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So today was the day for me to wear my boots outside my pants. I did a short 2 1/2 hour in public with my Nine West knee highs and these vegan leather pants as a test run. But today was a long one, 16 hours. I wore my JS Rollin knee high boots and vegan leather pants. First time wearing the JS boots and love them. Easy to walk in, easy to drive in and gorgeous!! Got lots of compliments on them, especially from women, but the most interesting comment came from a guy. "I wish I had the confidence to wear boots like that."

OUTING: Alright, so this is actually a comparison of two different outings on two different days. About a week ago I bought some shoes like the ones below in the image, similar style, but the colour is solid gray/brown, rather than the leopard print. I think it doesn't look too feminine, and I wanted to buy something that didn't look too feminine (like a stiletto heel). The heels on this shoe are very chunky, and the shoes look great, and are very comfortable. ~3.5" lift, can barely feel it when walking. I bought them for sort of "casual wear". I was so excited by the purchase I put them on, with dark blue jeans, and a sweater and went to a store. I was so nervous, felt my heart in my throat, and almost had a panic attack. Still went in. As I'm standing in one of the aisles, some old guy stops at the end of the aisle and just looks (90% sure at me), and looks and looks. After a few minutes I glance at him, and he walks away... The day following, I decided to try again. Similar outfit... But this time I was not at all nervous, very calm and comfortable. Went to 4-5 large stores in total over almost 2 hours. I even checked out some heels in 3 of the stores, which is my first ever time checking out heels while wearing heels. I could not have denied who I was interested in buying them for, if someone asked. I didn't find any shoes, although did buy the stuff I needed. I was very calm, very comfortable, and very happy afterwards. Halfway through the shopping trip, I even started leaving my comfort-item (backpack) in the car, which I've also never done. It was a lot of fun casually strolling around... Quite a few people around, I did notice a few people look, but got 0 comments. The sky didn't fall. Pushed myself out of my comfort zone a bit further...

As promised here are two pictures of what I wore last week in Toronto I chose the chunky lace up boots for walking up to the exhibition place,from the Westin Harbour. 45 minutes the other outfit was for the travel. 2 days ago I was in Paris wearing these same chunky front lace up boots and as I was waiting in a fedex agency I had the pleasure to hear a young girl tell me’ I love your boots!’ So: one positive comment,no negative one. Pierre

You Rock Those Sandals !!! OK, this is getting weird... Last Monday I got a very positive compliment about my heels from a guy at McDonalds - explained above. Today I was at Home Depot at the self check out wearing the same heeled sandals. One of the female clerks on duty, she appeared to be in her late 30's or early 40's came up to me and said, "You Rock Those Sandals!" I was in the middle of my transaction and did not exactly hear what she said, so I looked at her, smiled and said, "Are you talking about my shoes?" She grabbed my arm and said, "Yes, those sandals rock." I told that the shoes are one of my fav pair that I wear a lot. She said they looked great on me, she liked the "retro" toe loop look and wanted to know where I got them. She said they look fabulous, and she is always looking for nice looking sandals like mine. She asked if I get many stares or looks, I told her occasionally but no big deal. I said that I was maybe the only guy in Orange County who wears high heels, she laughed and said "probably." I asked her if she thought I looked unusual wearing a pair of heels, she smiled and said that while it's not usual to see a guy in high heels, I looked great in them and keep doing what I am doing. We made some additional small talk, she again said that she wanted a pair and continued the compliments. Prior to this week, I have not had anyone comment on my heels in several years. Maybe something is in the water?? The experience was very positive and uplifting. Had to share here... Wearing high heels is fun... Take care all..... sf

