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The Happy Feats of HappyFeat


HappyFeat

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HappyFeat, If you're going to visit Johnie and Ruthie, send me a private message telling me when and if I can, I would love to join you. We should all get together again. Too bad the October heel meet didn't work out this year. Steve

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Well, HF, I know I really shouldn't be posting my adventures on your thread, but I have to say that it's all your fault....lol. I went out Christmas shopping in my 3" heel boots last night. I was fun to walk around a couple different department stores. Once again, I don't know if anyone noticed, as I just went about my business. Unfortunately, I am finding that I'm going to have to look for some alternate boot or shoes to wear out, as these boots are just not quite wide enough. Tow are is fine (that's where I normally have a problem), but the right boot is a bit too narrow through the ball of the foot, and I am getting pain across the top of my foot. Anyway, walking around Sears takes on a whole new meaning for me now!

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Happyfeat:-) Being a boot person myself, pic #3 did it for me as well as for you. Certainly a good look for you and congrats on you being able to lose a few pounds. It sure does make a big difference. Cheers--- Dawn HH

High Heeled Boots Forever!

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Well, HF, I know I really shouldn't be posting my adventures on your thread, but I have to say that it's all your fault....lol.

RonC, if it is indeed my fault, I am happy to take the blame! Post anywhere you want and congratulations on getting out my friend!

Last week was pretty remarkable for me. I got out all five days, only breaking on Saturday because of a pretty big snowfall. Since I was finishing my Christmas business (and doing a bit of shopping for myself) it was a fantastic opportunity to get dressed and get out.

Tuesday December 15 - My plan was to get a haircut (which I desperately needed) and hit the mall. However, due to a couple of home maintenance issues, I didn't make it out until much later than I had planned, which pretty much scrubbed my haircut plans. I wore a black lambswool Docker's pullover, gray Lane Bryant "Lafayette" dress trousers (which have a nice high waist) and black suede/leather Bass "Alansis" booties. Though I thought the outfit went together OK, it wasn't nearly as flashy as I had worn recently.

Before heading to the mall, I stopped at my bank to deposit the money that would soon disappear. I had a very nice chat with the tellers, who are becoming increasingly flirty and friendly. I know it is obvious to them that I wear heels, but they never mention it, so we never discuss it. Next, at the mall, I went to The Limited, which is rapidly becoming my favorite place to buy clothes. This store is the only one in the immediate area, and I only visit it about once every six weeks, but I think they are getting to know me. They had a 40% sale on all of their denim, which still put the jeans in the $40 range - I know a great price for decent jeans, but I am a pure clearance guy. I found a pair of skinny jeans (not on clearance) and the clerk working took me to a dressing room without asking. She was telling me how comfortable they are and how much I will love them. When I tried them they were perfect, and clearance be damned, I had to have them. I took them out and she told me that they had a special if I spent $50, I would get $25 off my next visit, so I dug through the clearance rack, found a pair of fun crop pants, which didn't fit terribly well, but for $12, I thought I would give them a shot. All of the clerks told me to "have a nice evening" and to "come back" on my way out. A very nice shopping experience.

Next, I went to Aldo, which was packed. The small store must have had 6 people working. One girl greeted me and asked if I was looking for a Christmas gift. I said no, I was looking for something for myself today. She said that was really great and that women's shoes are so much nicer than guy's shoes anyway, so if I needed anything just ask for her. I did ask for a couple pair of boots, but they were out of my size. I hit Banana Republic, the Gap, JCrew looking for Christmas gifts. AT JCrew, I tried a pair of "Toothpick" jeans, but needed just once size larger. My final stop was getting some tools at Home Depot for gifts. One warning - the floors are a bit slick in Home Depot, so be careful if wearing thin heels in the store.

Wednesday December 16 - Again I still needed a hair cut. With my hair, thinning and turning gray all too fast, I wasn't quite sure what I wanted. I was either going to get a buzz cut or color it. I could no longer stand being gray AND bald, it was going to be one or the other. I friend told me about a hair color treatment for me at Super Cuts that I should try, so I thought what the hell. I tend to be a bit of a snob about hair places, but I thought I would give it one last shot.

