I Think I'm Going to Take the Plunge

[SandalFan]

No matter how hard I try, I can't seem to stay away from this board, because every time I read these threads, I invariably wind up with an overwhelming desire to try public heeling myself. You street heelers have shared a lot of annoyingly inspiring experiences, and I'm growing weary of restricting my own heel-wearing to the privacy of my house. And now, thanks to you, I think I'm finally going to take the plunge myself.

However, unlike those of you who started out short, I'm going to start tall. I absolutely hate chunky heels, and don't like wearing anything shorter than 4". I can walk really well in 4" stilettos. My wife has even told me I have quite the strut when I wear my heels around the house (grin).

Unfortunately, my small collection consists entirely of sexy, dainty, open-toe pumps and sandals that I would never be caught dead wearing outside. I love ankle boots though, and briefly owned a pair of 5" stilettos, several years ago, but threw them out due to their poor quality. So, I did some quick shopping online and, as luck would have it, just found these Victorian-style Raven Platform Lace-Up boots at Payless.com:

http://tinyurl.com/3tw83u

4" stiletto with a 1/2" platform, functional laces, and a side zipper. Perfect!

I'm going to drive down to my local branch tomorrow morning and see if they have any regular size 10's in stock. Hell, I might even try them on while I'm there! If the clerk asks, I'll just tell her the truth - that I've grown bored with men's shoes and want to try something really different.

I've lived in the Midwest all my life, and have only seen a handful of guys in heels - but who were also in drag - so this should be interesting.

Wish me luck!

[HappyFeat]

Well, I for one congratulate you on your decision and confidence and hope you have an excellent first experience. However, I am looking forward to hearing your story of how it goes! Most of all, just have fun. Good luck!

[roniheels]

SandalFan... Good luck on your public heeling. But most of all have fun doing it. The first time is scary, exciting, and a major thrill ride. I have worn high heels in public for years and every experience is always fun and exciting. And don't be afraid to try on the hgih heels in the stores. Most of the clerks will even help you with your selection. Best wishes to you.

[onyourtoes]

Boots are a good way to break the 'going public' ice. A woman at work summed it up best when she looked down and said, "Are you wearing high heels?! Oh, they're boots." Payless clerks are very heel friendly to men. Perhaps it's in their training. All the stores have nearly every style stocked in 10. If they don't and they're not too busy, they'll check stock at other nearby stores. You can also call and ask. I had seen those boots on their site, but they really didn't jump out at me until you singled them out. I might try a pair myself.

[LovesHiHeels]

Good luck on your first trip out in heels.

[c_heels]

Had to look a little bit to find the boots you were talking about, but they are definitely very nice! I really like them also. I may have to go to Payless, they have a few new styles I really like. Those Seem like a great choice for a first try at street heeling. Good luck, and let us know how it goes!

[Bubba136]

Nothing like jumping directly into the deep end if you're determined to dive into the water. It takes a lot of courage to wear heels in public. And, while the fear is mainly locked in your own mind, it would help if your wife, or another female person, was with you on your first outing. Not only for support but people that notice your heels and see a woman with you, will not be as judgmental towards your appearance. Good luck and we expect a full report covering all aspects of your first heeling experience.

[jwhite44]

These are the same boots I talked about buying in a different thread! I also like them for all the reasons you stated. I'm about to order mine (ship to store), as I need to order a sz13, which I'm not going to find in stock. I did see a smaller-size in a Payless that I was in, they look nice. I'm keeping my fingers crossed on them, as I'm a male sz 12.5, and these boots (particularly the toebox) don't look especially generous space-wise. I'm hoping I'm wrong. Good luck in your search for them. Ship to store advertises a 2wk delivery time, so you might have your pair before mine. On a semi-related note, it would be nice if Payless had an inventory control system which allowed you to select a particular shoe, and then have it show you local availability. Especially for larger (13) sizes, it would be a great to see if any local stores actually stocked the shoe you're interested in.

[johnieheel]

I think you will find there is nothing to fear but fear it self Sandalfan. Just be your self and act as you would out in "mens" shoes. Most people won't even care and the .5% that do, don't matter any way. Good luck and fun heeling.

