What's Your Next Challenge Wearing Heels?

[tightlevisandhhboots]

I would like to wear skinny jeans this year with my flashy 4.5" Jones Boots, but will have to drop a few pounds at the waist before I can pull off that look well. I like tight jeans, as my signature states, but having a belly hanging over the tight jeans ruins the look;-) TightLevisandHHBoots

[Kittyinboots]

What a great night I had, challenging myself to go to a sports bar in high heel boots.

 

Tonight there was a pay per view event (WWE Survivor Series) at a sports bar called Fox and Hound.  I usually go out with my wife to these events, but she stayed at home since it was too cold.  Since I was by myself I dared to go out in an all black outfit, a black dress shirt, tight black denim riding jeans, my vintage 80's knee high Italian black boots, 4" heels,  topped off with a slim fitting leather jacket.  

 

I was sitting comfortably in a lounge chair near the front of the big screens, just admiring the look and feel of my boots, crossing my legs on occasion to pose a bit. This sports bar was dimly lit, and just about everyone including me, were glued to the screens, paying attention to football or pro wrestling.  Needless to say, it was nice that hardly anyone paid attention to my boots.  I was the first one to leave after the event was over, just a few people saw me walk out in my boots, but nothing was said. I even stopped by to pump gas in heels.  All in all it was a great night.  I might even consider doing this again, wearing my blue riding jeans, to contrast my black boots.

[Heelster]

Skinny jeans and stiletto pumps - - - coming soon - 

[bluejay]

Thanks for your post, kitttyinboots. Sounds like you had fun.

 

This afternoon, I went out on a shopping trip to the Outlet Mall, wearing "Hue" medium wash leggings, black long length polo, black leather jacket and my knee boots, with 2-1/2" block heels. I got several comments on my look in the stores I visited, Payless, Naturalizer, Nine West and the  Izod store. I did buy a pair of blue strappy sandals on sale in Payless, with a 40% off rewards coupon, for wearing next summer, when sandal weather returns.

 

I had a nice time out in heels!

 

Happy Heeling,

bluejay

[pebblesf]

I would like to wear skinny jeans this year with my flashy 4.5" Jones Boots, but will have to drop a few pounds at the waist before I can pull off that look well. I like tight jeans, as my signature states, but having a belly hanging over the tight jeans ruins the look;-) TightLevisandHHBoots

Yeah buddy, I LOVE the tight levis/boots look as well.  I just picked up a pair of tight levis 511s from a thrift store, and was pleased that I don't look too bad in them...Wish my legs were a little more defined, and I too, could stand to lose a few pounds...Nonetheless, I dream of wearing these tight levis with my jessica simpson boots over them! 

What a great night I had, challenging myself to go to a sports bar in high heel boots.

 

Tonight there was a pay per view event (WWE Survivor Series) at a sports bar called Fox and Hound.  I usually go out with my wife to these events, but she stayed at home since it was too cold.  Since I was by myself I dared to go out in an all black outfit, a black dress shirt, tight black denim riding jeans, my vintage 80's knee high Italian black boots, 4" heels,  topped off with a slim fitting leather jacket.  

 

I was sitting comfortably in a lounge chair near the front of the big screens, just admiring the look and feel of my boots, crossing my legs on occasion to pose a bit. This sports bar was dimly lit, and just about everyone including me, were glued to the screens, paying attention to football or pro wrestling.  Needless to say, it was nice that hardly anyone paid attention to my boots.  I was the first one to leave after the event was over, just a few people saw me walk out in my boots, but nothing was said. I even stopped by to pump gas in heels.  All in all it was a great night.  I might even consider doing this again, wearing my blue riding jeans, to contrast my black boots.

Great job, that trip took alot of courage!  I would love to take a trip like that....