I wore a red Ralph Lauren sweater, by new skinny jeans from the limited and my black Steve Madden "Stretch Out" boots, over the jeans of course. Other than getting the wide eye look of shock from the women working in the salon, there was no mention about my attire but everybody was very friendly. I got my cut and color treatment from a very nice redhead in her early 30's. We chatted the whole time, she smiled when we made eye contact, and gave me an incredible scalp massage. Sometimes I wonder if wearing heels isn't something that actually get me better service in some cases. My hair looked great! A nice haircut (and shaking a bit of the dull gray) gave me new found confidence.

Afterward, I went to Starbucks for a Hot Chocolate where I received practically no attention and to a discount book store where I continued my Christmas shopping. Again little to no attention. But I was just feeling great, with new hair, in my new jeans, and my great boots. Another fun outing all the way around.

Thursday December 17 - I decided to try the new Limited black/white crop pants. They don't really fit the way I like, a bit low in the waist and too baggy in the bum, but thought they would be cute with my Enzio Angiolini "King" lace-up boots. A added a black Claiborne sweater and headed out for me shopping. I went to Marshalls, where I toyed with the idea of getting a pair of $40 Nine West boots, but decided to wait until after the holidays and return to the outlet, where I am guessing they will be marking down their inventory. I bought several pair of socks, etc. for some of the women in my life and browesed their clearance racks. The problem with places like Marshall's and TJMaxx, is that most of the stuff they sell is rather "ordinary."

Next I popped into Starbucks, which was quite crowded. I got a few looks, but nothing too terribly obvious, except one guy who was trying to take a picture with his telephone. I really hate when people do that. If he would ask, I would actually pose for him, but the sneaking around is just obnoxious. Anyway, I made it difficult for him by moving, then stopping, then moving again. The shutter speeds are so slow in the low light, that action stuff is really hard to turn out.

Next, I went to a consignment store that just opened. There were three women working, all very well dressed, all had deep olive complexions, and all had thick New York accents. The store was a bit over priced but I did find a great pair of black Michael Kors pumps in all leather. I also bought a black denim Ann Taylor skirt. I talked to one woman working about the shoes she was wearing, great black pointy toe d'Orsays with a cream colored bow. SHe said that she hadn't decided to get them, because she really isn't a "bow girl." I said that they were nice and the bow wasn't even that girly. She asked what size I wore and said that they would be too small for me.

I headed to the Ross Park Mall on the north side of town next. I needed to hit the Body Shop for gifts for my mom. A walk through the mall got me a lot of attention, mainly from guys who were a bit shocked. At the Body Shop, the clerk was not impressed but friendly. I got what I needed and headed on. I stopped at GNC, where I couldn't find what I was looking for. I asked they one clerk on duty - a woman in her late 20's - and she said they didn't carry it in their store. She noticed my outfit, was quite friendly. When I got to the entry, I looked back and she was watching me, smiling in a very friendly way. Finally, I went into the Nine West store, where there were a few pair I wanted to see, but the store was so overrun, that I didn't even bother. Again, a trip for after the holidays.

Friday December 18 - Since I had done pants all week, I decided that I would wear the skirt I bought at the consignment store the day before. It is black denim, straight, and slightly above the knee. I matched it with a black turtleneck, a pale yellow Nautica sweater, black opaque tights and the Steve Madden "Stretch Out" boots. I went to the outlets initially. At Nine West, i tried a few pair of shoes and even made some recommendations to an African-American woman in her 40's about comfortable shoes in a size 11. She actually bought two pair. The cool thing about this interaction is she seemed to not care that I was a guy, that I was wearing heels at the time or that I owned the pairs I recommended. It was just very natural and fun.

I went onto Lane Bryant, Jones New York, and Casper, where I tried on a black and white houndstooth dress. The manager, I had have chatted with before, even came to the dressing room and zipped me up. She told me that it looked better on me that anybody who had tried it on yet. It was nice, bit a bit frumpy for my taste, but it was fun trying it on. I stopped by the makeup store where the manager offered to color match me. She applied a little foundation, and even helped me pick out a couple of lipsticks. She took my e-mail and said that when they have a sale, she will let me know and I can come back for the whole treatment. Though she picked them for me, the lipsticks will make great gifts for a couple of women I know. Can't all be about me...

