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What's Your Next Challenge Wearing Heels?

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Great milestone! Thanks for sharing. Good luck on getting more fashionable outfits. Steve

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Going into a store or a mall. I would really rather do it out of town so I'll probably wait until the next time I travel.

Going into store - check.

I had to run some errands for work today. This morning I got coffee in my 5-inch black patent platform pumps from Torrid so they were in my car. One of my stops was Walgreens for some Polysporin and band aids. On went my pumps and I did it. Extra cool was the fact that the first aid items were in the opposite corner from the entrance.

It was really fun.

Best,

AZShoeNut

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I would love to do the skinny jeans and knee high boots look, however, until I drop a bit of weight, I would look too top heavy. I have a really slender body from the belt down, but I have just too much going on in the waist area right now, unfortunately. I am sure I would not get too many negative comments, but I would just feel too self concious to be comfortable in that look.

Same here. Thinking twice, I wonder how women deal with slight weight increases : back to clothes without any shape or assume ?

I have watched a TV program on relooking women that were not assuming their feminity or extra weight or both. The results were unbelievable. A great confidence booster.

Only problem : need a second skinny jeans for high weight times, which has been to be bought at the right time of year... Hard to explain this expense to the wife...

Longline waterfall cardigans are great if you feel self-conscious about wearing skinny jeans (assuming you can squeeze into them of course). A darker coloured cardigan with lighter coloured jeans/leggings can help to rebalance the usual male broad shoulders and narrow hips.

Nice train journey Gudulitooo, the walk along the train platform must have been a fantastic feeling!

AZShoeNut, I agree it was quite a challenge for me to wear flats the first time. I was curious to see if they would be noticed and get reactions the same way as heels, and I also felt that some of the confidence from the extra height of the heels was missing.

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Thanks sleekheels and also for the tip. I had never thought about longline waterfall cardigans, my wife hasn't any. Is this only a clothe for style, or does it have any warming capablities ? As for the train platform walk, I discovered the shoes ran a bit small during the platform exchange and got a nice blister.

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I think for next summer I would like to wear Capri pants with a pair of 8" heels. Thighbootguy, I think I will try the thigh boots this winter to sounds fun

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Just thought of a challenge of my own: A long sweater with leggings and knee boots. I've seen women sport that ensemble and thinks it looks cool! I'd certainly like to give that a try.

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Oooh, Jeff, that is a good idea. I love the style on women. It just looks so comfy. Enjoy!

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Oooh, Jeff, that is a good idea. I love the style on women. It just looks so comfy. Enjoy!

It is comfy! I sport a similar look frequently with skinny jeans,

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I have two challenges that you guys should try! I've already done it, so its not a challenge anymore. 1. Wear shorter pants that expose more heel. 2. Change your rubber heel tips to plastic or steel. You can worry if people can accept you in heels. Just as long as you accept yourself! If you like to dress a certain way inside your house, then there is no reason you can't do it outside. Then again, its easier you me because I live in a cosmopolitan city. Toronto. My friends are jealous because I can fit into sexy clothes and slutty shoes.

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My next challenge is going to be strappy heels or something in a color other than black. Maybe both. Nikki

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I am already doing jeans tucked into my boots, which is my only way of going out heeling. Most crowded place so far has been going to a movie theater during daytime hours. My next challenge is to go into a large crowded mall on a Saturday afternoon, assuming that there will be giggly teenagers ready to capture what they saw on their iPhones.

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Good luck with the mall visit. I doubt anyone else would care other than the teenagers. :)

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I want to wear boots with my pants tucked it. I've seen a lot of guys in the subway do it. What I don't get are the new fashionable rain boots. Butt ugly!

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Saw an interesting and dynamic look downtown late this morning, sadly, it's a look we as men are incapable of emulating. The look in question was a young woman in her mid to late 20's, wearing a blazer over a mock turtleneck, a wide faux croc belt, leggings and riding boots, all in black. Needless to say, I found that to have been quite a head turner, mainly because of the top and leggings and nothing else which emphasized her figure, and that's something men can't copy, especially in public, not even me, but still, I might be just crazy enough to give that a try with a pair of high heeled boots, just to see what that would look like.

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leggings and riding boots, all in black.