[PolarSun]

For me the biggest challenges (and also probably dreams) are following - be locked in my 6 inch locking heels for not known time (but this depends on if I find a tolerant girlfriend who will lock me) and be able to master higher heels, even maybe ballet ones 

[Kittyinboots]

Today was a great day with a big challenge.  Boots at the office.   This was our casual Friday, since we are off for Thanksgiving holiday.  I wore my tight fitting black denim riding jeans tucked in my tall black cowboy boots fully exposed.  Just a few looks, but people were mostly focusing on wrapping things up before our holiday.  I was not alone as several people tucked their jeans into their boots.  And several employees took off work today, which was my motivation to dare to wear boots.    I assumed that people still talked about me wearing boots, but I am fine with that.  My manager didn't think anything of it, since she has seen my boots before, and she wore her jeans over her black high heel boots. We were also allowed to leave early around 3pm. All in all, it was a very laid back day from a business standpoint.  But I will say that wearing boots at the office increased my courage for wearing my cowboy boots to about 97% confidence level.  Great day to go to work!

[HappyinHeels]

Kittyinboots,

 

I have heard the guys on WTMJ in Milwaukee talk about Fox and Hounds but didn't realize where else they had restaurants. Glad  you wore your boots to your workplace. Always nice to see our members' confidence rise as they explore new frontiers ("to boldly go where none of my heels have gone before") or something like that! Confidence is the key to success for sure. HappyinHeels

[w6ish]

i'm not sure what the next challenge is for me.  for starters i don't wear heels lower than 6 inches, i never cover any of my heel with pant leg length, i've worn my 6 inch heels and 7.5 inch heels with my ultra fun and super tight Bluenote skinny jeans all summer, worn my white 7.5 inch heels with Daisy Duke skin tight shorts in denim, rubber and pvc, sometimes with fishnets and sometimes bare legged, painted toe nails, kept my hair long to the small of my back, kept my waist at 30, walked the mall, the airport, the train station, the streets of the good cities of Ottawa, Montreal and Toronto from top to bottom, and places inbetween, wine and dined many elegant ladies in said outfits, wore black body suits with a blazer and my white 7.5 inch heels on steamy summer nights in said cities, through art galleries, museums, cultural places, exotic restaurants.  worn the black mini skirt with fish nets, bare legged, same with the skort, with high cut jackets and blazers.  i've managed to take care of myself well enough that there is no problem body wise above the belt, the problem is below the belt and how to hide my sexiness in my ultra tight skinny jeans. 

what i'm thinking, maybe its time to roll out some of my $$$ and attend these heel meets in other places in the world.  i've read with much interest these meetings in England and in the US, even had a few invites, and maybe i'll ask the lady if she'll cut me loose for a few weekends this coming year so i can meet up with you fellow hhplace posters, in person. 

i think that would be my next and biggest challenge.

[Steve63130]

You don't have to go alone to heel meets. I've attended several, both with the wife and solo, and others have, too. Significant others have always been welcome. It's a good chance to expose her to other SOs so she knows she's not alone, and expose her to guys who might be even more daring, so she can see you're not so bad after all! HA HA HA

 

 

Steve

[NewfieGuyInHeels]

I like most ppl have just started wearing my heeled boots with slim/straight jeans. They're hemmed just to the top of the heel so the whole foot/heel of my boots are on display. And I've been wearing my knee/thigh high flat boots over jeans for a couple years. So I guess for me I want to try pumps. Nothing open toe, I'm not big on open toe heels, just a preference, but for some reason going from a boot to a pump is a big hurtle for me. I just ordered http://www.callitspring.com/ca-eng/clearance/womens-shoes/heels/91569787-VAQUERANO/96 and plan on wearing them with bootleg jeans, a dress shirt (prolly red) and a black vest. As a side note I now regularly paint my nails and I'm gaining an interest in makeup.

[Black_Boots]

Setting goals is a clear way of progressing. Achieving your goal is also boosting your self confidence and lead you to setting more challenging goals!

 

My last challenge (Yesterday) was to travel to the US wearing my new pair of bootie Michael Antonio. I felt quite well walking in the airports, but the one hour queue for the US immigration was difficult... Walking in heels is easy, but wearing heels for a long time is a harder job!

 

When I look back a few year, I have made a nice improvment, through small challenges, and when I look at myself in the Mirror, I see a men in heels, but when I wear my heels, I feel comfortable.

For the moment, I feel well when I am not in my hometown... Definetly the most challenging goal is my coming out... Too challenging for the moment, I need to build up confidence!