Finally, I stopped by the consignment store where I have sold some stuff. It was a bit crowded and there wasn't much I liked. However, I ran into the woman who owned the store I was in the day before! Quite ironic I thought. She was very friendly and we chatted for the better part of an hour. She had found a pair of Carlos Santana slingblacks and I told them I thought they were wonderful. She said that when they get any 11 shoes in she will hold them for me to look at. After she left, I chatted with another woman who invited me to her New Years eve party. I gave her my e-mail, but told her that I already had plans. Pretty exciting day. After giving the owner a hug, wishing her happy holidays, I headed home to hide from the coming snow storm.

This has been a pretty great week. Though I will get out a couple more times before the end of the year, this is a great cap on a great year of heeling for me!

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Style is built from the ground up!

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Greetings Tom :-) Nice outings and it looks like you enjoyed them to the fullest (This time my favorite is pic # 2) and you got a lot of nice interactions with the salesgirls and customers. (Wondering if it is because you were wearing heels) The skirt outfit is also nice.

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Yo, HF! Bravo to you on your latest exploits! And your outfits were great as usual. Of course, my favorite was pic #4! The sweater/skirt/tights/boots combo was terrific! And your outing in said outfit sounded like a really good time! Two thumbs up!

I don't want to LOOK like a woman, I just want to DRESS like a woman!

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I like the skinny jeans and black Steve Madden "Stretch Out" boots, picture #2. Red and black are great holiday colors. Just imagine adding a white beard, a wide black belt with a big buckle, and saying “Ho Ho Ho”. (Sorry about that) Are these pictures from your new house? I really appreciate the character of older homes.

I dream of a world where chickens can cross roads without having their motives questioned.

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  • 3 weeks later...

Are these pictures from your new house? I really appreciate the character of older homes.

Yes they are! In fact, most of the pictures taken since August (with a couple of exceptions) have been in my new house. I have yet to get a "studio" set up, so the entry hall and front door (with the horrible curtains from the previous owner) have been my backdrop. Currently, I have the attic and second floor gutted and have been waiting on some help to get the ceilings in the rooms. I can do most of the stuff myself, but dry-walling ceilings is more than a one man job. I have thought about taking some pictures in the empty rooms (construction site) as a backdrop, but we will see...Thanks for asking!

Typically, I like to wait to post several outings at one time, but the last two days have been pretty remarkable, so I didn't want to wait to share them. Thinking about them, there were some real high points, but nothing too out of the ordinary. My outfits were OK, but not the best I have ever put together, I did pretty typical things, and it was very (read VERY) cold. What made them remarkable was how I felt, which is tough to convey in writing. But I really want to give it a try!

Monday January 4, 2010 - It had been a few weeks since I had a chance to get out in heels. The weather was not good, the holidays were nice but chaotic, and I had a bit of a nasty cold, so I was not able to make any rounds. Even though the weather was even worse (temperatures in the 20's F and a lot of lake effect snow) I had to get out again. I wore a fairly simple outfit - an oatmeal Gap sweater, Limited 917 bootcut jeans, black tights, and red Nine West "New Dealer" ankle boots. With my red boots exposed to the world, I headed out.

My first stop was my bank to check the damage Christmas did to my back account. With all of the ATM withdraws, I had lost count. The results were as bad as I suspected. Anyway, the tellers were very nice, we chatted about their New Year's Eves (I stayed in with my girlfriend - yes its official HF may be settling down) and the weather. No mention about my boots, though when I was leaving I looked back and saw all three of them rubbernecking for a better look.