Stiletto Mania I have just purchased 4 new heels in the last month and the last three have been stilettos! Before that I had just one pair from Victoria’s Secret. Today I picked up two pairs that I had bought on-line, so I thought I would try them each on and do a photo shot with my faux leather Express pants. Photos are in a new album. Forget Black Friday This is Stiletto Mania! Here’s my new heels: Jessica Simpson RACHIE PLATFORM BOOTIE COLOR: Black Add refinement to your ensemble with the Rachie bootie from Jessica Simpson. The chunky platform and towering heel will boost the look of your favorite LBD. Product Details 4½" covered stiletto heel, 1" platform -- Faux suede upper - Inside zipper closure - Almond toe - Synthetic lining - Lighlty padded footbed Approx. 3½" shaft height - Approx. 12½" leg opening - Synthetic sole - Imported I got these in Size 10, slightly tight above the arch, but they should stretch out just enough. I really feel sexy in these. Jessica Simpson ROLLIN PLATFORM KNEE HIGH BOOTS COLOR: Porcini Product Details Jessica Simpson elevates your fashion aptitude with these Rollin dress boots that pair with a skinny mini or flowing midi skirt. PRODUCT DETAILS 4½" stiletto heel; 1" platform - Shaft height: 16½"; Circumference: 14"; measured on a size 6 - Almond-toe dress boots with zipper closure Covered heel and platform - Suede upper; manmade lining; manmade sole - Imported I got these in a size 11. I give these a 5 star rating. Been looking for a knee high boot with a full zipper for some time and when I saw these and I had a very special coupon from Macy’s I jump on them. So glad I did, these are sold out now. . I have had them on for the last 3 hours aand love them. Since I now have 4 pairs of knee high or almost knee high boots and have broken the ‘tight pants (leggings) with knee highs at work’ bubble, I plan on wearing these with those (faux) leather next week…maybe with my Sherpa. Plan to get a lot of use out of them. Steve Madden LURE Black Suede Mule Stilettos. Distinguished by a sky-high heel and dramatic arch, LURE tops the list of this season’s sexiest slides. Suede surfaces offer soft texture and a rich matte finish. PRODUCT DETAILS 4.75 inch heel height - .5 inch platform - Suede upper material - Man-made lining - Man-made sole By far these are the tallest of the bunch but fit great. Since winter is coming up, I don’t plan on wear these until next summer. These are also already sold out in black. Glad I decided to get them. Shorter steps are also required in these.

A short update--my "special" project at work is not yet finished, but some of it has been postponed. I am glad to be home at a normal hour these days, but on the other hand, I wish they would hurry up and get it over with. It is somewhat frustrating to tell the family, "I won't be available to do much of anything but eat and sleep on such-and-such days," only to discover I'll have to make that sacrifice at a later, unspecified date. The overtime money is certainly appreciated this close to the holidays. I haven't bought any new shoes for nearly six months, so I'm trying to make sure I'm wearing the more neglected members of my collection in addition to my favorites. I have had these Bakers Reissa oxfords for several years, but have never worn them in public. I have taken them for a couple half mile spins around the neighborhood early in the morning/late at night, but the fact is, I can't walk in them properly. There's basically a 5 inch difference between heel and toe, and my graceful limit is about 4 1/2". I can walk in them functionally, but it's not pretty to look at, and I can't go around looking like that. So I'm trying to expand the top of my height range, and I've started wearing them around the house, despite the fact that I absolutely hate wearing fully enclosed shoes at home. OK, I hate wearing fully enclosed shoes anywhere, but especially in my own house. Nevertheless, if I'm going to keep these shoes, I'll need to learn to walk in them, and that's not ever going to happen if I don't wear them. The other problem with these shoes is that they have a very short, rounded toe. I'm not a big fan a-them witch toed shoes, but I wish these shoes had a slightly longer, more pointy toes. The reason is that at this height/steepness, there is not much horizontal real estate being taken up, and you have to wear the slimmest, skinniest pants with them. Otherwise, with any flare or fullness at all to your pants, it looks like you have no feet, or that your toes have been chopped off. As an aside, I have bought some new leggings. I have yet to try wearing leggings out by themselves, but I use them both for my yoga practice in the winter, and for long underwear underneath basically everything all winter long. I admit to being cold-blooded, and that extra layer on my legs makes a huge difference to my comfort. My trusty three pairs of Hanes leggings are all looking raggedy and terrible, so I ordered two new pairs in a cropped length. I chose the cropped length because I have very short legs, and I was somewhat frustrated by the leggings sticking out the bottom of my skinny jeans when wearing no socks, an unattractive look in my estimation. So I took a chance on these Jockey cotton cropped leggings, size small. It was a good gamble. They fit perfectly. I wish they were a little tighter around the ankles, but I'm not going to fuss about it. I think they are actually supposed to hit you mid-calf, but as you can see, they hit me a little lower, which is exactly what I wanted. I can now wear clogs with skinny jeans and wear these underneath, and nobody is the wiser. I can still use the three old pairs for work, because who cares? I have to go to wool longjohns if it gets really, really cold. That's when fashion goes completely out the window, when I want to come home with all the fingers and toes that I had in the first place.

