Positive First Reactions & Grown Confidence

[BootBoy09]

Hi all,

I've been reading on the forums for over a year now, and I thought I might as well introduce myself. I have been posting little tidbits here and there but now I would like to share with you my experiences last week. It was all of your guys posts that I was able to do this and gain confidence in myself.

I have been street-heeling on and off for almost a year now. Mainly about 5 times a month I would venture out in my boots underneath khakis or jeans. But now I am doing it more frequently, and receiving my first positive comments.

The only people who really know is my wife and my one of my best friends, who's a fashion merchadiser graduate. But I felt I needed to move on to the next level. My wife keeps telling and encouraging me to wear my heels more often as I look very classy and stylish in them, and it really separates me from the other drab male fashions. My fashion merch. friend, Julie, she accepts it fully and we share the same shoe size (womens 10), she enjoys trying on my collection as I do of hers. I have wore them out to malls, restaurants, movies, museums, and parks, but I have never received a look, glance, or comment about my footwear.

Last week I wore my 2.75" chunky heeled black boots underneath long blue jeans and a black shirt to work. I work with people who's mostly in their mid to late 20's so its a younger atmosphere. I usually wear to work are just sweats and sneakers to stay comfy as it is a physical fast-paced job, but on Saturdays, its usually relaxed.

Here are some pics of what I wore to work that day -

Those are currently my street-heeling boots, until I gain more confidence and wear high heeled shoes.

When I walked into work looking like that, no one noticed of my attire. It wasn't until we got coffee and McDonalds breakfast in all of us until they started to notice me. First thing they saw was me wearing jeans, I never wear jeans to work! They all said I look very good in them. The first reaction to my boots was to the girl tech, she was like "Oooooh shiny shoes!", I replied "Heck yeah, everyone's gotta have shiny shoes". She smiled and went back to her work. The driver/storesman saw me walking by and he glanced down at my feet a couple times, as it was a different look for me. He said "Wow, dress shoes huh?", I replied "Yeah gotta look good to go out after work to watch the game!". Then after we talked about the upcoming hockey game.

It wasn't until I was sitting down at my workbench having my lunch, that I got a surprised reaction. In the pictures, you can see that when I stand up the jeans covers the heel so all you see is the toe portion of the boots, but when I sit down, you can clearly see my heeled boots. My partner came in and immediately notices saying "Whoa! Are those high heels?? Why the heck are you wearing high heels, are you crossdressing or something!?". At that time I didn't feel nervous, I simply replied "They're just heeled boots like cowboy boots, it looks good, its now the upcoming fashion trend! A lot of the popular designers now make heeled shoes for males, plus it makes me stand out! Especially to the chicks!". From there, he pretty much shut up and went whatever and carried on with his work.

My boss walked by me as I was working, he looked down at my boots and went "Hey those are some nice kicks, you look good today!". My partner quickly blurted out in immaturity saying "Hey look again he's wearing heels, lift up your pant leg and show him!", as he was trying to bring me down and mock me. I pulled up my pant leg exposing the heel, and my boss shrugged his shoulders and said "He still looks good" and carried on. I just laughed silently to myself that my partner was trying to make fun of me but he was just making himself look stupid to others, from there my confidence went higher. For the rest of the day, it was work as usual, everything went well.

Its just funny how things play out. I came into work expecting the worse, I was going to mocked among my co-workers, but it turns out that I do look good that day, and everybody gave me postive comments about it, well mostly everybody hahahaha!

For sure now I'm going to try on other higher heeled shoes with different clothing combination while still looking good. It was all in my head that I was expecting negative comments, but in reality once you're actually out there doing it, the public doesn't usually notice, or don't care. A lot of them it seems like they accept it and its part of the fashion trend.

I give many thanks to this forum and its member's stories of their street-heeling experiences. I feel much better about myself and that I'm not alone at all. I'll continue to be more active and get to know all of you guys and girls and also share with you my photos and stories.

Thanks for reading!

BootBoy09

[JeffB]

An excellent first step, BootBoy09! We all have to start somewhere, and your outfit looked good for your first attempt. Now that you've got that first experience under your belt, it'll progressively become easier from there. Keep it up!

[Thighbootguy]

BootBoy09 -

What a good outting at work. I have an aunt who keeps reminding me "quality work takes time". JeffB is right, it gets easier each time you go out and it sounds like you have a good support team.

I would suggest you try leather boots for all day wear. I find them more comfortable.

Enjoy your heels.

