SandalFan

I wanted a pair of the ankle-straps that Gwyneth Paltrow wore in Iron Man, until I found out they were $600. I will never be caught dead in public with any of my pumps or sandals, and I refuse to pay more than $50 for a pair of shoes I have intention of wearing outside my house.

Wow... for the first time since registering 3 years ago, I can actually contribute to a thread like this... nice... With the exception of a few poet shirts, my entire wardrobe is T-Shirts and jeans - all black. My choice of day-to-day footwear is pair of black leather biker boots I've owned since I was 20 (damn those boots are durable!). As of last weekend, my choice of off-work footwear is a pair of black, Victorian-style lace-up ankle boots with a 1/2" platform and 4" stiletto heel, that I bought last Saturday.

Grats! Well done!

Great looking boot. I just might go and take a look myself this week but I prefer a taller shaft (knee high) with a 5" heel. More important is... Do your boots feel like they give you good ankle support?

Thanks. Yeah, they have excellent ankle support. Very soft, very flexible.

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!

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).

I went street-heeling for the first time, yesterday afternoon, and opted for the same over-the-calf tube socks I wear with my biker boots. The more comfortable my feet feel, the happier I am, and socks with 4" ankle boots are very comfy!

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.

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

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!

Why do I find it rather peculiar that most everyone who's replied to this thread so far is actually either embarrassed by the fact that they own any mens shoes, or refuse to own any at all? I'm the very proud owner of a pair of men's black work boots, and a pair of men's black Biker boots, both of which have lug soles. They're extremely comfortable, and are a very welcome relief to my feet when I go out after wearing my heels for long periods in the privacy of my home.

I wanted a unique look, foxy and flirty, that was all mine. The problem was, that I didn't know how to do it.

Dude... seriously?

If you have a significant other, you should consult with them to find out what's considered "foxy and flirty", because what you just described isn't. I don't like the image I have in my head, I don't even want to see a picture of you in that outfit. For that matter, I wouldn't want to see a woman in that outfit.

I think the two girls who complimented you were just trying to be nice.

Hence my feeling that block heels are better than stiletto heels for men as the former is sturdy whereas the latter is dainty.

That's one reason why I won't wear heels in public. I detest block heels. I won't even look at womens shoes if they have anything thicker than a stiletto heel. In other words, the more feminine the shoe, the better to add to my collection. Unfortunately, most of the guys who go out in heels and post about their experiences wear block heels when in public. Those posts do not inspire me.

You really want to inspire me? Go out heeling in a pair of 4" stilettos. They can be boots, just as long as they're no shorter than 4" and are stiletto heels. I would love to be inspired to try these on in public:

http://pleaserusa.com/pic/Seduce-1020.jpg

I adore ankle boots, and would love to have the confidence to wear those in public.

But to be seen in obvious heels here in the conservative Midwest USA is another thing entirely.

You make an interesting point. Most of the heeling journals I read on this board are authored by people who live in areas of the world that don't ordinarily think twice about seeing a guy in heels. People may find themselves doing a double-take at such sights, but I've yet to read of a single instance of anyone being assaulted for wearing women's shoes in public. The only real concern they have to overcome is anxiety.

I, however, live on the edge of The Bible Belt. As inspiring as the journals I read here are, if I started wearing my heels out and about - even with jeans - the risk of attracting unwanted attention is a good deal higher.

There is a certain mystique about the look of pants over heels... is probably more interesting than the heels in full view.

Pants over boots = sensible

Pants over sandals and pumps = BAD! Very, very BAD!

I hate it when women do that! What's the point in wearing a sexy pair of pumps or sandals if you're not going to flaunt them with a skirt or dress? That's another reason why I don't wear heels in public. I don't do skirts or dresses either, and I don't own any boots (hence my nickname).

Nice choice. Will you be wearing them out?

Thanks. No, I only wear my heels inside.

This evening, I decided to stop by Payless Shoe Source on my way home from work, to see what new styles they've got. Shortly after I began browsing the women's section, the clerk came around and asked me if I needed help finding anything. I politely declined her offer, and then she left.

A few minutes later, I decided to see what new hiking boots they were carrying for men. I found a pair I wanted, but decided to buy them later. I then went around to the next isle, to ask the clerk if they carry over-the-calf tube socks. Having only just seen me browsing the women's section, she picked a pair of disposable nylons out of a fitting box and asked if they were what I meant. I clarified my request by telling her that I was looking for men's tube socks, all the while mentally chuckling to myself.

I seldom browse women's shoes in person - once, maybe twice a year. I already know what size I wear, and if something I order online doesn't fit, I simply return it and order another size. My encounter with the clerk was only mildly awkward, but I did find it both interesting and encouraging that she appeared to think nothing of the possibility that I might want to try on a pair of women's shoes. To her, I was nothing more than a potential sale.

If I could go back in time, I'd travel back to the 1940's, when skirts and dresses were the norm and women always looked like they were dressed in their best - they were beautiful, classy, and very demure. Of particular interest to me are the heels they wore back then, especially the ankle-straps. Not too high, and not too low, yet nearly always on a stiletto heel and quite sexy.

Last night, my wife showed me a commercial for a new line of shoes from Payless. One of the featured styles this season is an American Eagle Karoline Platform Ankle Strap Sandal, the design for which was inspired by 1940's fashion. As luck would have it, they're also on sale for just $9.99, discounted from $22. Suffice it to say, I lept at the opportunity to own a pair, and placed my order post haste. I'm expecting delivery in about a week. I can't wait!

http://tinyurl.com/yrf34r

I don't know what it, what caused it, nor can I fully explain it, but just like back in the spring, I've lost my interest in wearing heels----again.

You may be experiencing a desire to be physically comfortable instead of trying to be a trend setter. It's why I never wear my heels in public. Getting over the fear of public rejection is one thing. Having to maintain the posture required stay balanced in a pair of heels all day in the first place, I imagine, would be a whole other beast. Frankly, I'd rather not put that much stress on my feet and ankles. I love wearing my stilettos while at home, but I prefer the comfort of my hiking boots when out and about any day of the week, especially on rare occasions when I find myself in a mad dash to get somewhere fast.

One word describes those shoes: Blech. I detest platforms.

Height, definitely. They can look sexy as hell, style-wise, but if they're on anything less than a 4" stiletto, no, thanks.

No comment on the dads in heels, but Hanna makes reason #3,458 why I'm glad I'm 36 and child-free. E-gads...

Myself, I just want to be a guy in heels with my blue jeans and t-shirt or (guy clothes).

Ditto that, though I have worn pantyhose with my shoes many times, to enhance the overall appearance.

I've seen myself in a dress. It's not a pretty sight.

lol

Nice pics on the last 2 posts. Do you guys both wear them out?

You have no idea how much I'd love to. Alas, my heels are strictly for around the house.

Besides the high heels, I find myself buying and wearing women's sneakers, clogs, work boots and semi dress shoes. Just interested to know if other members are so inclined.

Nope. Heels only for me, thank you. Otherwise, what's the point? If I want to wear anything flat, I have my hiking boots for that.