"I can do that" and "Just Do It" are two phrase to use. Years ago there were certain things I wish I had the confidence to do. I am finally getting the confidence to do many of these and I am much happier because of it. Last year I was a "want to expose my knee highs" type of person, this fall I got the confidence to break that self imposed glass ceiling.

I bought these at a resale shop a month or so ago for $20. Guess brand, no style name noted in the shoe. It appeared that they had never been worn. They have a heel of just a smidge over 4". For a stiletto, they are pretty darn comfortable, though I'm having my usual issue of walking out of the left shoe. I did wear them out shopping one evening, which is not like me as I tend to stick to less obvious heels when I am in public. It was a thrill for me, and I just loved the way the chrome ornament caught the light when I walked in them.

I'll leave these here.

Before I talk about my recent heeling endeavors, I wanted to take a minute to discuss a topic that has been talked about before, but until recently, I wasn't quite sure why I felt the way I did. The topic is complimenting women who I think wear cute heels/boots. For some reason, I have always felt that paying a compliment was in someway awkward, and I never knew why. I always worried that the girl might find it creepy or strange. Thoughts of "Why would a guy notice my shoes? Is he gay?" "Weirdo" "Creepy" etc. would always swirl in my head to the point where I freaked out just to pay a compliment. But over these past few weeks, I've realized that it's the fear of exposing my own heeling that has made the scenario awkward. Let me expand: Over these past few weeks I have been more courageous in wearing heels other than my Converse wedges at work. 1. I started with wearing my Sorel wedge ankle boots into the office, only to change them after getting in. 2. From there, I progressed into wearing them after my Friday morning workout when I would leave the office for a Starbucks and then return. 3. Then I started keeping them on when I would go to the cafeteria at the office to get my coffee, potentially exposing them to more people. 4. From there, I started wearing the Naturalizer boots that I bought to match my wife's boots into work on Friday mornings. 5. Then I added them to my Starbucks run. 6. Now I keep my Sorel wedges on most of the morning, including my morning coffee chat with a coworker who I'll mention more about later. In this span of 3-4 weeks, I have discovered that my comfort level for complimenting my coworkers has gone up. I can only assume that the increase in comfort has gone up due to the increase in comfort with wearing my heels. With that being said, I have a coworker who I usually chat with in the morning when I get my coffee from the cafeteria, and she her tea. She is aware of my heeling and indulges me in my discussion of cute footwear that I wish I had, etc. Well, it turns out that we are the same shoe size! Over this past weekend, she had sent me some pictures of some heels that she owns, saying I could borrow them anytime I wished. In return, I sent some pictures and told her likewise. One pair that she had which are super cute happen to be a pair of extremely comfortable Dr. Scholl's booties. She really liked a pair of Kelly & Katie heels that I own that I unfortunately would probably never wear. So today we each brought our respective pairs into work, each wore a shoe, and then proceeded to take a couple of pictures. I think they turned out really good! As we 'swapped' each other's shoes for a brief moment, I actually told her she could keep the shoes as an early birthday gift since I am unlikely to wear them. She was ecstatic and very grateful. It was a good feeling to know that someone else would be enjoying the shoes! The instagram pictures are posted below.

