Another "first" moment

[Gige]

As we all know, there is a “first time” for all events in life that are certainly worth remembering for one reason or another. Over this past Halloween, I had one such event that covered two firsts for me – traveling in heels and being “out and about” in heels with my wife, both of which were delightful. This is just a short recap of both as I believe that they are worth celebrating and/or remembering.

On the day before Halloween, I was to meet my wife in Boston for a long weekend to celebrate our wedding anniversary and tour a city that, despite our worldly travels over the years, we had not yet visited. I was to depart from St. Louis while she was to depart from Amsterdam and we would meet each other at Logan Airport in Boston. For this leg of the journey, I sported a simple Anne Klein - 3” heel, black ankle boot. Admittedly, I was feeling a few nerves as I entered the terminal as I reasoned that this was the most crowded place to date in which I wore heels. Regardless, all went smoothly from entry to departure.

As the flight neared Boston, I noticed that I was starting to become a bit anxious because of the fact that when my wife would actually see me, it would be the first time she would do so in “real-life,” not just from a picture. Thus, I was unsure if her reaction would be different or not. Nonetheless, we were happy to be reunited and headed to our hotel. There, I eventually changed into jeans and my trainers as we headed out to dinner.  

The next day (Halloween) we spent walking parts of Boston’s 2.5 mile long Freedom Trail and I am glad I did so in my trainers! For the evening, we headed to Salem, Massachusetts (site of the infamous witch trials in the late 17th century) but as we were heading there via public transportation, we both decided to start the trek in our trainers and change footwear while en route. I had selected my 4” Giaro, pointed-toe, black wedge boots as the choice for the event. Just before arrival at the town's train station, I switched footwear and then we headed out to join the festive environment that it was (think Mardi Gras). After our celebratory dinner, we strolled the town’s streets and as we stopped to speak with a local craft vender, a young Asian woman noticed me. Although I do not remember her specific words, they were along the lines of “You’re a fashion icon” and insisted that I pose for a picture with her. Not a problem as I am always happy to do so. About an hour later, however, the boots had to come off not because of my feet hurting but due to the fact that my thighs and calves were aching from the afternoon walk around Boston and walking in heels was not doing them any favors. 

Friday did not see me in boots/heels at all and Saturday, I was wearing flat heeled, black microfiber just over-the-knee boots as we visited a friend for dinner outside of Boston. As Saturday’s boots were flat, I will not go into details of those, although the outfit was rather attractive!

Sunday morning saw us visiting one last historical sight and a final shopping excursion before heading to the airport for our flight to St. Louis. The plan was to spend the morning activities in my trainers and then switch into a pair of Naturalizer, black leather, 2.5” knee high boots for the trip back to my part of the world. Unfortunately, we arrived back at our hotel later that expected and due to some “issues” of another pushy tour group, departed for the airport a bit later than we hoped. So, once we arrived at Logan Airport, I quickly changed into my boots and made our way to the gate. The “problem” with the boots I was wearing was that this was their initial outing and they were rather tight, especially the left foot. 

I have a great leather softening spray I use (purchased on Amazon) to help with the breaking in process but as I left this back at my place, I just had to deal with it. I decided to see if walking around the airport would help loosen them up a bit, so I took a stroll around to other gates and as I did so, a young woman with body piercing just about everywhere possible commented that my outfit was “sensational!” I profusely thanked her for comments and headed back towards my departure gate, taking the long way back so that I could “strut my stuff” and everyone in the terminal could see me – boy did that feel great!  

Overall, the new boots were not “too” bad but by the time I actually was enroute back to my place, the left boot had to come off as it was very much pushing against my swollen foot. As I write this, I have sprayed the boot with the leather softener and I am wearing it with multiple pairs of thick socks to help stretch it out a bit. 

At St. Louis - 

In Salem (MA - no "real" witches found!)

At Logan (Boston) Airport

Edited November 4 by Gige
Correct font issues

[Cali]

20 minutes ago, Gige said:

...two firsts for me – traveling in heels and being “out and about” in heels...