 

 

[Heeleddude]

The only challenge for me is to go higher and higher. I just love the way my feet feel when they're arched.

[JeffB]

I guess my only challenge would be looking for new and different places to wear heels as that would keep things new and fresh for me.

[PolarSun]

The only challenge for me is to go higher and higher. I just love the way my feet feel when they're arched.

 

Fully understand, I have it the same, I love the feel as well. For now I do not wear any lower heels than 6 inch and want to go higher, including ballet boots.

[Heelster]

You don't have to go alone to heel meets. I've attended several, both with the wife and solo, and others have, too. Significant others have always been welcome. It's a good chance to expose her to other SOs so she knows she's not alone, and expose her to guys who might be even more daring, so she can see you're not so bad after all! HA HA HA

 

 

Steve

 

I scare my SO now - - Can't imagine anyone doing a better job of that. Ahhh - not to worry, she doesn't wear heels, and most likely wouldn't want to see what some of us wear when we are away.

.

[Matt010487]

Mine is definitely to get some skinny jeans and continue walking for longer. I've driven to a few towns recently away from where I live and just walked in my 4 inch black pumps. Got up to about an hour before my feet hurt too much

[mlroseplant]

I've met many challenges this year, psychologically speaking.  I started heeling publicly about 1.5 years ago with some 3.5 inch clog-type shoes, but I didn't get some seriously tall heels until about a year ago.  I can't yet say that I am completely comfortable wearing heels to every possible place one could imagine, but most places, I am.  I now wear 5" heels with a suit and tie to church, for example, something I never imagined I would do a year ago.  I am *still* waiting for someone to comment, but it hasn't happened yet. I have pushed the gender-bender envelope about as far as I want to (and surely as far as my wife wants me to), but I would really like to wear high heels with shorts next summer.  I'm still not sure how I'm going to pull that off, as it's difficult even for females, but it's in the back of my mind.

 

Another challenge I've set for myself is a purely athletic one--I want to be able to say I've walked 1,000 miles in heels.  So far, I've made it about 300 documented miles.  I try to walk about 2 miles a night, but I don't have the opportunity to walk every night.  I will say this, Vibram replacement heel tips are my friends.

[Steve63130]

mlroseplant,

 

Congrats on your progress. That is huge!

 

Wearing heels with shorts is fun if you select the right heels. I have worn all of these heeled clogs and sandals (2 to 3.5") in public with shorts (often with beige or tan pantyhose and always with a satin rose-copper colored pedicure). I've never had any stares or iDrops, but I have had some compliments from women. I don't wear anything with stiletto heels, or any over-the-top brightly colored shoes, or pumps with shorts, though.

 

You can do it, too! Let us hear from you when you do. Good luck!

 

Steve

 

 

[mlroseplant]

Thanks, Steve.  It does feel good to be pretty much totally relaxed about my choice of footwear, and most of the time, I feel like I'm wearing it well.  We all have our bad days, but I'm dialing in the "pattern."

 

Thanks for the suggestions on the shoes.  I can totally dig the second to the last sandal (black thong wedge sandal), and I already own something very similar to the last clog-type shoe.  In fact, that's the very sort of shoe that got me started a couple of years ago.  Well, more than a couple of years ago.  I've had a number of pairs like that for some time before I decided to take the plunge and get some truly "high" heels.

 

I must tell you, and everyone here as well, that I had such a negative reaction to the picture I posted on the "freestyle" thread of me in shorts and heels, that I may well just give up on the idea.  I mean if youse guys make fun of me (and I don't mean you personally, Steve), I can only imagine what the general public would have to say about it.  I dunno, maybe it really does look bad.  I can't help it.  I AM a white guy.  No hard feelings.

[Shafted]

 

I must tell you, and everyone here as well, that I had such a negative reaction to the picture I posted on the "freestyle" thread of me in shorts and heels, that I may well just give up on the idea.  I mean if youse guys make fun of me (and I don't mean you personally, Steve), I can only imagine what the general public would have to say about it.  I dunno, maybe it really does look bad.  I can't help it.  I AM a white guy.  No hard feelings.

