pebblesf

Same here. So many years wasted with self doubt. I guess one benefit of my advancing age is that I am much less affected by "what others might think". For the most part, I think I look great in boots and jeans. "Too little too late" I guess, but that is OK. I punished my young self so severely, such a waste. My life would be complete if I could help at least one guy get over these silly "social norms" that seem to have a strangle hold on us.

Don't do that to yourself. You have taken good care of yourself and look better than many younger folks. So sorry the wife isn't a bit more supportive, I have similar issues with my better half.

Tough to remember, because i progressed gradually. All started with 2" block heeled Frye Campus boots and cowboy boots, always looking for cowboy boots with taller heels. I made many thrift store purchases also. My first actual purchase was online, a few pairs of Pleaser boots.

Precisely. Regular guys wearing nice boots and outfits that isn't some crazy over the top design for the runway. But, I guess our "carpet" is our day to day travels going about our lives in public.

Now these look great and fit nicely

So true, I always know the brand name of my boots, sometime the model name as well. But, good luck finding them...

For sure. Furthermore, these boots and outfit were probably just grabbed "off the shelf" and given to the model to wear, no time for custom fitting, etc.

They are nice boots, but sure don't fit his legs very well. The important thing is that he is wearing them, perhaps helping to normalize guys wearing great boots

OK, so the guy that "gave you the once over" was the same guy at the counter, correct? When you say "once over", did you feel it was a positive once over? Any curiosity as to how the conversation would have gone had it occurred? I have reacted the same way when encountering fellow crewmembers on a layover.

Those boots are amazing

Well yes, it all began for me when I was just a kid and totally mesmerized by my sister's red go go boots! Couldn't wait to be left home alone so I could wear them. Would still like to find a pair in white or red!

For sure! For me, it was a gradual process I guess. Always loved cowboy boots, then progressed to higher heeled cowboy boots. Then I looked for higher heeled "cowgirl" boots. I'm trying to remember the first time I actually ordered boots with stiletto style heels, I think they were Pleasers. The progression to wearing high heel boots in public was a slow gradual process as well. So much regret wasting so many years of enjoyment due to self doubt, and lack of confidence...

So sorry you didn't have these great boots for your trip! You would have enjoyed many miles of fashionable/comfortable walking trips for sure

Well, I would like to think that I "finally came out OK". Unfortunately, I wasted so many of my younger years with self loathing/doubt/insecurity. One of the only advantages of advanced age is that I finally "don't give a crap" about what others think, for the most part. I think I look good in my boots, which is the most important thing....

Yes, I'm sure immature teen age boys will always be an issue. What an awful age... Wish I could repeat my teenage years, and do it right...