Next I was on to the South Hills mall. I had a coupon for $25 off a $50 purchase from December when I bought my skinny jeans and this was the first day that I could use it. When I was in before, there was a gray, knit, turtleneck sweater dress that I truly loved. However, it was marked $60 and I couldn't justify the purchase at the time. I even tried it on and loved it. When I found it, they only had a large (I wanted the XL) but it was marked down to $30! To make the other $20, I found a pair of 312 bootcut jeans and a pair of black ankle length chinos. I asked the clerk - a very hip older lady wearing a black jumper dress, tights, and great boots if I could try them. Without hesitation, she took me to a dressing room. The large dress fit nicely, though a bit snug. I didn't care I was buying it. I also bough the jeans and the chinos, and with my coupon I got it all for $30! I chatted with the clerk, who was very supportive and courteous and headed on.

My next stop was Macy's. Though I have sworn off buying shoes at Macy's, it is still fun to look. The clerk there went in the back to look for any size 11 heels that were designated for the clearance rack and brought out a few for me to try. Just as in The Limited, I got a few initial shock reactions from people, but after they saw a guy trying on shoes, they more or less went about their business. I have taken to looking people in they eye if I catch them staring too long and saying hello. I only do this occasionally, because most of the time I simply am doing what I came to do. Let'em stare I say! Macy's really didn't have anything I liked, but I did head to the hosiery section to get another pair of the HUE body shaping nylons - this time in an ivory shade. The service was less than to be desired, and I did get a strange reaction from the clerk checking me out. But I got my nylons, which was what I went for anyway.

After Macy's I went to Aldo, where the manager was happy to see me. She went in the back and brought out all 4 pair of 11's they had in stock without even me even as much as asking. The store began to fill up while I was there and again customers looked, saw me, got over it, and went about their business. I was really tempted to but a pair of silver evening sandals complete with rhinestones, but my better senses prevailed. They just looked so damn good on my feet. The manager even drought me a matching clutch and was giving me ideas on where I could wear them. I almost said that I would wear them when we went out to dinner (a tribute to kneehighs), but I am trying to be a committed man right now. Besides she might have agreed and I would be out $75 for the shoes and the clutch...

I strolled the mall a bit more, getting lots of looks, giggles, etc. I went to JCrew and Banana Republic, but their clearance isn't my idea of clearance. At Ann Taylor, I really wanted to a pair of black slim fit jeans, marked down to $15, but the clerk didn't think that it would be OK for me to try them. The store was busy, but if I can't try it there, I am not buying it there. Plain and simple.

After the mall, I went to the Galleria, a shopping center about a mile away. I had a bowl of mac and cheese at Panerra Bread - which I found exciting on such a miserable day - though $5 for mac and cheese is CRIMINAL. I got a lot of attention from other customers. I set next to these two women who were both wearing pumps without hosiery, which I found amazing. They both looked at my boots and reacted with shock, but not as much as I did thinking about shoving a bare foot into a thin shoe when the ground is covered by snow. I did walkabout the restaurant to refill my drink, go to the restroom, etc. to give as many people a closeup look at my boots as wanted it.

My final stop of the day was a consignment store called the Avalon Exchange. I know that there are more than one of these stores in Pittsburgh, so for all I know its a national thing. They sell fairly good labels and even come couture stuff. I did try on a pair of barely worn Jimmy Choo slides, but there wasn't much in my size since the store tends to cater to young women. Again, I did draw my fair share of attention from the staff and customers. When I was walking back to my car, this guy with like 4 teeth gave me a very nasty look. It made me think that this is they guy everybody is worried about when they are so concerned about what "society" thinks. Lowest common denominator is simply another word for society.

All in all Monday was great because I spent nearly 6 hours out and about - or only slightly longer than it will take to read this post...

Tuesday January 5, 2010 - Again, snow and cold. It is as if I am living on the set of "The Road," which I guess I am since a lot of it was shot not far from me. And I think I saw one of the cannibal guys the day before. For my outing, I wore a burnt orange Izod sweater, the black ankle length chinos that I bought at The Limited the day before, and my Enzo Angiolini "King" lace-up boots. The pants were short enough that they gave a great view of the boots, which I have yet to wear covered in any way.

I started by going to the South Side Works, a trendy shopping area where there is a Steve Madden store and a Nine West retail store. I had to park fairly far away, but the walk was nice. Since it was windy, most people walk with their heads down. When I passed them, they would get a full look at my boots, then look up. I would then speak to them or wink, always with a smile. Sometimes they smiled back. At Steve Madden, I trued a couple pair of pumps in an 11, of course they were too small. The clerk was helpful and didn't even bat an eyelash while helping me.

