Why the stigma for men?

I have a lot of color in my closet. Lavender, shades of orange, coral, pinks, light blues, quirky prints. They allow me a way to express, while still dressing “normal”.

The funny thing is, that when I wear such colors, it’s women who complement me the most. Straight guys, go get some pastel, or funky printed shirts, then let the women come to you.
 
I refuse to wear ties and not just because I can’t tie one properly. Someone asks me why and I will gladly chew them out about how idiotic it is to voluntarily put a noose around your neck. I may not get in fights that often, but that doesn’t mean I want to set myself up for an easy defeat in one. I’m not suffering serious heat days (we have quite a few of them every year where I live) wearing long sleeves for the sake of someone else’s idea of propriety either. I know a woman who feels similarly about high heels. She refuses to compromise her comfort for someone else’s standards. Never would have gotten a job as a stripper if they didn’t allow shoes with better support than one might expect. Heh.

Not everyone appreciates such standards, of course.
I remember back when I was still working, we bought a company with five offices in TX. The first time I went there to acclimate their salespeople with our product line I wore a dark suit, which is typical in NYC. It may not have been August, but it was hot as hell and I was dying of the heat!
Around 10:00 AM we made our first sales call and the business owner was insistent... he "don't do business with a man dressed in a suit!"
I removed my tie and jacket, top few buttons of my dress shirt, and we wrote a deal worth half a million dollars!

I never wore a suit in Texas again!

There was a famous place around Phoenix where if you had a tie on, they would cut it in half and staple it to the wall!!! I forget the name, but I am sure some of you folks have heard of it!
 
Cowboy boots hold your feet tightly and help shape your calves nicely ... and they are easier to walk in than women's heels.

I wear what is comfortable. I wear for me -- not to show off. I confess that with numbness in my feet (diabetes) I usually anymore just wear something I can slip on.

I also love running shoes. They hold your feet as tightly as you wish to tighten the shoestrings. I've never owned hiking boots, but it is my understanding that they can be laced up pretty tight too.

As to woman's heals, have you ever noticed that women don't wear heals as much as they use to, and especially when they want to get things done? You don't see women (or girls) in a rec center wearing such. You don't see senior aged women wearing them at all.

Years ago a lady who used to frequently cut my hair, talked about teen girls getting ready for a prom. Her girl and her girl's friends were all weirded out about putting on nylons and high heals because it was so foreign to them. Most of the time they just wore blue jeans.

Something funny just popped in my head... Imagine if cheerleaders wore heals. I doubt with such a configuration they would win any cheerleading competition with such.
 
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I do this when dressing gender expected in public. I noted after reading your post that I have a lot of pastel shirts in my closet. Lavender, shades of pink, coral, light blue, purple. I never realized how many I’ve collected, and will usually grab one of those first. Never a snide look or even a comment, unless it’s a compliment from a woman telling me she wishes her husband would wear that color.
I have the same taste in pastels, and have experienced the same thing from women's comments! My male dermatologist commented on the coral color panties I was wearing a few years back.
 
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