[canadianbeaver17]

Hey good work man..(or boy..lol). Those are some nice boots. I started out with a pair of wedge loafers about the height of your boots. I wore them to school a couple times and got similar reactions to yours. Most say "nice girl shoes" and more on. Others just think they are normal boots. Even if one makes a big deal (such as your partner at work), others will come in and shit them up. I had a situation sitting in the cafeteria at school with my wedge complete exposed. One girl was like "WTF?". Her friend piped up and said "hey, they look pretty good on him, so what?". That quickly shut up the first girl. lol I think chunker heels like yours are a good start. That's what I wear if I go to school and want to wear chic shoes (unless they are flats and could pass for unisex). I wouldn't wear stilettos to school....but never say never.

[flavio]

All I have to say to BootBoy09 is CONGRATULATIONS in your first day heeling at the office! Heels for all! Flavio.

[micha]

Boot boy, my congratulations too As freelancer I'm always a little precautious with wearing heels at work. But I have a problem with my lip ring. It's difficult to get the ring in again after several hours. Hence I dared to visite a customer wearing my lip ring. There was only a short debate "Doesn't it disturb while eating?". I answered truly "If it were in the mid of my lip, you might be right but on the left side it's no problem". I never earned any comment about my 2.5'' cowboy boots. Or should I better say cowgirl boots? Last month I got a call from the boss of the company: He said "Hi, Michaela!". We both were laughing loudly Obviously my outfit had been noticed. I sent back my program update undersigned with "your michaela" nice greetings micha(ela )

[bluetango]

Bootboy09, An altogether excellent first outing. I think your choice of a low, chunky heel was excellent. The style you picked is actually quite masculine (as if one could define what that is). Let's just say it is not "too" fashionable. It was interesting that your wise-acre partner tried to make fun of you and others, like your boss, put him in his place. It is nice to see that others agree that rudeness is rude. (Am I good with the obvious or what?) I street heel more and more, but don't heel at work. There are some real jerks there and I just don't the hassle of dealing with them. My street heels are all fairly chunky and I think that helps with acceptance. I never get comments - I have grey hair and people respect grey hair! LOL! Keep heelin' Bluetango, who owns almost nothing blue

[BootBoy09]

Wow! Thanks for the warm reception guys! The people I work with are pretty good, easy to get along with, we're a tight knit company. They all know me and my family/friends pretty well, we often have company events that help gel the company together. It really helped with my confidence when people do recognize and compliment on your style. I agree that there are some real jerks out there in the world who wants to ruin it for you, but you know what, I'm ready for that. I could care less if a stranger says something to me to bring me down. Heck I'd just laugh and carry on with my business. If i'm comfortable of who I am and it shows on the outside, people will respect that. As long as I have supportive family/friends and the members of this board, nothing will really phase me if a negative comment is thrown. I'll have to do some shopping for some higher heeled boots to bring me to the next level of street-heeling. I've done pretty well with my boots now, so maybe something in the 3 - 3.5" range? Can anyone recommend any styles of boots I should move on to that I can street-heel in and still look good? Maybe different styles of pants instead of jeans?

[Shafted]

The nice thing, BootBoy09, is that the jerks are in the minority. If they mouth off too much, it's usually them that come off looking like idiots to the rest of the world. Enjoy.

[iloveboots]

Great pics and article. The Boots look great and your handling of your work situations was fantastic. Look forward to chatting and possibly connecting....time to go to the next level and show of your great Boots more! A visit to the Oasis Restaurant will do the trick.

Your BC Boot friend,

david

Hi all,

I've been reading on the forums for over a year now, and I thought I might as well introduce myself. I have been posting little tidbits here and there but now I would like to share with you my experiences last week. It was all of your guys posts that I was able to do this and gain confidence in myself.

I have been street-heeling on and off for almost a year now. Mainly about 5 times a month I would venture out in my boots underneath khakis or jeans. But now I am doing it more frequently, and receiving my first positive comments.

The only people who really know is my wife and my one of my best friends, who's a fashion merchadiser graduate. But I felt I needed to move on to the next level. My wife keeps telling and encouraging me to wear my heels more often as I look very classy and stylish in them, and it really separates me from the other drab male fashions. My fashion merch. friend, Julie, she accepts it fully and we share the same shoe size (womens 10), she enjoys trying on my collection as I do of hers. I have wore them out to malls, restaurants, movies, museums, and parks, but I have never received a look, glance, or comment about my footwear.

Last week I wore my 2.75" chunky heeled black boots underneath long blue jeans and a black shirt to work. I work with people who's mostly in their mid to late 20's so its a younger atmosphere. I usually wear to work are just sweats and sneakers to stay comfy as it is a physical fast-paced job, but on Saturdays, its usually relaxed.

Here are some pics of what I wore to work that day -

Those are currently my street-heeling boots, until I gain more confidence and wear high heeled shoes.

