Unhiding my heels

[pebblesf]

20 hours ago, hiddenheels said:

Oops, went Christmas shopping and forgot to hide my heels!

 

[it's a skirt]

 

Was wondering around the plaza for about 3 hours. No one said a word, although I saw some people do double-takes. Heels are 4.5".

You look great buddy!  The boots fit perfectly and the outfit looks great as well!  I'm sure there were some second looks indeed, consider that a big compliment!

[Shyheels]

I remember the first time I forgot to hide my heels and answered the door to our post lady while wearing my stiletto knee boots. 

[Puffer]

4 hours ago, Shyheels said:

I remember the first time I forgot to hide my heels and answered the door to our post lady while wearing my stiletto knee boots. 

I'm sure you exhibited a First Class Male appearance!

[Shyheels]

It was a special delivery 

[hiddenheels]

Hi!

I have no clue where the days/months/years are flying by. Have been heeling pretty regularly (usually weekly, sometimes twice), and have gotten comfortable, in both the emotional and physical sense. Emotionally I get much less worked up, or none at all, when wearing heels, no more anxiety and just get to enjoy it. Yes, it takes mental effort to plan out which cloths I will wear so things match, but otherwise I'm good. Physically am getting better at wearing 5" stiletto pumps for 2-3 hours walking around. 5" boots no problem.

 

Recently saw this boot (in the picture below) and I reeeeally wanted it, they were gorgeous, and I loved the color. $180, and given the number of shoes I have, it's not something that made any sense, so I talked myself out of it. However, a week back, I noticed they were on sale for $70, and upon impulse, walked into the store and asked if they have it in my size. I was doubtful, but the lady brought it out. Took off my 5" boots, and tried these on. They fit perfectly, loved the whole thing, and couldn't resist. YOLO and all that. Few days ago, had a chance to go shopping, and wanted to show off the boots a bit. A bit of chat with AI helped me figure out some color combinations that would style the red well (AI hopefully gave good tips, my style sense sucks, so it can only get better). Ended up with what is in the photo, with a white TV shirt and grey hoodie on top. Obvious I'm a guy, have good facial hair. Felt comfortable. Went to a diner for food, then spent about 3h shopping, book stores and such. Two ladies complimented the boots. I'm sure others looked, but it was comfortable. 

 

Guess my unhiding is progressing. 

 

Wish family was supportive, but this still is a lone exercise.

[Shyheels]

Those are very nice boots! And you wear them well. That’s a nice combination. I’m very much a boots-and-jeans guy.

Forget AI. No one needs it. Trust your judgement. After all it was your inner voice that led you to heels in the first place, not the promptings of a computer, so you can’t be too far wrong can you? 

[pebblesf]

Those boots are amazing, my favorite classic style, love the color.  Looks like good quality leather as well, you look great!

[mlroseplant]

Those are certainly loud and proud. I approve!

[pebblesf]

4 hours ago, mlroseplant said:

Those are certainly loud and proud. I approve!

For sure, my favorite "classic styling", they fit his legs so well, love the color, they look great over the jeans.   So envious!

[higherheels]

A great pair of boots!

And the red for sure screams "unhiding", so you did well 😉

[hiddenheels]

On 2/13/2026 at 2:11 PM, Shyheels said:

Those are very nice boots! And you wear them well. That’s a nice combination. I’m very much a boots-and-jeans guy.

Forget AI. No one needs it. Trust your judgement. After all it was your inner voice that led you to heels in the first place, not the promptings of a computer, so you can’t be too far wrong can you? 

The discussion with AI was more around color-choices, styles, etc. "given I'm a guy and wearing red knee-high boots, how should I style it". It gave me some good ideas, after which I put together what I wanted. It's great for generating ideas that I might not have thought of it, but the final decision is of course mine. The heels, I'm actually very happy that I'm getting comfortable with them, no more guilt, and enjoying things. It's good to be different.

 

On 2/14/2026 at 2:47 AM, mlroseplant said:

Those are certainly loud and proud. I approve!

This is where AI helped with styling. I had 0 ideas on how to wear something so obvious and colorful! Told me "hoodie", I'm like WHAT? Hoodie with elegant red boots? But some google image searches showed women wearing hoodies with boots and they looked fantastic, so why not? This is why I appreciated AI, gave me an out-of-my-box idea. 

 

Much appreciate the support everyone! Will try to post more often.