I have been flying domestically and internationally in heels for over a decade. The only extra issue is I need to take my heels off to go through the metal detector. The zipper sets off the machine every time. Knee high boots draw attention every time. But I have yet to travel in a skirt. Maybe one day (soon).

[Gige]

14 minutes ago, Cali said:

I have been flying domestically and internationally in heels for over a decade. The only extra issue is I need to take my heels off to go through the metal detector. The zipper sets off the machine every time. Knee high boots draw attention every time. But I have yet to travel in a skirt. Maybe one day (soon).

Surprisingly, no issues with zippers setting off metal detectors. 

[Shyheels]

Very nice boots. I’m always in boots - usually knee boots either low or medium heels (up to 3.5”)

sounds like you had a lovely weekend with your wife. I’ve not been to Boston in many years - about 30 I think - but I used to like the place way back when

[Gige]

1 hour ago, Shyheels said:

Very nice boots. I’m always in boots - usually knee boots either low or medium heels (up to 3.5”)

sounds like you had a lovely weekend with your wife. I’ve not been to Boston in many years - about 30 I think - but I used to like the place way back when

I was last in Boston 38 years ago, so to me, I cannot count those as 'having been there" by any stretch of the imagination. 

THanks for the compliments.

[mlroseplant]

I have never actually flown in heels before. Nowadays I have grown to dislike the whole experience, such that I'm not sure it would improve my attitude even with heels!

[Shyheels]

1 hour ago, mlroseplant said:

I have never actually flown in heels before. Nowadays I have grown to dislike the whole experience, such that I'm not sure it would improve my attitude even with heels!

I totally agree. I was a platinum frequent flyer for many years with the One World alliance but I now absolutely avoid flying - I loathe it.

[pebblesf]

21 hours ago, Gige said:

As we all know, there is a “first time” for all events in life that are certainly worth remembering for one reason or another. Over this past Halloween, I had one such event that covered two firsts for me – traveling in heels and being “out and about” in heels with my wife, both of which were delightful. This is just a short recap of both as I believe that they are worth celebrating and/or remembering.

On the day before Halloween, I was to meet my wife in Boston for a long weekend to celebrate our wedding anniversary and tour a city that, despite our worldly travels over the years, we had not yet visited. I was to depart from St. Louis while she was to depart from Amsterdam and we would meet each other at Logan Airport in Boston. For this leg of the journey, I sported a simple Anne Klein - 3” heel, black ankle boot. Admittedly, I was feeling a few nerves as I entered the terminal as I reasoned that this was the most crowded place to date in which I wore heels. Regardless, all went smoothly from entry to departure.

As the flight neared Boston, I noticed that I was starting to become a bit anxious because of the fact that when my wife would actually see me, it would be the first time she would do so in “real-life,” not just from a picture. Thus, I was unsure if her reaction would be different or not. Nonetheless, we were happy to be reunited and headed to our hotel. There, I eventually changed into jeans and my trainers as we headed out to dinner.  

The next day (Halloween) we spent walking parts of Boston’s 2.5 mile long Freedom Trail and I am glad I did so in my trainers! For the evening, we headed to Salem, Massachusetts (site of the infamous witch trials in the late 17th century) but as we were heading there via public transportation, we both decided to start the trek in our trainers and change footwear while en route. I had selected my 4” Giaro, pointed-toe, black wedge boots as the choice for the event. Just before arrival at the town's train station, I switched footwear and then we headed out to join the festive environment that it was (think Mardi Gras). After our celebratory dinner, we strolled the town’s streets and as we stopped to speak with a local craft vender, a young Asian woman noticed me. Although I do not remember her specific words, they were along the lines of “You’re a fashion icon” and insisted that I pose for a picture with her. Not a problem as I am always happy to do so. About an hour later, however, the boots had to come off not because of my feet hurting but due to the fact that my thighs and calves were aching from the afternoon walk around Boston and walking in heels was not doing them any favors. 

