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A little long term goal of mine;

Pinstripe suit with a semi flared leg teamed up with and covering (ie stealth mode - unless you want to let them show) a pair of heeled Oxfords.

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I don't like the Oxford style myself - too many reminders of 'school shoes' or old-fashioned women - but I can see that heeled Oxfords have a unisex appearance and would go well with a suit, as you suggest.   A safe bet if you stick with a fairly chunky (Cuban) heel rather than a stiletto.

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On 11/25/2018 at 9:29 AM, WalkTall said:

A little long term goal of mine;

Pinstripe suit with a semi flared leg teamed up with and covering (ie stealth mode - unless you want to let them show) a pair of heeled Oxfords.

I had such an opportunity, but the shoes didn't fit very well, sadly.

While the flared leg has some potential, the absence of any toe showing is a give-away. In fact to be truly discreet, a high heeled shoe worn by a man must be 2-3 inches longer than usual. I have some very wearable shoes (easy to wear) I could walk around in all day.  Slightly flared (bootleg) jeans or trousers, hide whatever needed hiding of the heel, bit no toe showing, draws attention. Less, is not more in this instance. I have some very nice ankle points with pointed toe, that fit very well. They are half-way toward a cowboy boot, but the absence of my foot showing, suggests I am wearing a heel, and draws attention for that reason. The appearance at floor level, is of a girl wearing high heels and just a bit of her toe showing at the bottom of her trousers. Even people not into heels, recognise that look. :(  

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6 hours ago, FastFreddy2 said:

I had such an opportunity, but the shoes didn't fit very well, sadly.

While the flared leg has some potential, the absence of any toe showing is a give-away. In fact to be truly discreet, a high heeled shoe worn by a man must be 2-3 inches longer than usual. I have some very wearable shoes (easy to wear) I could walk around in all day.  Slightly flared (bootleg) jeans or trousers, hide whatever needed hiding of the heel, bit no toe showing, draws attention. Less, is not more in this instance. I have some very nice ankle points with pointed toe, that fit very well. They are half-way toward a cowboy boot, but the absence of my foot showing, suggests I am wearing a heel, and draws attention for that reason. The appearance at floor level, is of a girl wearing high heels and just a bit of her toe showing at the bottom of her trousers. Even people not into heels, recognise that look. :(  

Good points!   My 5" MJ boots have a longish pointed toe, so even when worn with bootcut jeans (not excessively long) have enough 'projection' to pass muster.   Yes, I will be showing perhaps half of the heel when walking normally (much more when crouching or sitting) but an apparent 2.5 - 3" blocky heel on a 'man's' boot does not really scream 'cd' or 'pervert'.   Closer examination will certainly suggest I am in 'unusual' footwear, but unless one's appearance, gait or conduct is otherwise attention-getting, unlikely to attract the wrath of the world (and that of his wife, kids and dog too).   Stilettos, however, are a rather different matter; any sighting of a thin heel (regardless of height) is likely to be 'provocative', especially when the typical sound effect is present too.

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3 hours ago, Puffer said:

 Stilettos, however, are a rather different matter; any sighting of a thin heel (regardless of height) is likely to be 'provocative', especially when the typical sound effect is present too.

My findings certainly support that. I don't know if some people are 'hard-wired' to pick up the tap-tap of a stiletto, but some seem to be - including me.

 

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