Will the third time be the charm? Another possible first outing

[heelguypa]

Ok, here it goes again, after years and years of failed attempts and different partners. Lol.

My current wife would not be very happy with me wearing high heels so it has been on the back burner. The last attempt when I got a new job it was snowing almost daily.
So new job and new attempt. I should be traveling to Montreal in the following weeks for a couple of weeks for training. So my mind immediately started wandering towards shoeeeees, lol. And planning on trying personally before purchasing. I found Aldo and Steve Madden, and I will also try other stores and malls. First check them them out and go with my gut feeling to try and buy. I am scouting ahead on Google maps possible stores to check out and maybe try on.

My must have parameters would be:
1. Must be an stilleto heel, the thinner the better
2. 3.5" to 4" heel
3. Closed shoe (one step at a time sandals not brave enough yet)

Then colorwise most likely black, patent or leather, but open to other low key not flashy colors, although I loooove pinks, florals, pastels, the "girlier" colors if you will, but once again not brave enough yet, probably later on.

Shoe style I am thinking a classic pointy toe pump, could be d'orsay style or with an ankle strap or slings, whichever looks and most importantly feels best when trying on.

It seems snow is on the forecast then maybe some ankle booties, and I know stilletos would be ill advised but that is fave, there are very few block and wedge styles I like, but we will see once I get there, and hopefully finally I can fulfill this fantasy.

Just as a comment I am so loving the new Larina ballerina pumps from Steve Madden  , https://www.stevemadden.com/products/larina-black-satin I can just picture these in black with a dark suit, would look amazing.

As usual any comments, tips words of encouragement are highly appreciated. 

[mlroseplant]

Good luck to you, I have many pairs of Steve Madden, from traditional looking pumps to platform sandals. I have found them to be pretty good for what they are. Like every other affordable shoe manufacturer, they've gotten away from using leather like they used to. At least their synthetic pumps, of which I have quite a few, are actually decent.

[heelguypa]

Yes I like their pumps a lot and they are a block away from Aldo. I mentioned Steve Madden mostly because of the shoes on the link, they are my current obsession, lol. So darn pretty and sexy 

[Gige]

Hi Heelguypa!

I think any of the "regular" members can appreciate your feelings. First, those Larina heels are wickedly gorgeous! If did not have seemingly 300 pairs of shoes and boots, you better believe that I would pick-up a pair!

When it comes to wearing heels out in public, there is "a lot" of advice on this forum about how to approach doing so - all of it good. Any man/male who has ever worn a pair of heels out in public knows exactly how you feel, and any one of them will tell you that the first time doing so is always the hardest. Trust me when I say that it gets easier the more you do it. I recommend that you read through those posts on the "for the guys" part of it as there are many great stories and encouragement about doing so. If it was not for this forum and the stories of others I read some time ago, I probably would have never summoned the courage to take that first step - literally. Now, rarely can I head out in a pair of heels without receiving a compliment.  I have said this in many previous posts but it is always worth repeating - "Those that mind don't matter and those that matter don't mind."

The photo included is the outfit I wore to work to day. So yes - it can be done and doing so is one step at a time. 

The outfit: Boots/Jessica Simpson Tulip; Boot chains from Shoebidoo (out of Utrecht).

 

 

 

Edited November 22, 2025 by Gige

[pebblesf]

Those JS boots are amazing, I had a similar pair.  Love the chains, great accessory

[heelguypa]

Hey guys, I will post an update this weekend, it was not at all what was planned but not a total loss and still amazing. 

[heelguypa]

OK guys for a overdue update.

When I arrived there, the day before it snowed and as I was told by the locals it was an unusually heavy snow for December and a lot colder, and then the second day an even more unusual snow storm was predicted for Wednesday. So any heeling was off the books, I barely saw any heels on the street if any and all were blocks and fairly low which makes sense.