@hiddenheels its always nerve wracking when you expand your comfort zone. Especially those first few steps, we all experience it. But it is also very satisfying when you have expanded it. Good job.

Haven't been to this mall in ages & noticed they had a SHOE SHOW store now. Went in & found they had some larger sizes available. Ended up buying a pair of HOT TOMATO booties & my 1st pair of over the calf boots by ITS OK! Had a nice talk with the sales girl. She said the 12' & 13's don't last long. Other than the mall kiosk urchins harassing me it was a good trip. Sorry didnt notice the booties pic was blurry... TY! Gave me a chance to rest easy, if only for a little while. Gonna drive back down tomorrow afternoon to give her the candy & say hello, then drive back...

So sorry for all that are dealing with health and other issues of their loved ones. It is not easy. Hope you can find some comfort. We often forget that the members here are just like the rest of the world and are dealing with life's ups and downs and not just the issues related to our footwear choices. Best wishes.

You look amazingly powerful and masculiine indeed, great look buddy...Sure wish I was in Toronto last week! How are those boots to walk in?

My standard response to why I am wearing heels is "because I want to..." It's not a problem for me, so I don't see why it would be a problem for anyone else. Thats my attitude about my heels wearing anyway. In reality it just hasn't come up much at all. The comments / reactions have been overwhelmingly positive so far...worst I have had to deal with has been a couple of "look at his shoes", always from so old guy I don't care to talk with anyway... Nothing....the only comment i have ever gotten in 2 years was from some stranger passing me by in a hallway that said "ohhh, your nails!" but he had a friendly smile on his face & i took it as a playful, pleasant response. The guys in my office have not said a word one about my nails, at least not in my presents. Now women, well they are all over it! Not going to be able to do any heeling for a while. My mom has been in poor health & she has taken a turn for the worst. I need to spend the weekends taking the place of my sister, who has been keeping mom company in the hospital, so she is not alone. It's been a rough year emotionally, so my return to wearing heels has been part of my effort to find joy where I can. It's been hard to watch the last of my families elders fade away like this. I don't want to face the holidays at this point, but I have to carry on the best I can...

@kneehighs when we first started dating I did let her know I liked women's shoes and that I had an interest in crossdressing. She had absolutely no animosity towards it. She encouraged it. She helped me do my first outing in public. She has purchased me insane boots and heels. She still does.

Actually in the Spring area north of Houston. Thank you for your kind words! Thank you! The Pneumonia is mostly under control but they discovered the 2nd infection they were hunting is one of those damn super bacteria. They have her on the strongest anti-biotic possible. Its in her intestines & she had it before getting hospitalized, so in a bizarre way the Pneumonia probably saved her life, cause the bacteria would have killed her within days. We had to put on scrubs & gloves to be with her & washed with some nasty soap afterwards. After tonight's visit I plan on returning this weekend, now that she is somewhat stable. I brought some Jessica Simpson heels I want to try to break in with me thinking I might stop on the way home to eat but was too weary, so maybe later...gonna keep some heels in my car to take advantage of any opportunity that may arise...

chesterx, Welcome to our forum and for sharing your outings as well as recent news on your mother's recovery. I'm guessing you are in the DFW area but that's just a guess. My wife and I were there in July for an uncle's (by marriage) funeral. I had finally gotten to know the guy in October of 2018 only to see him succumb to some really painful and progressive disease. But I did succeed in knowing him. I'm glad your Mom pulled through. Pneumonia takes more people than many realise. Again thanks for joining our group and sharing your photos. You're in the right place friend!! HinH

Hi guys! Good news as the doctors were able to get her pneumonia under control. They were not expecting her to recover at all, but she has, and it has bought her some extra time. She is still in ICU but she can breath on her own now & get some restful sleep. Now I can too! She asked me to bring her some chocolates so I stopped by the local mall after work. Wasn't gonna let this opportunity go to waste. Slipped on my Chelsea Moreland nude pumps & had some fun. They are a little tight but I only paid $10 for them.