One of my co-workers often wears black leggings and strappy stiletto heels or pumps. My heart starts racing every time I see her.

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Just thought of a challenge of my own: A long sweater with leggings and knee boots. I've seen women sport that ensemble and thinks it looks cool! I'd certainly like to give that a try.

Funnily enough, that exactly describes my outfit today!

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Just thought of a challenge of my own: A long sweater with leggings and knee boots. I've seen women sport that ensemble and thinks it looks cool! I'd certainly like to give that a try.

I've tried that once (capuccino coloured knit dress with black leggings, brown 3½" knee boots, wide brown belt and a denim jacket). It's one of my favourite outfits but that knit dress is warm and I've been waiting for winter to wear it again. I totally agree it's a really cool look and very comfortable.

Saw an interesting and dynamic look downtown late this morning, sadly, it's a look we as men are incapable of emulating. The look in question was a young woman in her mid to late 20's, wearing a blazer over a mock turtleneck, a wide faux croc belt, leggings and riding boots, all in black. Needless to say, I found that to have been quite a head turner, mainly because of the top and leggings and nothing else which emphasized her figure, and that's something men can't copy, especially in public, not even me, but still, I might be just crazy enough to give that a try with a pair of high heeled boots, just to see what that would look like.

I've tried a similar look a few times: blazer over a turtleneck with either leggings or skinny jeans and knee boots (once with flat heels, a couple of times with heels). For sure I don't think for a moment that I look half as good as some women do, but I felt totally comfortable with how the look was working for me. Maybe the "all in black" was also part of what emphasized her figure so effectively? I mixed up the colours a bit (e.g. cream turtleneck under a tweed blazer with blue denim jeans and brown boots) which maybe distracts from my figure.

Thanks sleekheels and also for the tip. I had never thought about longline waterfall cardigans, my wife hasn't any. Is this only a clothe for style, or does it have any warming capablities ?

I'm no fashion guru, but my personal experience is that the thinner style open-front ribbed cardigans are the nicest look, and a thin long-sleeve top can be worn underneath (plus a teeshirt under that) for warmth without bulking up the shoulders too much. Something like the photo (that's not me of course!) would work with a turtleneck and heels (court shoes or ankle/knee boots). I have a chunkier longline cardigan and I think that works better with bootcut jeans and heels to avoid looking too top-heavy. That's just what works for me but I hope it gives you some ideas to experiment with.

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I've tried that once (capuccino coloured knit dress with black leggings, brown 3½" knee boots, wide brown belt and a denim jacket). It's one of my favourite outfits but that knit dress is warm and I've been waiting for winter to wear it again. I totally agree it's a really cool look and very comfortable.

Well, then! I'm gonna have to search for a long sweater (or a knit dress) and leggings and give that outfit a try as it certainly sounds intriguing.

I've tried a similar look a few times: blazer over a turtleneck with either leggings or skinny jeans and knee boots (once with flat heels, a couple of times with heels). For sure I don't think for a moment that I look half as good as some women do, but I felt totally comfortable with how the look was working for me. Maybe the "all in black" was also part of what emphasized her figure so effectively? I mixed up the colours a bit (e.g. cream turtleneck under a tweed blazer with blue denim jeans and brown boots) which maybe distracts from my figure.

I would agree that the all black part of that equation was what drew my eyes to her figure. Speaking of which, yeah, it would certainly help to have something in the way of a figure to wear a turtleneck and leggings and nothing else, but I'd certainly like to try that with skinny jeans which I do have.

I'm no fashion guru, but my personal experience is that the thinner style open-front ribbed cardigans are the nicest look, and a thin long-sleeve top can be worn underneath (plus a teeshirt under that) for warmth without bulking up the shoulders too much. Something like the photo (that's not me of course!) would work with a turtleneck and heels (court shoes or ankle/knee boots). I have a chunkier longline cardigan and I think that works better with bootcut jeans and heels to avoid looking too top-heavy. That's just what works for me but I hope it gives you some ideas to experiment with.

Hmm! Now that's a nice, casual look! Color me intrigued!