However it was not a total loss, I was close to 2 malls downtown and I walked there and started stalking the stores waiting until there were no people or few people inside, went straight for the high heels that I liked and started browsing, not the usual go to the men's side and side eye the beautiful shoes while holding the ugly, heavy, uninspired bricks we are supposed to wear as shoes , lol. After a few asks if they could help I gathered my courage and asked for one in my size. I was at a store for a brand I did not know before I was in Canada, l'Intervalle. I was holding the most gorgeous, sexy and amazing pumps, specially the stilleto heel was shaped so beautifully and sexy, and was the thinnest stilleto I had ever seen which I adore. I am not exaggerating when I say they were about 2.5X2.5 mm (in between 1/16" and 1/8") at the heel tip, so freaking cool and amazing. I fell in love instantly. So I saw a a beautiful pair in 9 camel patent and asked for back patent, they checked and had none, let me clarify they had none on clearance but hey had it regular price I was not going to spend 90$ for a pair of pumps just to wear at the hotel, but hoped maybe a pair on clearance +40% off was ok. So asked for the other shoe for the camel patent in a 9 and they did not fit, these run very small, I am usually 8.5 and sometimes 9 but these were tiny. There as just a guy and a girl tending to the store, tried to get the girl to help me but she was on other things (I know I know, but I felt safer asking to try to a girl not a guy bit the bullet and asked anyway), I asked to try and he did not flinch just brought them and tried a 9 and they did not fit, then asked for a 10 to try on the size and he brought normal black leather and I tried them on in the store in public. I put them on, the girl was looking casually at me and it seemed to me she was surprised I was able to put them on sitting down easily then getting up and walking around. They were a tiny bit higher than expected but I still managed to walk gracefully, check myself in the mirror. The guy was completely unfazed. I said hold in one sec and removed my heavy coat, my sweater so I was dressed business casual straight from the office dark pant suit formal striped light blue and white shirt and black heels, looked amazing (I was so in the moment that I did not think about taking pictures). I removed the shoes and asked what else they had on sale and my size on that model (Teeva for those curious), he told me none on that store and they we closing soon, but I could go to another store site 5 minutes away or if I came back tomorrow they could have them sent to try and see them. I thanked him and told him I might or try to go to the other store. They girl went a little out of her way to help me out s and say good bye since they closed the gate, I had not noticed. 

So the next day I went to the next mall, there were more stores, Aldo, Steve Madden, call it spring and the other l'Intervalle. These stores closed much later than the other so they were busier at that time, and once again I stalked the stores. I walked in to Steve madden, started browsing the high heel pumps, holding them looking at them, and a sales girl approached, looked at me my feet and asked if I were a 9, she knew, caught off guard just said yes, she then said that they had very few I that size on the models I was looking at, she showed me others with a lower heel and she noticed it was not what I was looking for, she the said let me check what we have on your size, she came back and told me they had 8.5 and 10 and if I wanted to try, I agreed she brought patent black pumps hey we're too small and too big, while I was trying them on she brought lower heeled patent black pumps in 9to try and they fit like a glove amazingly comfortable but lowish for what I like I guess around 3" and also too expensive for this trip if I was not able to wear them. I did walk around with them a little after removing all the warm clothes I was dressed similarly to the day before, she complimented me on my look and walking skills, but also admited that higher heels would look much much better and if I wanted she could call me when they had more stock in a week or 2, black Friday had emptied their stock. I declined since I was leaving in a few days and thanked her a lot. In the store a woman trying on kitten heel boots just smiled and nodded I did not notice anyone else noticing me, maybe they did but I was on cloud nine on an amazing high. 

I then went to Aldo, same story walked straight into the high heel pumps, asked what was on sale and nothing I liked then walked out, 2 pumps were beautiful but not on sale and the store was busy so clerks were all around the place and did not want bother if I was not purchasing anything. 

Next stop was call it spring they had a beautiful pair of d'Orsay pumps, asked for black patent in size 9 the girl checked and told me they only had a dark brown which I did not like at all although they were cheap and would have bought them for the hotel, too bad, she tried selling them to me that the color was beautiful. I argued the shoe was beautiful but did not like the color. Tried looking at other styles and nothing caught my attention. Maybe a pair stiletto booties until I looked at them closer and I saw the had the stitches all trough the point and middle of the show which I hate but common on boots but that is a rant for another time. 