At Nine West, I tried several pair. A very helpful young woman wearing cute boots and fantastic lilac lace tight (that I made sure to complement her on) brought me half a dozen pair to try. When I went into the store there were no customers, but while I was there about 15 people came in and it became very crowded. My favorite interaction was a woman shopping with a young girl, possibly grandmother and granddaughter. The older woman kept pushing the younger woman toward a pair of shoes that I was trying at the time. They were fairly conservative and I wouldn't think a teen would have liked them, but I could hear the grandmother say that look how good they look on him, his shoes are great, etc. When I was closer I interjected that they were also quite comfortable and could be worn with a lot of outfits. The grandmother reacted quite well - the younger woman was not impressed. I did but a pair of pointy toe d'orssay style pumps with a 2 inch heel - on sale for $20.

After Nine West, I wandered around the other storefronts - all of them either target toward people with more money than brains or twenty somethings. When I passed the last store and had to turn around, the clerks in a juniors store (one male one female) saw me. When I passed again they were at the window checking me out. I thought about going in, but something remarkable happened. A car slows down, and a large African Amrican gentleman rolls down his window. He says to me "I have so much respect for you and what you are doing!" I thanked him and he drove off. Now that's a positive reaction!

I headed to another shopping area called the Waterfront. There I browsed Macy's, but really only to warm up and use the restroom. I visited Lane Bryant, but even though they were having a big sale I think I have moved past the LB phase. I went into Ulta to see if I could get a makeup consultation, but there was nobody in the front of the store. Finally, I headed to Ann Taylor to see if I could get better service at this store. The clerk who helped me, again an older lady, let me use the dressing room. I did get two pair of the slim fit jeans - one in black and one in gray. She was very open minded and treated me very well. While I was shopping, a young woman followed me around with her cell phone. I am beginning to think cell phone cameras should be outlawed. But I made it very difficult for her to get her picture. If she asked I would pose, but I hate all of the sneaking around already! When I check out the clerk told me to come back and that I should feel comfortable in the store. Quite the contrast from the Ann Taylor the day before.

My final stop for the day was the grocery store. I didn't even hesitate to stop, not that I hesitate much any more. For me, I know now that I have reached a point where I simply don't care how people react or what they think. I did my business, even chatted with the woman behind me in line at the checkout. However, another person with a cell camera wandered by. I think in the future, I am going to say something when people do that...Look for me somewhere on the Web, I guess.

Those were my first outings of 2010! I will be getting out more this week, though I have met my fashion budget for the month. Anyway, like I said these outings were remarkable in how I felt. Is it possible that heeling is the path to enlightenment?

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When I passed again they were at the window checking me out. I thought about going in, but something remarkable happened. A car slows down, and a large African Amrican gentleman rolls down his window. He says to me "I have so much respect for you and what you are doing!" I thanked him and he drove off. Now that's a positive reaction!

Hmm! Maybe that was the same fellow who complimented me on my long denim skirt back on Veteran's Day. HA!

However, another person with a cell camera wandered by. I think in the future, I am going to say something when people do that...

Perhaps say, "Make sure you get my good side!" Heh!

Anyway, like I said these outings were remarkable in how I felt. Is it possible that heeling is the path to enlightenment?

Well, enlightenment comes in many ways and many forms to many people. If that works for you, then, by all means, sit back and enjoy!

I don't want to LOOK like a woman, I just want to DRESS like a woman!

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Here are the rest of my outings from last week...

Wednesday January 6, 2010 - Though it was still bone chilling cold, I really wanted to go out in a skirt. I wore white turtleneck sweater, black Lane Bryant slightly below the knee skirt, black opaque tights, and an old pair of (cheap) Areoslole boots that I forgot I still had. This is the first pair of tall boots that I ever bought and they do have a bit of tread on the soles for the slick sidewalks.