When I walked into work looking like that, no one noticed of my attire. It wasn't until we got coffee and McDonalds breakfast in all of us until they started to notice me. First thing they saw was me wearing jeans, I never wear jeans to work! They all said I look very good in them. The first reaction to my boots was to the girl tech, she was like "Oooooh shiny shoes!", I replied "Heck yeah, everyone's gotta have shiny shoes". She smiled and went back to her work. The driver/storesman saw me walking by and he glanced down at my feet a couple times, as it was a different look for me. He said "Wow, dress shoes huh?", I replied "Yeah gotta look good to go out after work to watch the game!". Then after we talked about the upcoming hockey game.

It wasn't until I was sitting down at my workbench having my lunch, that I got a surprised reaction. In the pictures, you can see that when I stand up the jeans covers the heel so all you see is the toe portion of the boots, but when I sit down, you can clearly see my heeled boots. My partner came in and immediately notices saying "Whoa! Are those high heels?? Why the heck are you wearing high heels, are you crossdressing or something!?". At that time I didn't feel nervous, I simply replied "They're just heeled boots like cowboy boots, it looks good, its now the upcoming fashion trend! A lot of the popular designers now make heeled shoes for males, plus it makes me stand out! Especially to the chicks!". From there, he pretty much shut up and went whatever and carried on with his work.

My boss walked by me as I was working, he looked down at my boots and went "Hey those are some nice kicks, you look good today!". My partner quickly blurted out in immaturity saying "Hey look again he's wearing heels, lift up your pant leg and show him!", as he was trying to bring me down and mock me. I pulled up my pant leg exposing the heel, and my boss shrugged his shoulders and said "He still looks good" and carried on. I just laughed silently to myself that my partner was trying to make fun of me but he was just making himself look stupid to others, from there my confidence went higher. For the rest of the day, it was work as usual, everything went well.

Its just funny how things play out. I came into work expecting the worse, I was going to mocked among my co-workers, but it turns out that I do look good that day, and everybody gave me postive comments about it, well mostly everybody hahahaha!

For sure now I'm going to try on other higher heeled shoes with different clothing combination while still looking good. It was all in my head that I was expecting negative comments, but in reality once you're actually out there doing it, the public doesn't usually notice, or don't care. A lot of them it seems like they accept it and its part of the fashion trend.

I give many thanks to this forum and its member's stories of their street-heeling experiences. I feel much better about myself and that I'm not alone at all. I'll continue to be more active and get to know all of you guys and girls and also share with you my photos and stories.

Thanks for reading!

BootBoy09

[Dawn HH]

Bootboy09:-) Congrats! You did very well at your first time wearing boots into work and on the job. Now since you broke the ice, you might be able to stretch the envelope a bit more. Those boots in the pics should be able to be worn anywhere and at any time. Cheers--- Dawn HH

[terayon]

wow, great story man congratulations on wearing your boots to work. I only wish I'll ever have the confidence to do that. Those are really nice boots and should be fine to wear anytime.

[BootBoy09]

Iloveboots: Thanks for the reply man! Yeah for sure we'll chat and possibly connecting later on. It's my first anniverary with my wife and she just got me a new pair of 4" stilletto knee high pointy boots from Aldo, was sure a real nice surprise when I got home! As for the Oasis restaurant, i'll have to go there sometime on my days off (whenever that is...). Dawn HH: Yeah ever since I wore them to work, i feel much more comfortable about it and I don't mind if some of my friends know about it because its still me. For sure I am able to wear them more often now and just realize its just something to add to my attire. Hopefully I can graduate onto bigger/daring ventures later on. Terayon: Thanks for the comment. For me, I was very cautious about my streetheeling, like it would race in my mind if i could do it or not, and end up chickening out. Sometimes you just gotta do it, and just have fun with it. My advice is to take baby-steps, work your way up. Like walk around the block in your heels or walk around the park at night (where its safe of course), and then work your way up I find it very helpful to read the other posts about their streetheeling experiences, knowing that there are a great number of people who are very accepting of it. Heck i just found out today my wife just told one of our friends that I was into womens shoes and she was totally cool with it and wants to go heeling with me sometime! Thanks everyone for the encouragement, I'll keep you updated on my future experiences!

[iloveboots]

Very Cool...what a great gift! Happy Anniversary. Let me know what you think of the Oasis after you check it out. There is parking at the back of the restaurant on Thurloe, just need to have a note put in the window from the restaurant that gives you 2 hours free,

david

Iloveboots:

Thanks for the reply man! Yeah for sure we'll chat and possibly connecting later on. It's my first anniverary with my wife and she just got me a new pair of 4" stilletto knee high pointy boots from Aldo, was sure a real nice surprise when I got home! As for the Oasis restaurant, i'll have to go there sometime on my days off (whenever that is...).