[JeffB]

SandalFan: As others have already said, the very first time out in heels is always the hardest, but once you discover just how easy it really is, you'll invariably wish you had done it long ago. Good luck to you!

[SandalFan]

Shortly after posting my first message, I started feeling anxious, followed by a case of the butterflies. The more the evening wore on, the more anxious I felt. I finally hit the sack at around 4am, and woke up at around 10 this morning. I haven't shaved in a week, and had run out of clean clothes, so the first thing I did was clean up and wash my clothes. This is where it started getting interesting for me. I have the weekend off, and normally just throw on whatever smells cleanest so that I can kick back and relax. Today, I was going to wear heels in public, for the first time in my life, and there was something very unsettling about the thought of how people would perceive a scruffy looking, smelly, 37-year old man wearing 4" stilettos. I was not about to risk creating a really uncomfortable situation. Bubba suggested I bring my wife for my first outing. Unfortunately, she's been homebound for the last 9 years, and it's unlikely she will ever be able to share my experiences with me. This morning, she asked me to go to the grocery store and pick up some lunch for her. My first thought was, "Wow, what better place to experiment at. A grocery store. In broad daylight. On a Saturday afternoon. Talk about ballsy." That's when I knew I was going to stop at Payless, first. Once at Payless, I tried to make a b-line to the Women's section, but diverted to the Men's section when I saw a woman looking for her kid. While there, I casually feigned interest in the men's shoes while I waited for the woman to leave, and then walked right over to the women's size 10's. To my very pleasant surprise, they had the boots. Knowing I'd change my mind if I hesitated for even a moment, I took one of them out of the box and tried them on. I just kept telling myself, "I know why I'm here. I know what I want to do, and I'm going to do it. Nothing else matters." It's a good thing I tried them on in the store, too. I discovered the 10's were too small. I was disappointed, but I refused to give up. Instead, I found a pair of 11's. Much better! I was surprised to see that my pant legs leave much of the heels exposed, so anyone looking at my feet knows instantly that I'm wearing stilettos. No matter. The clerk didn't even bat an eye as she rang me up. She simply asked if I'd found what I was looking for. I confidently replied, "Yup," and we completed the transaction. Back in my car, I swapped my biker boots for my new ankle boots, and experienced the strangest, most thrilling sensation I've had in years - heels against a gas pedal. Since my feet were already pointed due to the heels, they felt even more stretched when I reached for the pedal. I made it to the grocery store without incident, but the drive definitely felt a lot more awkward. I like to try and conserve fuel whenever possible, so when I visit a store that has a large parking lot, I like to park as far away from the entrance as possible. It saves me money on gas by not wandering around looking for an empty space, and is a terrific excuse for a bit of exercise. I arrived at the grocery store and parked on the back end of the lot. Suffice it to say, the place was packed. I spent the next 5 minutes mustering the courage just to get out of my car. Taking that first step was like taking a stage for a performance, though the last time I was on stage for anything was during my 6th grand band recital, and instead of knowing there was an audience there to see me perform, I thought that I was going to feel like all eyes would be on me while I shopped. Reality proved entirely different. The fact is, once I stepped out of the car, I was in my own world. Sure, I noticed everyone else, and quite a few people definitely noticed me, I just didn't care. I felt confident, and I projected that confidence in every step I took. I own these boots, and I walked like I belong in them. And no one said a single word. Unfortunately, by the time I was done there, my feet were killing me. I've never walked that much in heels. So, I when I got back in my car, I put my biker boots back on to give my feet some rest, picked up something else for my wife at the convenience store, put my new heels back on once I was done there, and returned home, where I told my wife about my experience. The feelings I experienced while street-heeling for the first time are nearly indescribable. The words 'exhilarating', 'exciting', 'fantastic', and the phrase 'scary as hell' come to mind, but they don't remotely do my feelings justice. For the first time in my life, I feel completely liberated, fashion-wise. For as long as I've loved heels, I've always insisted on restricting myself to wearing them in my house while admiring women who wear them in public. Until today, I had no idea how fun (or painful - grin) they truly are. One thing I learned is that street-heeling is definitely a head game you play with yourself. You have to be able to own the moment. You have to look and feel confident - like you belong in heels - if you want to have any hope of pulling it off. I also think wearing matching attire is extremely important. My entire wardrobe is black jeans and T-shirts, so these boots will perfectly match anything I wear with them. Shortly after returning home, I discovered I'd bought the wrong kind of cheese, so I went down to another store to find the right kind. Same experience as the other store. If anyone noticed, no one said anything, though I've no doubt that anyone within earshot heard me. lol As much fun as today's outing was, I don't think I'm going to try and make a daily routine out of it, and I definitely won't wear them to work. I had a lot of fun today, but I also know feet weren't meant to be elevated on a daily basis. You can do a lot of damage to them if you're not careful, and I'm still going to prefer the comfort of my biker boots to my new ankle boots most of the time. I'm just really, really happy that my first outing went as well as it did, and I'm absolutely ecstatic about the prospect of doing it again. And with that, here's a pic. Keep in mind, when looking at this, that I'm not holding my pant leg up. This is how much of the heels my pants really expose. hehehe

