What's Your Next Challenge Wearing Heels?

[SleekHeels]

This year I wore my heels with leggings and skinny jeans (mostly tucked into knee boots) and that felt like a big step forwards from hiding heels under bootcut trousers. I want to wear my heels with my 3/4 length cropped trousers (I love that look especially with slingbacks/ankle-straps like the ones below) so that's my next challenge but it's winter now - it's too cold and I prefer that look with bare legs so I'll have to wait until next spring/summer. For now my next challenge will be the court heels with skinny jeans look, which will be a step forwards from just boots. Do you set yourself challenges to break new ground when you wear your heels? If so, what's your next challenge?

[Curt]

I don't set any challenges. I just dress the way I want. I would tuck the pants inside the boots, but my legs are so skinny, plus I don't have any skinny jeans. I would love to wear pumps with stockings and a skirt, but I don't look 100% like a girl so it won't work. I'm not into the crossdressing look. I just like to add heels to whatever I'm wearing. But, I find that heels look better with girls jeans, than with guys. Just my opinion.

[krazyhusband]

Before, I use to wear only mens bootcut jeans. Covers most of the heel(shoe). Now I have been wearing straight cut jeans. It shows more of the toe area and just a tiny bit of the heel. Depending on what heel I wear, its a little bit more obvious that I am wearing heels. Also I have not been replacing the heel tips with rubber, or cover the sole of the shoe with rubber. So it also sounds like more of a heel,which I like.

[Shafted]

I don't set any challenges. I just dress the way I want

The same here.

[Heelster]

skinny jeans and pumps

[AZShoeNut]

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.

[Heelster]

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.

That's what I do.

[hoverfly]

Pants tucked in knee high boots with a low heel.

[dbert]

I have only worn heels pretty consealed under long trousers before. I'd like to wear knee high boots with skinny jeans, something like the picture attached.

[FreshinHeels]

I have only worn heels pretty consealed under long trousers before. I'd like to wear knee high boots with skinny jeans, something like the picture attached.

Same here but haven't got the courage for that.

Either way I'm happy way things are going with heeling.

So I havent got real challenges but just want to continue on this road while I build up confidence.

Edited November 24, 2012 by FreshinHeels

[SF]

My only suggestion is get out there and "just do it." You may be scared, you will be nervous. Yes some folks will notice, and some won't. Some may make inappropriate comments and some may even compliment you. Most won't even notice or care. If asked, tell 'em the truth, whatever it may be. I usually tell folks that I like shoes, found these in my size and enjoy wearing them!! Set a goal no not, it's up to you. I enjoy wearing heels and chose not to confine my heeling to my home, so I ventured out. I wasn't easy, but I don't regret a minute of the experience. Just be happy with yourself. To quote a line from the movie Napoleon Dynamite, "Follow your dreams Pedro." Happy Thanksgiving and Merry Christmas to all.... sf

[Thighbootguy]

This year I wore my heels with leggings and skinny jeans (mostly tucked into knee boots) and that felt like a big step forwards from hiding heels under bootcut trousers. … For now my next challenge will be the court heels with skinny jeans look, which will be a step forwards from just boots.

First, there is no such thing as “just boots”.

If you’re comfortable with legging and skinny jeans tucked into knee boots and are looking for a bit more of a challenge, now that winter is here, I seriously suggest leather thigh boots. The look is absolutely smashing and on a practical side, they are warm.

[JeffB]

First, there is no such thing as “just boots”.

If you’re comfortable with legging and skinny jeans tucked into knee boots and are looking for a bit more of a challenge, now that winter is here, I seriously suggest leather thigh boots. The look is absolutely smashing and on a practical side, they are warm.

I couldn't agree more! TBG turned me onto thigh high boots a few years ago and I haven't looked back as they're absolutely awesome to wear, and yeah, in this chilly weather, they ARE warm on even the coldest day! If you want a challenge, thigh boots would certainly qualify!

[wood&metal]

skinny jeans and pumps

I like the look, and I'd like to try it.. I think first though, I'd like to try skinny jeans with a pair of ankle boots because I'm not to certain about myself in pumps..

A little off topic, but I'd like to try skinny jeans with flat heel knee high boots as well..

[roniheels]

No really a challenge, but I am going to wear my thigh boots on the outside of my jeans more often in public. For those who don't or haven't worn them, thigh boots are so comfortable and feel so good on your legs.

[JeffB]

No really a challenge, but I am going to wear my thigh boots on the outside of my jeans more often in public. For those who don't or haven't worn them, thigh boots are so comfortable and feel so good on your legs.

Good for you! Just make sure your jeans are as snug as humanly possible which, along with the boots, makes for a smoother, sleeker profile.

[Dr. Shoe]

I don't set any challenges. I just dress the way I want. I would tuck the pants inside the boots, but my legs are so skinny, plus I don't have any skinny jeans. I would love to wear pumps with stockings and a skirt, but I don't look 100% like a girl so it won't work. I'm not into the crossdressing look. I just like to add heels to whatever I'm wearing. But, I find that heels look better with girls jeans, than with guys. Just my opinion.

