pebblesf

Hoping the flight went alright, wish I was there to meet you!

You look amazing! Sure wish you were on one of my AA flights, but am guessing you were on SWA. Hoping the leather softener helped, it is so frustrating to have a great pair of boots that end up being too tight. Your feet tend to swell a bit on the plane, so you must have been suffering. I hate it too! Only a few more months before retiring from AA.

You look amazing, what a great outfit

I have finally reached the point where I go out of my way to compliment another person that I see wearing great boots. A few years back, I was having a drink in a bar watching folks go by on the sidewalk. Suddenly I saw a tall young fellow strolling by with his friends wearing some nice tall heeled ankle boots. I decided to step outside quickly to compliment him. Like I said, the fellow was tall so his stride was much greater than mine, really had to book it if I had any hope of catching up to him. I turned the corner on the next block to find him waiting in line to another bar. I stopped briefly to compliment him. Being older, I am very aware of my possible "creep factor", so want to avoid that with young people. The young man thanked me and I moved on. Even though the encounter was brief, I was happy I made the effort.

Cool! Always looking for new bootbuds to hang with!

Beautiful boots, great for any occasion or excursion... Very intriguing indeed. Love the straps, the color, the great heels and toe shape

So you are much closer to STL? Occasionally layover there as well. D

Richard- I just want to compliment you on accomplishing more in one year than I have accomplished in over ten years. You really look great buddy. I too, love to talk heels with other guys/gals. And, it is just how you put it: "it takes plenty of courage and confidence to wear outfits that other guys only dream of secretly". You have taken good care of your body and look great in all your outfits, you deserve the pleasure of wearing them for the rest of the world to enjoy, if they want to. If they don't, who cares! I can honestly say, that I have reached that same level of confidence while wearing my boots. I know that other guys do notice, and are envious, even though they would never admit it. I used to be somewhat of "a deer in the headlights" when I would get the rare compliment, but now I take the time to thank whoever it is and continue the conversation if they want to. You are so fortunate that has a loving wife that is secure in your relationship and wants you to be happy. Take special care of her for sure! I wish your wife could talk with my better half for sure! My love of boots has always been a thorn in our relationship, and I understand, to a point. But, a little acceptance would go a long way for sure. We both know my love of boots is not going away. I work for the airlines and sometimes layover in downtown Chicago, or near ORD. Always looking for heel guys to hang out with. All the best. Don

The black outfit gets my vote for sure, the other outfit is great also, just fine in the office I'm sure... Let me know when you are headed out, would be so cool to have you on one of my flights!

"turned a few heads" is a good thing indeed!

OK, well first, let me congratulate you on a very quick evolution. One year since you ventured out in heels, and look at you now! Your efforts to tone your long lean physique have surely paid off, and you deserve to wear outfits like this with extreme pride and confidence. You really look great, don't mind admitting I'm very envious. Great taste in boots as well. As for your final question, I tried to respond in one of your other posts....

Oh boy, this seems like a tough question to answer. First, let me say that those tan boots are beautiful, and you look great. But, it sounds like you have a bit of a tough relationship with that boss/manager, so I don't want to advise anything that will strain that relationship any more than it is. I think you look amazing with the levis over the boots, but am guessing wearing the jeans to work might be pushing it. Next on my list, would be the tighter pair of black pants over the boots. Tell us more about what you have worn to work in terms of heels in the past... Would this be your first time wearing heels/boots to work? If you have worn heels/boots to work in the past, was there any negative pushback from management? If not, how about coworkers, although it is hard to imagine anything else but endless compliments coming from coworkers. If you have worn heels to work in the past, and there were no issues, then I would definitely wear the outfit with the tighter black pants and boots. You could wear the tan boots as well. Sorry that I probably haven't helped much, I just don't want to recommend anything that will cause issues at the work place.

I'm sure people have noticed and appreciate your style. Most people want to be polite, and won't stare or say anything. Many men notice also, and appreciate your style, they are just too nervous to say anything.

We do appreciate all your photos and efforts, but also understand if you are somewhat "burned out".

Glad you are better and back in heels for sure!

Hoping you will wear your boots later during the tour to "show her" that men can wear great boots and enjoy the benefits as well

great point indeed

I would agree, many men have a secret fascination, desire to wear heels, but very few actually act on those desires for the reasons you mentioned. It will many take "style pioneers" like yourself to help normalize this traditionally feminine fashion for men. The crazy heels/outfits seen on fashion runways are not all that helpful, most of these styles are way "over the top", nothing most guys would want to wear anyway. I would also agree that the thrill of wearing heels has subsided a bit for me as well. But, that can be a good thing, only because I am not shy or uneasy about wearing most of my boots publicly. I do the same thing, park my car as far out in the lot as possible, so I can enjoy a longer walk in my boots. And yeah, I don't mention my tall Hunter rain boots here much, because they have no heels. Love wearing them nonetheless, the glossy black finish coupled with the tall shafts that fit my "chicken legs" nicely feels and look great. D

Well said

Boy o boy, those boots would surely be hard to resist.

I would say that my "fascination" with boots and heels began when I was just a little kid. I have often wondered if this "fascination" is something I learned, or was I hardwired this way. Unfortunately, I waited until my late 40s-50s to actually allow myself to admit that I wanted to wear high heel boots and get some.... It has taken me many years since then to develop the courage and confidence to wear them in most any setting these days without the usual self imposed negative feelings. Thanks to all my friends here for your help. Don

You are sooo right. I am so happy to be over all that "fearfulness", can wear most of my boots just about anywhere without worry, which is the best feeling ever. I recently bought a pair of those Hunter gloss black tall "refined" rubber rain boots, love those as well. I just wish I could help some guy get over all the ridiculous fears I suffered with early on, without wasting valuable time and enjoyment. "Bootbuds", whether they be guys or gals, are a great way to ease your fears when out in public. "Confidence in numbers" seems to work.

I'm with you buddy. I think I look great in my boots, and no longer care what other's think. I suspect many guys notice my boots, and are secretly envious....

Great outfits indeed, those boots look great. Amazingly powerful and alluring when paired with the sports gear for sure...

For sure! Hoping I can join you sometime with my tall cowgirl boots and gloss black Hunter rain boots!