My plan for the day was to visit a couple of consignment stores, including the one where I consign some stuff. My first stop was one that opened before the holidays were I had a wonderful interaction with the owner - a cosmopolitan, petite, women in her 30's. Of course, she wasn't in when I stopped, but I did chat a bit with a couple of the women working and tried on a pair of tan leather pants. Though I didn't buy them, I may go back and get them later.

Next, I stopped at the store where I consign, but it was closed for the week, so I didn't get to visit the owner there either. I headed on to the outlets where I went to Lane Bryant and Nine West. LB just never has anything I really like anymore, and at Nine West I tried on some shoes and chatted with the employees more than anything else. I hit the Banana Republic outlet where every clerk working came by to see if I needed help, but seemed to be just checking me out. They were all very friendly however.

Finally, I stopped by one last consignment store. I tried on a leather skirt there which was way too small. The staff was nice, but really didn't pay me much attention.

Thursday January 7, 2010 - Though it wasn't a true "high heel" outfit, I really like the "freestyle" look of my first Thursday outfit. I wore a black turtleneck under a Rue 21 gray and black pullover, my black Ann Taylor slim fit jeans, black patterned tights and Nine West "Salty Sea" loafers with a 1 inch block heel. They are quite low cut and with the slim jeans, the entire shoe is exposed and shows the pattern of my tights quite well.

My first stop was to the bank. I had lost my ATM card the day before while out skirting and needed to cancel it and order a new one. I have been going to this branch for a few months now, and always in heels. The tellers are very nice and I think expect to see me in something exotic. Well, since I had all of this business to do, I was in the bank for a while. The teller I was working with recited my "pending" charges - Ann Taylor, Nine West, and Nine West Online and of course I said they were all my charges. She gave me a temporary card and said that I could only use it in ATMs. I said that I had done too much shopping as it is. Then I started talking to all of the women working about shopping. I told them that I bought my jeans at Ann Taylor for $15 and about some of my other sales. The never batted an eyelash as they shared shopping stories and even asked me if I owned a pair of Uggs to wear with my slim jeans. It was a great deal of fun and I am pretty sure that everybody is cool with a guy in heels.

Afterward, I went to Starbucks and relaxed. I read some in a wingback chair, drank a grande cocoa and listened to music. I sat next to a cute young woman who was reading as well and had brief interactions with her and a couple other customers. It was a nice way to spend the afternoon.

While at Starbucks, I got a call reminding me of my pedicure appointment that afternoon. Since tights make it difficult to get to my feet, I went home to changes. I put on a pair of brown footless tights, my Limited 917 bootcut jeans, and decided that even in the cold and the snow, I was going to wear heels to the appointment! I had chatted with the stylist about heels on numerous occasions, but I thought I would let her see me in them. I chose an understated pair of Bandolino "MacDougal" loafers in brown patent...block heel, safe for wearing to cross the street, but still obviously heels.

She noticed immediately, of course, saying how cute they are and that I will "break my neck" wearing them. We chatted about clothes, etc. and she was pretty cool with the whole thing. Of course it was too cold for flip-flops, so I sat in the salon for over an hour waiting for my nails to dry. She cam out an put my shoes on me, again saying that she can't beleive I wore heels in the weather we were having.

Friday January 8, 2010 - I didn't think I was going to have time to go out on Friday, but I finished my work early, and threw together a fairly nice outfit. I wore a brown Chaps sweater, brown Lane Braynt "Houston" dress trousers, and brown Franco Sarto "Mill" boots, with a small heel. I returned to Starbucks from the day before. Again, I read and had a cocoa. I chatted breifly with a woman about my age and even flirted with a woman in a sweater, dress slicks and square toe, block heels boots. She said that she bought them a Sacks last winter, but alas made no mention of mine.

Well, there you have it...my last four outings! I thought about going out today, but I am just sick of the cold! Maybe tomorrow....

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Greetings HappyFeat :-)

Great outings wearing shoes despite the cold weather.

Lucky for you the women at the pedicure put back your shoes for you !

Wondering if my girl at the pedicure would do the same for me if I wear shoes ?

Did not have a chance to try it since I only go there in the summer wearing gladiator sandals.

(I guess it would be too hard for her to put the strap in the proper hole...)