Finally the last store again L'intervalle but a different store from the previous day. I saw this one had 40% off for the whole store, and I darted straight to the heels I loved, they were right next to the cashier, a young girl, I stated asking if they the 40% also applied to on sale items, she said yes and asked what they on sale on that model size 10, she looked on the computer and said only off white patent and then showed me other choices with lower heels and told me that women often found these more comfortable I just agreed but said I wanted the other one because they were prettier, and asked to try them, she looked puzzled at first and told her they were for me, and proceeded to look for them came back and told me they were at the other store, and she could run to get them. I said maybe to try any other color first to make sure they fit so as to not make her run for them. For patent usually is a lot stiffer than regular leather so I wanted to try them as well like I dkde yesterday, she looked and said she had none on that size, I asked what else was on that size on the other store and if the discount also applied, she said yes, checked and called, however they were starting to close I did not notice the time. I just said I might come back tomorrow. She let me check everything we have on your size so if you come back tomorrow you have a better idea, just being a good sales person. Not much just 2 more choices. I thanked her and she kinda eagerly said she said her shift starts at 4pm and she would gladly run to the other store to get me those. I smiled back and left.

The next two days were a lot colder and did not want to leave the hotel room after work so there ends my adventure, not what I hoped for but still great.

I have to admit that I used all of my almost non existent literary talents to recount as accurately as possible while making it fun.

Now to be wait for my next trip in a few months to try again.

 

Thanks for listening to my ramblings. 

[Shyheels]

Sounds like you had quite a time shopping. The staff at these places sound helpful and non-judgemental. which is nice. You're fortunate that you can go shopping. My feet are much too large for that. I can buy nice heels - very nice ones in fact - but ether custom or special order.  

[Cali]

Your getting bolder in your shopping. Next time go straight in look and ask. Don't wait until there are less customers.

I wear heels all the time so when I go into a shop they know I'm looking for myself. Many times I get better service because they view me as a higher chance of a 'sale' than women just looking.

[pebblesf]

17 hours ago, heelguypa said:

OK guys for a overdue update.

When I arrived there, the day before it snowed and as I was told by the locals it was an unusually heavy snow for December and a lot colder, and then the second day an even more unusual snow storm was predicted for Wednesday. So any heeling was off the books, I barely saw any heels on the street if any and all were blocks and fairly low which makes sense.

However it was not a total loss, I was close to 2 malls downtown and I walked there and started stalking the stores waiting until there were no people or few people inside, went straight for the high heels that I liked and started browsing, not the usual go to the men's side and side eye the beautiful shoes while holding the ugly, heavy, uninspired bricks we are supposed to wear as shoes , lol. After a few asks if they could help I gathered my courage and asked for one in my size. I was at a store for a brand I did not know before I was in Canada, l'Intervalle. I was holding the most gorgeous, sexy and amazing pumps, specially the stilleto heel was shaped so beautifully and sexy, and was the thinnest stilleto I had ever seen which I adore. I am not exaggerating when I say they were about 2.5X2.5 mm (in between 1/16" and 1/8") at the heel tip, so freaking cool and amazing. I fell in love instantly. So I saw a a beautiful pair in 9 camel patent and asked for back patent, they checked and had none, let me clarify they had none on clearance but hey had it regular price I was not going to spend 90$ for a pair of pumps just to wear at the hotel, but hoped maybe a pair on clearance +40% off was ok. So asked for the other shoe for the camel patent in a 9 and they did not fit, these run very small, I am usually 8.5 and sometimes 9 but these were tiny. There as just a guy and a girl tending to the store, tried to get the girl to help me but she was on other things (I know I know, but I felt safer asking to try to a girl not a guy bit the bullet and asked anyway), I asked to try and he did not flinch just brought them and tried a 9 and they did not fit, then asked for a 10 to try on the size and he brought normal black leather and I tried them on in the store in public. I put them on, the girl was looking casually at me and it seemed to me she was surprised I was able to put them on sitting down easily then getting up and walking around. They were a tiny bit higher than expected but I still managed to walk gracefully, check myself in the mirror. The guy was completely unfazed. I said hold in one sec and removed my heavy coat, my sweater so I was dressed business casual straight from the office dark pant suit formal striped light blue and white shirt and black heels, looked amazing (I was so in the moment that I did not think about taking pictures). I removed the shoes and asked what else they had on sale and my size on that model (Teeva for those curious), he told me none on that store and they we closing soon, but I could go to another store site 5 minutes away or if I came back tomorrow they could have them sent to try and see them. I thanked him and told him I might or try to go to the other store. They girl went a little out of her way to help me out s and say good bye since they closed the gate, I had not noticed. 

