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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.

I love sweater dresses as a whole. My favorite dress of my wife's is one. You would have to know us, but we banter back and forth a lot and often make these silly bets. Well, we were at the local mall and eating at the food court and beside us was a small woman's boutique. Way up high they had this sweater and so it began. I said it was a sweaterdress, and the wife said it was way too short to be a dress and was just a long sweater. So after eating we asked the clerk and sure enough I was right, it was a sweaterdress. A good clerk, her next words were, "would you like to buy it?" Sure enough, one in her size went home with us. I actually see it in several pictures now. We buy and sell a lot of property and on one such purchase, we are pictured with her wearing it. She likes it because she can tame its truncated hemline with leggings for a demure look, or go sassy and leave it short pairing it with pantyhose/tights.

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.

I think you might be right. I shall work on that. I really, really want to master these!

@Shyheels Which issues do you have with walking heel to toe? My new boots arrived yesterday! Already wore them a bit, so far I can say they fit perfect and look great. Walking was difficult on the first try, I could feel the extra height to the Hot Chicks. I'll definitely keep them, but it will probably take a while until I can actually wear them out. First have to wear them at home a lot to break them in and also get used to the height. My goal is still to use them as a Hot Chick replacement for winter, so I have to hurry up to be ready soon for wearing them out 🙂

I just feel really awkward in them, clomping around. Some of it is the subtle sideways tilt in the floor but a lot of it feels like simple unfamiliarity - as though I’ve never work heels.i know I’m not walking heel to toe and that’s bound to be a major impact. i will try again tomorrow and see if i can analyse my technique snd what exactly I am doing wrong, and why the hesitancy.

I would really love to be able to walk effortlessly in these. I just have to find the space and time to practice