Maybe next time I wil try wearing regular shoes instead of sandals and see what happens :blinkbigeyes:.

My choice this time is for outfit # 1 and # 2. Again,well done !

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Yo, HappyFeat! Great pics all! I'm sure you're probably tired of hearing this from me, but your fine sense of style shines through yet again. And since I'm so predictable, I'm sure you know I've leaned towards pic #1 as my fave of the bunch. Your outing reminded me of last year around this time when I wore a short skirt and boots on a bitterly cold day. BBRRRRR! And then some! :blinkbigeyes:

I don't want to LOOK like a woman, I just want to DRESS like a woman!

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Nice outings, HF. I personally like Outfit #3 with the heeled loafers and flaired jeans. I think that look, with a pair of trouser socks, would be hardly noticable in most places. I am curoius as to where you may be headed, however. You've been wearing skirts quite abit, and have discussed getting make-up done a few times. Are you thinking of going the full cross-dress route in the future? While I am not in your league when it comes to heeling, I always thought that if I really wanted to be out in public in heels, and I mean feminine heels now, that I would feel more comfortable doing it in a full feminine appearance (though I certainly don't make a good looking female based on a few Haloween outings that I've had!...lol). So I just curious where you think you are headed. And I take it the new love in your life is fully aware of your clothing preferences? Tell me to mind my own business if I'm being just too damn nosy! I would certainly have that coming after asking such personal questions! But damn, I am curious yellow!

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  • 2 weeks later...

snip...

Lucky for you the women at the pedicure put back your shoes for you !

Wondering if my girl at the pedicure would do the same for me if I wear shoes ?

...snip

Actually, she is the first stylist to put my shoes on for me. She is very conscientious about her work and hats when the paint gets chipped or smeared prematurely. Typically I wear flip-flops, so she always offers to put them on for me. As far as your stylist, all you can do is ask!

snip...

I am curoius as to where you may be headed, however. You've been wearing skirts quite abit, and have discussed getting make-up done a few times. Are you thinking of going the full cross-dress route in the future? While I am not in your league when it comes to heeling, I always thought that if I really wanted to be out in public in heels, and I mean feminine heels now, that I would feel more comfortable doing it in a full feminine appearance (though I certainly don't make a good looking female based on a few Haloween outings that I've had!...lol). So I just curious where you think you are headed. And I take it the new love in your life is fully aware of your clothing preferences?

Tell me to mind my own business if I'm being just too damn nosy! I would certainly have that coming after asking such personal questions! But damn, I am curious yellow!

No why would I tell you to mind your own business? I do post things here for people to read to not only share my experiences, but to aid my evolution as a freestyler/heeler/etc. That being said, people just need to ask the right questions.

It is not my intention ever to go out in full female mode. I love being a guy and have no desire to pass for anything other than a guy. I do love seeing how far I can go and love to try new things, so I am always trying to expand my experiences. I could never pass anyway, since I do keep my facial hair all the time and being a large man, it just doesn't seem practical. In a few occasions, I have been approached by people about performing in a drag show from time to time, but that would be more about playing a role anyway - at least for me. Though I have been tempted, I have never seriously considered it seriously. I do think it would be fun to get my makeup done just for the experience, just as I do other things like getting full-color pedicures.

And yes, the love of my life does know about my tendencies. On occasion, I have worn a skirt around the house with her, she washes my tights and borrows my kneehighs. We have gone shopping together and even shared a dressing room on occasion. I have even worn heels with her when we have gone out. However, I haven't shared this Web site with her mainly because of the sorted details I have shared. She is a bit jealous, even of things I did prior to the start of our relationship. I do hate keeping secrets, but I have been rather open here...

Hope that answers your question. Please don't ever be afraid to ask anything - I don't mind answering.