The same here.

Me too!

Pants tucked in knee high boots with a low heel.

I like the look, and I'd like to try it.. I think first though, I'd like to try skinny jeans with a pair of ankle boots because I'm not to certain about myself in pumps..

A little off topic, but I'd like to try skinny jeans with flat heel knee high boots as well..

That's what I wear to work mainly except they're jodhpurs and not skinny jeans...

[SleekHeels]

I have only worn heels pretty consealed under long trousers before. I'd like to wear knee high boots with skinny jeans, something like the picture attached.

That's a great look dbert, very smart and stylish. For me the only thing missing is a black leather belt. A black v-neck jumper or a smart jacker might also be a good addition if you need something over the shirt when it's cold. Definitely a positive feel-good outfit. In the right surroundings I can imagine admiring looks and compliments.

First, there is no such thing as “just boots”.

Only "unjust boots" .... point taken !

[Alexis Hill]

Well a long standing challenge is I want to try to walk in some ballet heels. It not something I think I will do anytime soon since most stores don't have them where you can try them on. And I really don't want to buy them since I don't I will have much use for them.

[Gudulitooo]

For now my next challenge will be the court heels with skinny jeans look, which will be a step forwards from just boots.

Sleekheels,

Same here, this is how I proceed. Indeed, wearing courts under skinny jeans is also my next challenge but I have two problems : First I was deprived from exercice for 2 months because of a f....ing virus which resulted in a strange modification of my body shape (surprisingly larger at the waist....). So my skinny jeans will wait.

Second, Noël (thanksgiving) approaches this is not going to help.

I already wore black wedge courts with said skinny blue jeans (and black socks), the challenge is now to do that again. I don't if it is only me, but I find sometimes more challenging to wear an outfit for the second time (not talking about pain or misfit).

[hhboots]

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.

[Steve63130]

HHboots, I agree. Thighbootguy always said to look at yourself in the mirror before you go out in public to make sure you're happy with the image you present. In skinny jeans and stilettos, I would double up with laughter! Just not my style! Steve

[inquisitor]

Baby steps for me. Haven't tried any shoes on in public yet, but I have walked home from the bus a couple of times (down the alley) in a cheap pair. Working on longer walks in them. No daytime heeling yet. I've gotten buying them in public pretty well down.

[Histiletto]

My first yearnings were to have the look of wearing high stiletto heel pumps before realizing the effects that height increasements would add to the heeling experience. Yes, men also want to include stilettos with their choices of high heeled footwear. So wearing block heels hasn't been a priority, not that other heels haven't been considered at times. With this preference comes the realization that exposing my heels would be more controversial in the public environment, even in this forum of heelers who also consider the look to be extremely "feminine". This is a result of our social brainwashing and yes I have been infected also. This is one of the reasons public heeling activities is a lot harder for me, because I don't want to be viewed as a "want-a-be women". However, this perception will never change if I stayed dormantly private behind closed doors and under the cover of shadows/camouflage. So my next step is to wear shorter trousers/jeans/pants so that my stiletto pumps are more a part of my total look, instead of being noticed sightings by an opportuned glance or happenstance and introduce this look with more of the people I hang with, at least those I consider to have open minds.

[Gudulitooo]

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...

[Dr. Shoe]

Well a long standing challenge is I want to try to walk in some ballet heels. It not something I think I will do anytime soon since most stores don't have them where you can try them on. And I really don't want to buy them since I don't I will have much use for them.

There are two problems you will have. The first is finding a store that sells them and is prepared to let you try them on. The second is the fact that, unless you're an experienced wearer or have danced en pointe, you will bareley be able to stand up in them, let alone walk without many, many hours of practice. In fact you will probably find that they hurt to wear at first.

This is why any retailer that does sell them will not let you try them on on the premises.

[AZShoeNut]

Interestingly enough, another next challenge for me is to wear flats out. I have a pair of low heel/flats with a stacked wedge that is 1-inch or less tall. They are super loud. I love the shoes and would love to wear them out. For whatever reason I am more nervous wearing them out than I am wearing my blue satin 5.5-inch stilettos.

Best,

AZShoeNut

[Gudulitooo]

ok so yesterday I achieved a long time challenge : I wore my 2 inch black courts with thin heels (no wedge). I put them on in Brussel and did all the trip back home (Paris) in train / subway, wearing them with my suit (business trip). The train came to another platform at the last minute, and the cars were in disorder compared to the information on the platform. A great walk. I am not wearing heels higher than 2/3 inches due to my size (6'4). It was new for me as the courts are much more girly than my regular block heeled boots. Also It was a strange outfit because my courts are not so smart (you could say "cheap"), so very different from the rest of the outfit. My next challenge is in fact a very recursive one : spending more time shopping for clothes instead of shoes, to bring nice outfits....

[AZShoeNut]

Way to go Gudulitooo!

[Steve63130]

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