Honestly here is not always easy to take, but it does good. I would want to know if what I was wearing looked like hell or not. I have no use for people who lie just to make me feel good. It serves no useful purpose.

[mlroseplant]

Honestly here is not always easy to take, but it does good. I would want to know if what I was wearing looked like hell or not. I have no use for people who lie just to make me feel good. It serves no useful purpose.

Yes. Which is exactly why I may well give up on the idea of shorts and heels. I would like to advance the idea that males can wear a little bit broader variety of styles. Yes, I've developed a thicker skin about giggles from groups of teenaged girls, but I will never pretend that I do not care at all what other people think. Ideally, I want other people to think, "Wow, that actually looks pretty good! I wonder if I (or my husband/boyfriend) could do that? " I know that's not going to happen too often, but it's a goal. Sometimes, there's a fine line between not giving a hoot and looking totally absurd. Thanks for your input, Shafted.

[Steve63130]

Mlroseplant,

 

I went back and looked at the pic you posted and the comments. There were comments on how pale your legs were in that photo, but there wasn't anything bad about the look of the shorts and heels together. In fact one person commented positively. Here is my take, for what it's worth:

 

It looks very feminine to me. The shorts are very short and the heels are very slender and high. They go well together, and you have a good figure for the outfit. If that's the look you want, go for it. There is nothing wrong with it - it looks fashionable. But you will definitely be freestyling. The fact that you're male might elicit a negative response in the form of giggles, laughter, finger pointing, etc. It IS out of the ordinary, after all, and that's the normal human response when the clothing we see on a guy doesn't fit into the pure masculine pigeon hole for which our brains are socially programmed. My guess is that not too many people will really notice, though. They're wrapped up in their own world, and they would have to notice that the person inside the clothes is a guy.

 

I personally would opt for a more androgynous look, with longer shorts (mid-thigh) with no cuffs, and less feminine shoes (such as I posted above). If your legs are truly that pale, some tan pantyhose would make them look better in my opinion. I'm much more comfortable with my more conservative shorts, pantyhose, and shoes (and more importantly, so is my wife).

 

Good luck.

 

Steve

[SleekHeels]

Yes. Which is exactly why I may well give up on the idea of shorts and heels. I would like to advance the idea that males can wear a little bit broader variety of styles. Yes, I've developed a thicker skin about giggles from groups of teenaged girls, but I will never pretend that I do not care at all what other people think. Ideally, I want other people to think, "Wow, that actually looks pretty good! I wonder if I (or my husband/boyfriend) could do that? " I know that's not going to happen too often, but it's a goal. Sometimes, there's a fine line between not giving a hoot and looking totally absurd. Thanks for your input, Shafted.

 

As guys in heels I agree that we walk a fine line in terms of social reaction... there are some who are torn between a fear of ridicule and a need for approval, there are others who have complete dismissal of other peoples views (I feel a poll coming on: http://www.hhplace.org/topic/22004-scale-of-confidence/ ). Sure we have to be a little thick-skinned sometimes but taking that too far can be very egocentric and out of touch.

 

The word "absurd" is tricky... if I'm wearing a perfectly nice pair of heels and the only absurdity is that I'm a guy then the absurdity is in people's prejudice. Likewise if I'm wearing a totally outrageous and extravagant look (assuming some level of decency), then what's the big deal, it's just individual expression. In any case maybe we should cherish absurdity rather than fear it.

[Heel-Lover]

Hi,

 

This probably sounds crazy but...

My goal is to wear a cocktail dress (l.b.d. or a l.r.d.) with coordinated accessories to a corporate event....as a guy. (ie. no wigs/ make-up etc).  

Obviously statement high heels would be essential.

This would throw the cat among the pigeons...

 

A year ago I was wearing skirts, and was keen to try a dress. Dresses turned out to be easier than skirts to coordinate once I got over the initial fear of them.

I had a bold challenge a year ago but it was surprising how easy and how empowering it was once I broke it.

 

I would hope to be able to bust through this new challenge this year, although I know it is a little more daring.

