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.