[dubheii]

Great story! And the boots look really good with the black jeans. Thanks for sharing!

[secondtake20]

Sandalfan; That is the same boot that I am going to get next month. They look good in your picture. Way to go, don't let your nerves get to you.

[loswabs]

Congratulations SandalFan, love them boots too

[Bubba136]

Congratulations, Sandalfan. Great first outing. I don't remember much about my first time out in heels. It was many years ago. But I do remember the rush it gave me to just realize that "hey world, here I am, high heels and all, for all to see." It does get easier but the thrill for me is still there.. (By the way, I am sorry to hear that your wife is homebound. I personally appreciate that you are being a good husband and taking great care of her. In sickness and health. That's what the words in the vows are.)

[jwhite44]

Just a phenominal account of your day! I don't know if the fact that we both like the same boots (I placed an order for mine online a few hours ago), but when I saw the beginning of your post, I had similar emotions - excitement coupled with butterflies. I'm definitely jealous that you were able to walk into a Payless and find exactly what you wanted. I know the thrill I had buying two pairs last week at one near me, and they weren't even the shoes I was looking for. I wasn't brave enough to try them on in the store, that takes real conviction. I wimped out for the 'buy & try (at home)" approach. However like you, I was also lucky to get a Payless salesgirl who was nothing less than professional. Definitely avoids what otherwise could be an awkward situation. I'm stuck waiting for mine to be shipped to the store (though I had a discount code I used, so maybe that's some consolation). I'm a little saddened that the 10's were too small (the size most of your others woman's shoes are?), and you had to move up to the 11's. That doesn't bode well for me and my 13's (but that's my problem). The picture you posted, I'm speechless. It's easy to see why I've always been drawn to these type of ankle boots, they look fantastic. Any other pictures you want to post, I'd enjoy looking at them. Not to tell you to back off after such an impressive first outing, but if you want to reduce the anxiety a little on subsequent outings, maybe a ~3" longer length pair of jeans, with a 'boot' cut, might be an excellent pairing with the boots. That should greatly reduce the amount of heel showing, which could minimize any extra attention you might get. That at least gives you more time to acclimate to being in 4" heels outdoors without having any self-conscious feelings about them. Definitely looking forward to details of your next outing...

[SandalFan]

It does get easier but the thrill for me is still there..

Funny you should say that. When I went to the other grocery store, I didn't hesitate for a moment to get out of my car. I just figured, "Well, I've already done it once and nothing bad happened. Let's do it again!"

I still felt anxious, but nowhere near on the level that had initially kept me in my car at the other store.

By the way, I am sorry to hear that your wife is homebound.

Thanks. It's been tough, but she's worth it. We'll be celebrating our 14th anniversary next month.

I wasn't brave enough to try them on in the store, that takes real conviction.

I normally only shop online, but I figured, if I'm going to wear them in public, I may as well try them on in public. Besides, since I was buying them in the store anyway, I wanted to walk out with the right size rather than have to go back later for an exchange.

I'm a little saddened that the 10's were too small (the size most of your others woman's shoes are?), and you had to move up to the 11's.

Yeah, that really surprised me. All of my other shoes are 10's. I was able to get my feet all the way into the boots, zip them up and tie them off, but my toes had zero wiggle room, and that's never a good thing. The 11's look and feel great though, so it's all good.