So the next day I went to the next mall, there were more stores, Aldo, Steve Madden, call it spring and the other l'Intervalle. These stores closed much later than the other so they were busier at that time, and once again I stalked the stores. I walked in to Steve madden, started browsing the high heel pumps, holding them looking at them, and a sales girl approached, looked at me my feet and asked if I were a 9, she knew, caught off guard just said yes, she then said that they had very few I that size on the models I was looking at, she showed me others with a lower heel and she noticed it was not what I was looking for, she the said let me check what we have on your size, she came back and told me they had 8.5 and 10 and if I wanted to try, I agreed she brought patent black pumps hey we're too small and too big, while I was trying them on she brought lower heeled patent black pumps in 9to try and they fit like a glove amazingly comfortable but lowish for what I like I guess around 3" and also too expensive for this trip if I was not able to wear them. I did walk around with them a little after removing all the warm clothes I was dressed similarly to the day before, she complimented me on my look and walking skills, but also admited that higher heels would look much much better and if I wanted she could call me when they had more stock in a week or 2, black Friday had emptied their stock. I declined since I was leaving in a few days and thanked her a lot. In the store a woman trying on kitten heel boots just smiled and nodded I did not notice anyone else noticing me, maybe they did but I was on cloud nine on an amazing high. 

I then went to Aldo, same story walked straight into the high heel pumps, asked what was on sale and nothing I liked then walked out, 2 pumps were beautiful but not on sale and the store was busy so clerks were all around the place and did not want bother if I was not purchasing anything. 

Next stop was call it spring they had a beautiful pair of d'Orsay pumps, asked for black patent in size 9 the girl checked and told me they only had a dark brown which I did not like at all although they were cheap and would have bought them for the hotel, too bad, she tried selling them to me that the color was beautiful. I argued the shoe was beautiful but did not like the color. Tried looking at other styles and nothing caught my attention. Maybe a pair stiletto booties until I looked at them closer and I saw the had the stitches all trough the point and middle of the show which I hate but common on boots but that is a rant for another time. 

Finally the last store again L'intervalle but a different store from the previous day. I saw this one had 40% off for the whole store, and I darted straight to the heels I loved, they were right next to the cashier, a young girl, I stated asking if they the 40% also applied to on sale items, she said yes and asked what they on sale on that model size 10, she looked on the computer and said only off white patent and then showed me other choices with lower heels and told me that women often found these more comfortable I just agreed but said I wanted the other one because they were prettier, and asked to try them, she looked puzzled at first and told her they were for me, and proceeded to look for them came back and told me they were at the other store, and she could run to get them. I said maybe to try any other color first to make sure they fit so as to not make her run for them. For patent usually is a lot stiffer than regular leather so I wanted to try them as well like I dkde yesterday, she looked and said she had none on that size, I asked what else was on that size on the other store and if the discount also applied, she said yes, checked and called, however they were starting to close I did not notice the time. I just said I might come back tomorrow. She let me check everything we have on your size so if you come back tomorrow you have a better idea, just being a good sales person. Not much just 2 more choices. I thanked her and she kinda eagerly said she said her shift starts at 4pm and she would gladly run to the other store to get me those. I smiled back and left.

The next two days were a lot colder and did not want to leave the hotel room after work so there ends my adventure, not what I hoped for but still great.

I have to admit that I used all of my almost non existent literary talents to recount as accurately as possible while making it fun.

Now to be wait for my next trip in a few months to try again.

 

Thanks for listening to my ramblings. 

Sounds like quite the shopping experiences, so sorry they didn't have your sizes in the styles you wanted, so frustrating indeed...