higher relevant viewership than some networks masquerading as news outlets. An audience many an aspiring stand-up comedian would envy. And his Eagles won last night so he's a happy  example/model   HappyinHeels

Damn straight! I am a happy camper after a big win by my Birds! 

maninboots: As the others here have already stated, WEAR what you want in the WAY you want and GO where you want. The important thing is to be confident in how you present yourself when out in public, behave like you belong in whatever environment you happen to be in, because you DO belong! Never, and I repeat, NEVER think any other way!

[CAT]

45 minutes ago, JeffB said:

Damn straight! I am a happy camper after a big win by my Birds! 

maninboots: As the others here have already stated, WEAR what you want in the WAY you want and GO where you want. The important thing is to be confident in how you present yourself when out in public, behave like you belong in whatever environment you happen to be in, because you DO belong! Never, and I repeat, NEVER think any other way!

Absolutely agreed with everything you said  Jeff!!!!

[Puffer]

On 9/6/2018 at 1:52 PM, maninboots said:

I’m about 5’4” tall and around 14 1/2 stone and 55 yrs old, i wear high heeled boots from ankle to thigh high and every length in between but only with jeans or trousers either under or over them, do you think it would be possible for someone of my less than perfect shape to wear a skirt or dress, ...

Difficult to say without seeing you as you would currently venture out in heeled boots.   Your weight/build may be an issue.   Could you post some pics of you as 'dressed' (your face obscured if you wish) so we can better judge?   As you are not tall, wearing heels probably helps rather than hinders your overall 'acceptability' in public, but what reactions do you get? 

[maninboots]

1 hour ago, Puffer said:

Difficult to say without seeing you as you would currently venture out in heeled boots.   Your weight/build may be an issue.   Could you post some pics of you as 'dressed' (your face obscured if you wish) so we can better judge?   As you are not tall, wearing heels probably helps rather than hinders your overall 'acceptability' in public, but what reactions do you get? 

To be honest Puffer i either get no reaction or good reaction, very rarely anything negative, I’m only a size 5 so my boots do look quite natural on my feet