BTW: The side zipper? Uber convenient! Just pull down and slip off!

The picture you posted, I'm speechless. It's easy to see why I've always been drawn to these type of ankle boots, they look fantastic. Any other pictures you want to post, I'd enjoy looking at them.

Thank you. I'll more than likely be taking more.

Not to tell you to back off after such an impressive first outing, but if you want to reduce the anxiety a little on subsequent outings...

I appreciate the thought, but I was more surprised than concerned. I really don't mind so much of the heel showing. In fact, I rather like it. I just thought my pant legs would cover them more. Apparently, I was wrong. No big deal.

What I do want to do is get back into a new pair of regular fit jeans now that I've lost some weight. I currently wear relaxed fit, but have lost 25 lbs since I started biking to work a few months ago. I weighed 205 lbs in April. I'm down to 180 now.

[johnieheel]

Way to go sandalfan. It's your world and who cares what other people think. All down heel now bud.

[Guest]

I like your atittude johnieheels! thats exactly how I feel about it too! I could really care LESS about that other "5%" out there- I feel that since I do not KNOW them & vice versa, & since I DID NOT ask their opinion if they approve me wearing my boots or not, I do NOT need (nor want) their opinion anyway,not against free speech ofcourse, there IS such a thing as keeping that opinion to themselves, somthing I've found that a lot of people do not know how to do!

[JeffB]

SandalFan: Cool boots! Big thumbs up!

[roniheels]

SandalFan... Congratulations on your outing and your purchase. Those are some great high heeled boots. If you bought those at Payless, I'm going to my store to see if they have a pair like them in my size. Your responses to this first experience are what all of us felt and conveyed on our first time wearing high heels in public. Every time out is just as exciting, believe me. And you start thinking of other places you can go wearing high heels in public. I am so happy for you and your first experience. Congrats again.

[hhboots]

Great looking boots... Very nicely told story of your first outing and congrats on doing it. It sounds like you are well on your way. After nearly a year of doing street heeling, I am much more comfortable about it, but still have some hesitation taking that first step out of the car and still get quite a bit of adreneline surge every time I do it. There is nothing like it.

[Dawn HH]

That was sure a great first outing in your new boots. You just put them on without breaking them in and you may find that as you wear them they will feel and fit much better as you use them. You will also find that the more you streetheel the more that your feet will get used to you being in heels on all sorts of terrain and flooring and be more comfortable doing it. Congrats! Don't stop streetheeling now. Enjoy to the fullest. I concur with your views on taking care of your wife as I have been in that situation myself recently. Mickey says that I have to spend much time taking care of her and she is right and we are on our 40th anniversary now. My reply to her is to check out her wedding vows. We never know how we will be when we get older until it happens so we just make the best of it. Keep streetheeling and keep us all posted on your adventures. Cheers--- Dawn HH

[Henri]

I have the same shoes. I was at Payless thrying them on when the Store Manager walked by and said they had just come in and were fantatstic. At the time I only had one shoe on and she told me to try them both on and walk with them. I did. I loved them. I did not walk out with them. But last Thursday; I had an appointment for a dental cleaning. All of the office staff at the dental office are always in heels. YES, I wore them to the dentist. It did not take long for them to notice my heels and soon everyone was coming to reception to check on one thing or another and saying Hello. It was so obvious. When I got into the dental lab for the cleaning; the tech said " I have to ask" and I told her. I prefer to wear heels over flats. I am more comfortable in them. The only comments received were; "They look Great" and " I was wondering how they would look with my outfit." On Friday, I sent them an email asking when my next appointment and asked if they had gotten over the shock. The reply was the date of my next appoinmant and no one was shocked. They also said that I could stop by anytime in heels. It was a great experiance. Henri

[Dawn HH]

Henri:-) That's a great looking pair of heels. Are yours black patent? I'll bet you will take much better care of your teeth now that you know you can comfortably wear your heels there. Cheers--- Dawn HH

[Phoenix]

Great story. Also some fine looking boots

[SandalFan]

About an hour ago, I returned from another trip to the grocery store, to pick up a frozen pizza for dinner. Earlier today, I wore my biker boots to Kohl's, where I bought two new pairs of regular fit Levis. This is the first time I've worn regular fit since my early 30's, when metabolism slowed and I started gaining weight. I've worn relaxed fit for the last several years now. It feels great to be back in regular fit. They look a lot better with my new ankle boots, too.