Mr. X 3:16 says Well done!

Jaunt #526, 11/16/2019: BBRRRRR!! While the calendar says mid November, it felt more like January or February as it was plenty darn chilly outside for this latest outing, all the more reason to spend the time indoors, and that meant going to King of Prussia and the mall. And because I was going to be inside, I didn’t have to bundle up like an Eskimo, still, I dressed for the occasion in my black faux leather jacket over a black turtleneck, a black and white print midiskirt from JCPenney, black tights, the Payless “Martinez” ankle boots in black and a black satchel bag. Here’s a new number for your perusal: this was my 200th outing in boots since I began this thread eleven years ago, easily the leader in the footwear clubhouse at nearly 40 percent of the overall total. Funny thing, when I first started out, I had no idea I’d be so partial to boots, whether they be ankle high, knee high or thigh high, and, of late, I’ve especially enjoyed wearing ankle boots which are cute and work well with skirts, dresses and leggings. But, I digress. At this time of year, the mall is both full of people and highly festive because of the holiday as the place had been decorated for Christmas since after Halloween. After a stop at the comic book shop, then Modell’s Sporting Goods for a package of sweat socks, it was off to the food court which was packed at a hair after twelve, I went to a brand new eatery there, Popeye’s as I was curious about their chicken breast sandwich which had gotten boatloads of press when it first came out a couple of months ago and quickly sold out, all things considered, it was pretty good, I’d put it ahead of offerings from the likes of Wendy’s, McDonalds, Chick-Fil-A, Arby’s and Burger King, not bad, not bad at all. I can understand what all the fuss was about, I’ll certainly have to have that again on a future trip. After lunch, a leisurely walk through the crowded mall took me to Old Navy where I bought a sharp, black wool peacoat to wear in the winter months to come, and a cute slipdress for spring and summer. As I became more and more involved in freestyling, I became driven with making sure I wear not so much as one stitch of men’s clothing on my outings, from outerwear to underwear, and that meant making sure I had a women’s coat for cold days, and this new purchase should fill the prescription quite nicely. At Primark, I kinda sorta broke a promise. I know I said in past posts that I wouldn’t buy any more skirts as I was sloooooowly transitioning to wearing dresses full time on my outings, but I saw a couple of cute numbers there, one plaid, the other a cream cable knit that I couldn’t resist. However, I balanced that out by adding a cream cable knit sweater dress which should work nicely on cold days that are on the way. A pretty good haul if a do say so myself, and I can’t wait to show off my new purchases. More to come....

Just black Patent laceless Wearable Cap Toe Oxfords. Never met a girl, including the GS girl, who didn't compliment them. That's my default, but I didn't even wear that this evening. No follow up date with GS girl. I forgot to add she started to take off her Manolos to let me wear them. Unfortunately, I'm just not that attracted to her. I think the context that lead up to that was me asking what size she wore, her answering "39", me saying "OMG, that's just about my size! (it's a playful comment)...." I probably won't follow up with her. I did meet some other blonde that same night who I'm direct messaging on IG to see if she'll hang.

It just happened that way. What can I say, I like a wide variety of heels. Macy's had a special flash sale on boots, 40% off + free shipping, so I thought I would give the JS Rollin a try. Then a few days later Steve Madden changed their rewards system and gave me some % off, + $30 off, and free shipping. I saw they had this tall mule, it just so happen to be a stiletto. Then one day I had two hours to kill so I went to see what was at DSW (big mistake). The JS Rachie captivated me as I passed by them.

Not like you with the stilettos Cali! But looking good.

Just got back home after spending all day with her at the hospital. She is stable in the ICU. Doesn't look like she will leave the hospital. The worst part is she is so scared & there is just nothing I can do to comfort her. I feel so helpless & emotionally exhausted....

I would wear my Nine West knee high boots outside my pants.