 

rgds

Heel-Lover

 

 

 

 

[mlroseplant]

If nothing else, this has sure made for an interesting discussion. Thanks again for all the thoughts and input.  Yes, Steve, my look in the Freestyle section was probably rather feminine, but then again I was using my 25 year old hottie (Asian female) cousin as inspiration for this outfit. Whether I'll actually ever wear such a get-up in public is still to be determined, but that's still several months out.

 

What I actually wound up doing last summer was wearing juniors' shorts, which I love, but it is really tricky to get the size right, especially once you put them through the wash a couple of times.  But I would always wear flat sandals, when what I really wanted to be wearing was heels.  I do have quite a number of longer shorts, and one of them is even approved by my 14 year old son, even though they are tight enough to require "tucking."  Maybe this particular pair, combined with some less radical heels could work.

[Heel-Lover]

Hi mlroseplant,

 

I have read your comments on the outfit you had concerns about, white short shorts, hosiery and heels.

 

Firstly you have a good figure so you can wear that look just fine.

Next it looks as though you had sheer pale hosiery on (not opaques), which means you wax/shave your legs?

 

I too have very pale complexion but I choose not to worry about it and I deal with it by using spray tan or...using traditional black/white pairings in what I wear.

 

For instance I would wear the same outfit you had (and truly do) but with slight differences...

1. Go bare legged (it looks as though you had sheer hosiery on, not opaques, which suggests you groom your legs? - if so bare them

2. Try a basic black stiletto pump - the classic profile looks awesome - go quite high if you're up to it - or you could still rock the wedges

3. Try black short shorts instead - dark colour will also mask underwear which can show through white garments...

4. Try a very fitted top (cap sleeved) - even try a bold colour that suits you such as royal blue, or neon pink?

5. Add some coordinated items - black bag. black watch, black cuff, a black hat etc.... to tie in with the shoes

 

cheers

Heel-Lover

[mlroseplant]

Hi mlroseplant,

 

I have read your comments on the outfit you had concerns about, white short shorts, hosiery and heels.

 

Firstly you have a good figure so you can wear that look just fine.

Next it looks as though you had sheer pale hosiery on (not opaques), which means you wax/shave your legs?

 

I too have very pale complexion but I choose not to worry about it and I deal with it by using spray tan or...using traditional black/white pairings in what I wear.

 

For instance I would wear the same outfit you had (and truly do) but with slight differences...

1. Go bare legged (it looks as though you had sheer hosiery on, not opaques, which suggests you groom your legs? - if so bare them

2. Try a basic black stiletto pump - the classic profile looks awesome - go quite high if you're up to it - or you could still rock the wedges

3. Try black short shorts instead - dark colour will also mask underwear which can show through white garments...

4. Try a very fitted top (cap sleeved) - even try a bold colour that suits you such as royal blue, or neon pink?

5. Add some coordinated items - black bag. black watch, black cuff, a black hat etc.... to tie in with the shoes

 

cheers

Heel-Lover

Thanks for the input, H-L.  Just for the record, I am not wearing any type of hosiery in this photo, or any other.  That's because I have never even tried on any type of hosiery other than ordinary men's socks in my life! I did start shaving my legs last spring.  I just think it looks better with the short shorts. My wife does not necessarily agree with that opinion.  I do have a black pair of shorts almost exactly like the white ones in the photo.

 

The tanning issue actually could be a problem depending upon my job, because if I'm working outside, my arms, neck and face will become fairly dark (after turning red, haha), but since I'm required to wear long pants and boots, my legs of course are unmolested by the sun.  At least I don't have flip-flop tan.  THAT I couldn't tolerate, LOL. 

[jim102]

DEALING WITH FATHER! Dealing with hell and lucifer!

[Matt010487]

Hi all, a few weeks back I posted saying that my next challenge was to get some skinny jeans and wear them with my heels. I've since bought some skinny jeans and I've been wearing them at home a lot although not out too much. Ive attached a few photos so take a look and see what you think. I'm going to try and wear the more often in public and pay for gas and a few things like that whilst wearing my heels and jeans. I've done it once thus far and it was great so I shall be out and about more often from now on....