The grocery store wasn't nearly as busy, so there were plenty of parking spaces near the door this time. Once again, I didn't hesitate for a second to get out of the car. I've already broken the ice with my first outing, and the anxiety I felt then is completely gone now. Nevertheless, my heart was racing by the time I got to the checkout with my dinner, just because it was so incredibly exciting to be out and about in heels for a change.

While shopping, I caught a few people doing double takes out of the corner of my eye as I walked by them. In the Express lane, a small line of people had formed behind me as I awaited my turn. Among them was an elderly gentleman right behind me, who managed to steal a few glances downward. When my turn finally came, I just casually moved forward and paid for my dinner, minding my own business like I always do. On the way to my car, I passed by another guy who also did a double-take. I just kept moving as if it were normal for me to wear heels - very casual, very confident. I made it back to my car without a single incident.

Again, no one said a single word. It was awesome!

You know what I find especially interesting? I don't know about any of you, but when I'm out in public, I'm constantly on the look-out for women wearing heels, just so I can admire them, and envy their freedom of expression. I've gone street-heeling three times now, and during all three trips, I haven't felt the least bit curious about what women are wearing, because I'm the one in heels. I don't know why, but the psychology behind that is fascinating to me. It feels really great to finally have the confidence to express myself that way.

Here's a pic of what I wore tonight. The shirt is a lace-up poet shirt I bought from International Male about 10 years ago. You can't see it very well, but I'm also wearing my hair down (I have waist-length hair).

[HappyFeat]

... Earlier today, I wore my biker boots to Kohl's, where I bought two new pairs of regular fit Levis. This is the first time I've worn regular fit since my early 30's, when metabolism slowed and I started gaining weight. I've worn relaxed fit for the last several years now. It feels great to be back in regular fit. They look a lot better with my new ankle boots, too.

I am assuming by your post that you have lost some weight. Congratulations, that is no small undertaking. I am currently working on dropping about 30 pounds myself. One of the things I notice as a result of wearing heels is being more fashion conscience, whether I am wearing heels or not. Great job i wearing the jeans you like and even better if you feel better wearing heels with them.

You have had a remarkable weekend!

[roniheels]

I have the same shoes. I was at Payless thrying them on when the Store Manager walked by and said they had just come in and were fantatstic. At the time I only had one shoe on and she told me to try them both on and walk with them. I did. I loved them. I did not walk out with them.

But last Thursday; I had an appointment for a dental cleaning. All of the office staff at the dental office are always in heels. YES, I wore them to the dentist. It did not take long for them to notice my heels and soon everyone was coming to reception to check on one thing or another and saying Hello. It was so obvious.

When I got into the dental lab for the cleaning; the tech said " I have to ask" and I told her. I prefer to wear heels over flats. I am more comfortable in them. The only comments received were; "They look Great" and " I was wondering how they would look with my outfit."

On Friday, I sent them an email asking when my next appointment and asked if they had gotten over the shock. The reply was the date of my next appoinmant and no one was shocked. They also said that I could stop by anytime in heels. It was a great experiance.

Henri

Henri...

I bought a pair like those in your picture on Thursday. I wore them all day, they were so comfortable. I had complements on them from some friends. This seems to be the high heel of the moment.

[SandalFan]

I am assuming by your post that you have lost some weight. Congratulations, that is no small undertaking.

Yup! Last April, I discovered that I weighed 205 lbs. The discovery prompted me to use Bush's "economic stimulus" package on a new bicycle - my first one in 17 years - and start biking to work. I lost 25 lbs in a month and have kept it off ever since. I'd like to lose another 30, but I seem to have leveled off.

One of the things I notice as a result of wearing heels is being more fashion conscience, whether I am wearing heels or not.

It's interesting, isn't it? I feel so much more confident street-heeling while looking nice than I imagine I would have if I hadn't cleaned up first before my first outing.

Great job i wearing the jeans you like and even better if you feel better wearing heels with them.

Thank you.

You have had a remarkable weekend!

Indeed!