Dawn HH:

Yeah ever since I wore them to work, i feel much more comfortable about it and I don't mind if some of my friends know about it because its still me. For sure I am able to wear them more often now and just realize its just something to add to my attire. Hopefully I can graduate onto bigger/daring ventures later on.

Terayon:

Thanks for the comment. For me, I was very cautious about my streetheeling, like it would race in my mind if i could do it or not, and end up chickening out. Sometimes you just gotta do it, and just have fun with it. My advice is to take baby-steps, work your way up. Like walk around the block in your heels or walk around the park at night (where its safe of course), and then work your way up

I find it very helpful to read the other posts about their streetheeling experiences, knowing that there are a great number of people who are very accepting of it. Heck i just found out today my wife just told one of our friends that I was into womens shoes and she was totally cool with it and wants to go heeling with me sometime!

Thanks everyone for the encouragement, I'll keep you updated on my future experiences!

[Dawn HH]

BootBoy09:-) That's the greatest Anniversary gift that your wife could have given you. Congrats! Cheers--- Dawn HH

[BootBoy09]

Here's another update from me! As my confidence grew, I graduated to a new pair boots to streetheel to!

They are my black leather knee-high boots from Anne Smith i got off ebay a few weeks back. They are extremely comfortable boots, even more so than my first ones. They are way more feminine looking and its quite the jump from the boots i had before.

A couple days ago me and my wife decided to go out to a fancy italian restaurant for our anniversary. We both dressed up nicely, and she wore her knee high stretchy pleather like boots with a 2-inch heel, so we both celebrated with our boots on! It was quite fun!

At first I was nervous heading inside plus we had a 20min waiting period for a table, so we had to stand around with other customers. You can definately tell I was wearing feminine boots but it seems like no one really notices or really cared. I didn't get any funny looks or comments, I was just being normal me as always. There a few people around our table when we were seated, but that wasn't a problem at all. When I am seated it shows more of the boots and heel. Still no one really notices or cares!!

I'm really beginning to enjoy streetheeling, its very exhilarating experience!

Here are some pics of my new boots.

[JeffB]

BootBoy09: Congrats on a great experience you shared with your wife. As you've just learned, a little confidence certainly goes a long way! And the boots look nice too. More power to you, my friend!

[Thighbootguy]

BootBoy09 - Sounds like you had a fun outing with your wife. JeffB says “a little confidence certainly goes a long way” and he is absolutely right. As you keep going out you will find that your confidence will grow and that a lot of confidence goes even further. Your right, most people don’t notice and if they do, they don’t care. When your confidence get up to it, try wearing the boots over your jeans. One - the style looks great, and two - you don’t have to worry about whether someone sees your boots or not. The whole paranoia about “did anyone notice” goes away. The hardest step is getting out of the car but if your comfortable with the look no one else will care.

[Mickey S.]

I got similar boots like BootBoy09:

This is the picture as it appeared on eBay in the auction I won. I've worn the boots to work already and - according to my reflections in the glass-doors - they are / were (quite) visible when walking. Folks must have noticed but didn't say a word.

Currently these are my shoes I wear on a daily base:

CU!

-Mike

[Danielinheels]

Can anyone recommend any styles of boots I should move on to that I can street-heel in and still look good? Maybe different styles of pants instead of jeans?

Looking over at my avatar, you can see that I'm actually wearing a suit with those heels (for the record, that's just a pose in my old living room - never had a job where I had to wear a suit).

Certainly slacks could work, but that depends on how conspicuous you want to remain. Clearly in that picture I didn't care about how much of the shoe was showing, but a longer slack (or perhaps one with the cuffs let out) would suffice.

For fun's sake here's another shot of those shoes:

[iloveboots]

Awesome experience.....best part was "it was quite fun!" That's what it's all about, you two had a wonderful, positive time....

Just imagine next time!!!!

david

Here's another update from me! As my confidence grew, I graduated to a new pair boots to streetheel to!

They are my black leather knee-high boots from Anne Smith i got off ebay a few weeks back. They are extremely comfortable boots, even more so than my first ones. They are way more feminine looking and its quite the jump from the boots i had before.

A couple days ago me and my wife decided to go out to a fancy italian restaurant for our anniversary. We both dressed up nicely, and she wore her knee high stretchy pleather like boots with a 2-inch heel, so we both celebrated with our boots on! It was quite fun!

At first I was nervous heading inside plus we had a 20min waiting period for a table, so we had to stand around with other customers. You can definately tell I was wearing feminine boots but it seems like no one really notices or really cared. I didn't get any funny looks or comments, I was just being normal me as always. There a few people around our table when we were seated, but that wasn't a problem at all. When I am seated it shows more of the boots and heel. Still no one really notices or cares!!

I'm really beginning to enjoy streetheeling, its very exhilarating experience!

Here are some pics of my new boots.