Sorry to hear... Hope she recovers. My mother in law will be moving in with us next month, for good it seems. Financially she just can't manage on her own anymore. And we can't afford her rent anymore either... So wondering what impact that will have on my home heeling too.... I feel for you buddy. Chin up, as it seems you have anyway and try take care of yourself too.

They should get complimented. Those are great boots Pierre.

Another word of caution here, women hate it when a man wears it better than they can.

They don't make them in leather any more. At least the boots. I still have an old pair, I should on what they look like these days. I love the matt leather look. Never been a patent guy myself. And they really were the most comfortable 5.5" heeled shoes you could and probably still can find.

Heck, I forgot about all those outlet stores. Don't get up around Conroe much these days. Thanks for the heads up, always open to new shopping opportunities.

Happy to hear the update @chesterx, may she continue to recover. and happy about your new acquisitions too - well done!

I don't really hate these shoes, but I also don't love them. I assume you wear U.S. Women's size 12 by your comment? Unfortunately, these are U.S. Women's size 9. If they fit you, I would just give them to you, because I know you love oxfords of all stripes.

A coworker of mine that lives in Minneapolis calls this "responsible fashion".

Your adventures never cease to amaze me kneehighs.

Nice shoes! You don't often see oxfords with that high of a heel.

I like the monochromatic undertone of black. You look good and your spirit looks vibrant. Well done.

mlroseplant, I understand the cold stuff and dressing for it. I just returned from our land in far northern Wisconsin where it dropped to -10F (-23C) on Monday. That's an unheard-of low temperature so early in the winter season. My ponds were completely frozen and I was able to practice skating on them which again if very unusual so early in the season. I did like the shot of the Bakers oxford heels. HinH

I hear ya buddy, being a care giver is emotionally and physically exhausting for sure. My Mom is scared also, all you can do is be there, there aren't many words that can comfort. My Mom is such a fighter, have learned never to "count her out", somehow she bounces back. I just don't want her to linger, hoping we can have a nice steak dinner, tell stories, have some laughs, and she will pass in her sleep....Wish it was that easy.... Please take good care of yourself....

Waiting for a medical test at the hospital. Wore my Sorel Lexie wedges with grey and white socks over Lululemon Speed tight leggings and a Lululemon black 1/4 zip with my new North Face 550 vest. Many looks and a couple of nice comments

what brand and model are those 2 pair of booties ? Prutske255

Thank you so much for these comments Those boots are amazingly easy to walk in. 2 hours shopping,sidewalk walking without any trouble or pain. And the heel is 15 cm. Minus 2 cm sole .So 13 cm real height. I love them. And I now even forget I am wearing them. I have ordered some more to FLS shoes and am waiting for the delivery Pierre

That's great. Not being able to give a direct response right away prevents many from public wearing. I'm now the third oldest in one family tree with my mother and her brother the only ones above me. Visiting her is one of the few times a year I have clear nails.

Congratulations on your recent purchases! They all look great, and I'm sure you'll get a lot of use out of them. I really like the thinner heels, at least for myself. In my fantasy land, I would wear nothing but super thin stiletto heels. In the real world, these slightly thicker, higher-than-almost everybody-else, but lower-than-fetish heel height is so practical and comfortable.

Any boot guys in DC interested in meeting up for coffee/snack this Sunday, 11/17? I will be staying at the Marriott at Wardman Place, get in around 3PM...Don

Ordered a couple of different boots in English red a beautiful colour. Wiehes by my wife.

I still have the same pair in matte leather. The material has been coming apart for years and I've found the patent leather holds much better.

Wow @chesterx, that quite a story, a lot of heels! Where do you keep them all? And have you worn them all yet? Luckily... I am pressed for cash... Otherwise I'd buy more too!!

I recently wore this exact outfit to the eye doctor, a diminutive but stylish woman, who couldn't be over 5 feet in height. She said, "Oh you shouldn't wear heels around me. I tell my 5'10" husband to always wear flats!" The comment made me wonder what her husband's non-flats were exactly. These are inexpensive boots from Forever 21., but fun for a lark.

I feel for ya. Not too far off here too.