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I tried the pants tucked into the boots look a few times, but somehow it doesn't look right. In too skinny for that look I think? But, flare jeans the are reallt tight in the thighs with pumps on, with exposing a little heel looks killer on me. I saw a woman In walmart with long tight bootcut pants scratching the floor with pointy stilleto pumps on. I wonder how high the heels were. But that's the style I like. So, my next challenge is to wear pointy stilletos with loud f___in' heel tips. I could do that very easily!

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Go for it, Pumpcat. Just go do it and report back. That's your homework assignment for this week! LOL Steve

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I can't wait to get home to do my homework. Got to make the honour roll! Ill let you guys know when I do it. My latest look was pumps with a narrow square toe box, with long, tight pants. Btw, my heels were 4.5". Love the shoes so much!

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I am already doing jeans tucked into my boots, which is my only way of going out heeling. Most crowded place so far has been going to a movie theater during daytime hours. My next challenge is to go into a large crowded mall on a Saturday afternoon, assuming that there will be giggly teenagers ready to capture what they saw on their iPhones.

I already wear skinny jeans tucked inside my heeled knee boots with a 3" stacked heel. I also have men's Frye boots with 2 1/2" block heels that I wear with jeans tucked inside. I have had compliments from both men and women with the tucked in look. That look is not only for women, but men can wear that look too even if they don't wear heeled boots and wear men;'s riding boots.

My next challenge will be to wear leggings with knee boots. I bought a long length sweater from the tall men's shop that goes to about 3" above my knee which will work fine to wear with leggings so that nothing is revealed!

Happy Heeling,

bluejay

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Okay, here is the real challenge: I want to be at ease, relaxing without my guard up in my heels. My first next challenge was to wear heels into a store – check. My next challenge was to wear my loud flat wedges out. That would have been a check this morning but my schedule shrunk when the baby’s diaper leaked and we had a bath and a load of laundry added to the morning. I first started flirting with the idea of wearing heels out and about when I would start my morning with coffee at Starbucks in downtown Tempe, AZ. I would watch these gals wearing great shoes coming and going and really wanted to do it too. Recently I asked myself if I am actually achieving my original goal for wearing heels out and about. Contemplating that thought I realized that a big part of what I appreciated about the women wearing their heels around the downtown area was the fact that they were so at ease. So, my challenge is to wear my heels and be relaxed and at ease about it. I want to enjoy my time standing in line and not wondering about whom each person is that walks into the coffee house behind me and to take my strides in peace and joy. So, my challenge is not a “feel the fear and do it anyway” kind of challenge. This is a challenge of getting my mind to relax and remember why it is that I wanted to wear heels in the first place. Best, AZShoeNut

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AZShoeNut, I am with you on this challenge!! Heading off to the post office with the boots in my avatar. Jim

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Larry and Jim, I think the relaxed attitude comes with time, patience, and doing it so often that you forget you're wearing heels. Every time you go out in heels you build up confidence a little, and eventually you'll wonder what all the fuss was about. So just continue what you're doing. You're on the right track. Just don't expect it to happen overnight. It will take a lot longer, but you'll get there, and it's worth going after. Steve

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AZShoeNut,

I am with you on this challenge!! Heading off to the post office with the boots in my avatar.

Jim

Hey Jim, Have fun in your boots!

Larry and Jim,

I think the relaxed attitude comes with time, patience, and doing it so often that you forget you're wearing heels. Every time you go out in heels you build up confidence a little, and eventually you'll wonder what all the fuss was about. So just continue what you're doing. You're on the right track. Just don't expect it to happen overnight. It will take a lot longer, but you'll get there, and it's worth going after.

Steve

Thanks for the perspective, Steve. I think you hit the nail on the head. I think that I will just try to be mindful when I am out heeling to relax a bit and enjoy.

Best,

AZShoeNut

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My next challenge will be to wear leggings with knee boots. I bought a long length sweater from the tall men's shop that goes to about 3" above my knee which will work fine to wear with leggings so that nothing is revealed!

Happy Heeling,

bluejay

Sounds cool! By all means, let us know how that turns out as that's a look I'm eager to try myself!

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Wear my cute (but loud) wedge flats out - check.

I had a very nice coffee this morning. I relaxed a good deal more than I usually do too! I even read an article in a magizene.

Best,

Larry

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I belong to a campground in northern Michigan, we go there most weekends in the summer. I haven't heeled there yet, but am going to put it on my bucket list for this summer.

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