Now on with the outings/outfits:

Tuesday January 12 - After work I decided to stop in a Starbucks to do a little computer work. My outfit was simple - wool blazer, gray/blue turtleneck sweater, Ann Taylor slim fit jeans, Nine West ankle boots with a block heel. I sat at a table next to a couple of women in business suits - both wearing nice shoes who both kept glancing my way. AN older couple next to me (the guy was rather uncooth) were having a heated argument (even in hushed tones) and he shot me a very strange look when I left. Afterward, I went to Barnes and Nobel where I sat in an easy chair and read a book. When I went to the restroom one of the clerks was wearing killer red pumps - patent, platfotm, stiletto - so I made a point to complement her on her shoes. She thanked me with a big smile. Later she kept walking by me and I always took note, exchanging a few positive glances. The bad part of the outing was I lost the heel tips on both boots and I am deciding whether to get them repaired or not.

Thursday January 14 - Another brief outing after work. I wore a gray wool blazer, burgundy Claiborne pull-over, Limited 917 slim jeans, burgundy knee high stockings, and black Nine West "Appaladay" loafers with a small stiletto heel. The bank tellers are very aware of my heels, and though they e=never mention them, they are accepting. The transactions went smoothly and I chatted with the for a short time. Next, I went to Starbucks near my house that I am going to try to visit regularly in heels. I did get a couple of looks, but nothing happened beyond that.

Tuesday January 18 - Another visit to Starbucks near my house. I wore a brown corduroy blazer, Claiborne turtleneck sweater, Limited 917 boot cut jeans, and brown oil skin Nine West "Geranium" loafers. I did get a look or two from an older woman who eventually struck up a conversation about the book I was reading. I exchanged glances with a woman in a nice business pants suit and boots a couple of time while she waited for her order. Later a couple of older guys sat down across from me and talked a few decibels too loud, but I finished my drink and headed home.

Thursday January 20 - My skirt outing for the week! I went short, very short for me. The weather had warmed up a bit, so I decided what the hay. I wore a Ralph Lauren cable knit sweater with brown suede patches on the elbows, a denim miniskirt, brown tights, and brown Nine West Mary Jane pumps. I planned on doing a bit of shopping, but my main consignment store was my only stop for the day. The first highlight of the visit was meeting a woman in the shoe section. She noticed me pull down a pair of snakeskin boots and told me she thought they were fabulous. She watched me try them on and told me they looked even better on. I wound up buying them for $6, a Payless brand I think. I found a couple pairs for her and she tried them on. We talked about shoes, styles we liked, etc.

After she left, I talked to the owner. She was telling me how she was so amazed that in my last visit, I talked to everybody in the store. She said that at first she was worried that people would be rude to me, but she said that every time I came in people were drawn to me. I found a couple of cool items like a long top that would go great with leggings and a brown dress that I am waiting to come down in price. I modeled the dress and spent over an hour wearing it while the owner accessorized it and found other things to go with it. I did look fabulous in it, I must say. The owner and her assistant (a teenage old girl, who was having too much fun) kept telling me how great my legs are. I also got a set of faux pearls for $4 that I may play with as well. Way too much fun!

Friday January 21 - I "stolen" outing for me. I really didn't think I would have a chance to get out, but as luck will have it, I got to put on heels. I wore a brown turtleneck sweater, brown Ann Taylor gauchos, brown tights, and brown Nine West "Gaffer" pumps. I went to a consignment store that opened about six weeks ago near my home. The manager there is fast becoming another person who I love to visit. She is a petite brunette with great style and a thing for sexy flats, skirts, and high end tights. I bought a pair of suede leather jeans and a satin skirt in brown. There is another pair of leather pants that I may go back and get. I tried on a silk Talbots dress with a jacket, that was still a bit pricey, but I did look good in it. I may get it. After checking out, I chatted with the manager and clerk for over an hour. They both loved my shoes and the clerk brought me a pair of Dolce and Gabana clogs that are just a bit small. However for $20, I may need to get those as well. Again, another wonderful experience. Just a lot of fun...

The pictures are of my outfits. The last two, I took advantage of a couple pieces of drywall setting near where I take my pictures to make a "backdrop." When I do my studio, I may just have to make a drywall backdrop...

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Style is built from the ground up!

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Wonderfully arranged, as always. I particularly like the first outfit and the last one. Thanks for the reports and pictures. :blinkbigeyes:

Being mentally comfortable in your own mind is the key to wearing heels in public.

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