Friday did not see me in boots/heels at all and Saturday, I was wearing flat heeled, black microfiber just over-the-knee boots as we visited a friend for dinner outside of Boston. As Saturday’s boots were flat, I will not go into details of those, although the outfit was rather attractive!

Sunday morning saw us visiting one last historical sight and a final shopping excursion before heading to the airport for our flight to St. Louis. The plan was to spend the morning activities in my trainers and then switch into a pair of Naturalizer, black leather, 2.5” knee high boots for the trip back to my part of the world. Unfortunately, we arrived back at our hotel later that expected and due to some “issues” of another pushy tour group, departed for the airport a bit later than we hoped. So, once we arrived at Logan Airport, I quickly changed into my boots and made our way to the gate. The “problem” with the boots I was wearing was that this was their initial outing and they were rather tight, especially the left foot. 

I have a great leather softening spray I use (purchased on Amazon) to help with the breaking in process but as I left this back at my place, I just had to deal with it. I decided to see if walking around the airport would help loosen them up a bit, so I took a stroll around to other gates and as I did so, a young woman with body piercing just about everywhere possible commented that my outfit was “sensational!” I profusely thanked her for comments and headed back towards my departure gate, taking the long way back so that I could “strut my stuff” and everyone in the terminal could see me – boy did that feel great!  

Overall, the new boots were not “too” bad but by the time I actually was enroute back to my place, the left boot had to come off as it was very much pushing against my swollen foot. As I write this, I have sprayed the boot with the leather softener and I am wearing it with multiple pairs of thick socks to help stretch it out a bit. 

At St. Louis - 

In Salem (MA - no "real" witches found!)

At Logan (Boston) Airport

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.  

1 hour ago, Shyheels said:

I totally agree. I was a platinum frequent flyer for many years with the One World alliance but I now absolutely avoid flying - I loathe it.

I hate it too!  Only a few more months before retiring from AA.  

[Jkrenzer]

8 hours ago, pebblesf said:

 

I have flown in heels many times in the past. I have stopped however if only for the fact that the altitude lower air pressure causes feet to swell some. I've flown 12 hrs from Brazil in heels, 5 inch loafers ( wish I still had these shoes) but in flight I had to remove them even though I untightened the laces. Not comfortable. My non heels were checked in so no changing.

[Cali]

I had a 40 hour nightmare of cancel flights, switching airports, delayed flights, and airport sleeping in my Sydney to LAX and then home in fall 2023. Wore my 4 inch booties for almost all of the time.

[Gige]

Not to get "too" far off topic... I also have come to loathe traveling. I usually enjoy the place to which I am traveling but getting here is often such a headache! I am sure we all have horrible stories of severally delayed/cancelled flights, lost luggage, lack of service, etc., and my list of that which bothers me about it is quite extensive. Not to disparage anyone who works for the travel industry in any capacity, but it seems that any way every last nickel can be squeezed out of the traveler is going to be done. This fee for that, that fee for this, a fee for charging a fee...

I did, however, enjoy traveling in heels and, in particular, strolling around the terminal in a skirt and boots for all to see. As much as I wither at the prospect of the next flight I have to catch, I can not wait to do it again!

On 11/5/2024 at 8:27 AM, pebblesf said:

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.  

Nope - AA from BOS -> STL.

[pebblesf]

8 hours ago, Gige said:

Not to get "too" far off topic... I also have come to loathe traveling. I usually enjoy the place to which I am traveling but getting here is often such a headache! I am sure we all have horrible stories of severally delayed/cancelled flights, lost luggage, lack of service, etc., and my list of that which bothers me about it is quite extensive. Not to disparage anyone who works for the travel industry in any capacity, but it seems that any way every last nickel can be squeezed out of the traveler is going to be done. This fee for that, that fee for this, a fee for charging a fee...

I did, however, enjoy traveling in heels and, in particular, strolling around the terminal in a skirt and boots for all to see. As much as I wither at the prospect of the next flight I have to catch, I can not wait to do it again!

Nope - AA from BOS -> STL.

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