HappyFeat

Not bad, HF! Not bad at all! I might have to try girl's jeans myself! Might be fun!

I have noticed that more and more of my outings have been while wearing jeans, and that hasn't been by design - it just kind of happened that way. Most of the time while I am out shopping, I head right for the jeans to see what the stores might have. In some ways, jeans are the "new" heels for me. Besides, I think nothing makes a pair of heels look better than the *right* pair of jeans. Unless of course it is a great skirt...LOL

I would suggest investing in a few pair of nice girl jeans and just see where it takes you.

The closest that this ever happened to me was I ran into a former student of mine while I was out in a pair of patent loafers. Nothing was said and the few time I have seen him since it was never mentioned.

After giving this some thought, I realized that I really don't have any close guy friends anymore. Most of the people I associate with are either women or at work, where I try to keep my personal life, well personal. Of my woman friends, several know that I wear heels, but not all of them do.

Glad to see that you are still getting out and about! You are still a true inspiration.

Heeling on vacation is quite a bit of fun. Glad you had a nice time away and thanks for sharing! I do love reading your adventures.

Congratulations on your first time out in heels! Makes you wonder why you never did it before, doesn't it? If you are going to own great shoes, you might as well show them off. Here's hoping that there are many more outings in your future.

Here are some more jeans that I bought recently. Aren't sales grand? #1 Calvin Klein Straight Legs from a thrift store, $7. #2 New York & Co. Straight Leg gray from the retail store $6. These are pretty low quality and I am not crazy about them. #3 Tommy Hilfiger blue "Hope" boot cut jeans from Macy's $10. I have the same pair in black. #4 J. Crew Vintage Slim from the retail store $15. #5 Banana Republic skinny ankle length $15. Don't yet know about these but they do have some possibilities. I probobly wouldn't wear the shoes in the picture with them, maybe something a bit lower. In all pictures, I am wearing Nine West "Hotone" carmel peep toe sling backs. Some of the shots have the cuff of the jeans doing that sling back thing...LOL Finding great bargains on jeans right now is not that difficult, so it is a great time to look for new and different options.

HappyinHeels, I can't agree with you more that the in store experience at Charlotte Russe is outstanding. They often run major sales as well. Unfortunately, they only seem to go up to a US10, so I have never actually been able to find a pair there that worked. However, all of the associates are very helpful and very nice.

Here are some of my recent purchases. Most, if not all of these fall into what I would call the "boring" category. However, I have been trying to diversify my collection a bit since I am wearing heels more and more these days and was looking for things a bit more conservative. Not every outfit works with over three inch heels, at least not for me...

Easy Spirit "Taciash" wedge slides: a nice pair of basic black wedges slides to be worn with shorts, capris, etc.

Bass "Cecile" loafer mules: These go great with jeans as well as capris.

Xhileration "Saniya" faux black patent flats: I know that this is a high heel place, but flats are an important part of my evolving look. These would be fun for shorts especially. Plus I have always wanted a pair and for $8 at Target they are a can't miss.

Unlisted "Young Spirit" brown multi pumps: Found these at a Shoe Department store for $15 and my wife loved them. They are just fun looking shoes.

Nine West "Ochen" gray pumps with kitten heel: Bought these to wear with capris and possibly skirts. Low heel, but still a pretty sophisticated look.

Very interesting links/pictures! What I think is most amazing is that the comments in the first set were quite positive (for the most part) and since my one semester of German was quite a while ago, I am not so sure about the second one. I think the pictures show an alternative look that is still quite masculine and really works. Gives me a lot of ideas for the future...

Like your Saturday night outfit. You look great in those sexy red sandals.

Well done, my friend. Well done! As usual, you exhibit your own special brand of style that makes you stand out here at HHP! My favorite from the new batch of pics is number #4!

Like others have said the red heels pic is great. But any of the last 3 work for me.

...Personally, I love the look of those red sandals with the slacks and jacket. Your wife has great taste! ...

I couldn't dare pull off the red strappy sandals in your pic, and they are not quite my taste, but they still look nice on you regardless.

That's part of the fun with an item like red strappy sandals, their are risky, but can really give a pop to an outfit if done right. Obviously, they aren't for everybody, but in moderation I do love them. I have worn the quite a bit over the last few years and plan to get much more out of them. I have the same pair in black, that I wore in my last series of outings.

Part of my dilemma is that I really don't have many choices in sandals right now, and what I do have are mainly black. In some ways, black sandals seem a bit contradictory to me...summery in a non-summery color. But then again, black is ubiquitous. I am sure the red sandals will have another appearance or two before the summer is over, especially since my wife loves them.

... Your wife has great taste! Does she wear similar outfits? ...

She does dress nicely most of the time. She really likes it when we can coordinate our outfits since we do onw a few of the same garments, as well as shoes. What is really fun however is having another person to make suggestions on outfits because she may think of combination that I may not be aware of or things that I may be a bit nervous about trying. It is adding a whole new dimension to freestyling.

You really do dress to impress HH and I am invy of that! ... Thats just me, I always been a levi , jean and heel kinda guy but recently, I bought a pair of ladies jeans that I really like!

No need to envy me John! One of the things that I have discovered at HHPlace is that we all bring our different looks to the front. For example, JeffB's look with the skirts, etc. works great for him, but it wouldn't look natural for you. Levis and heels is a look you pull off magnificently - a macho guy in heels - which is a look that really doesn't work for me. So be proud of your style (which I know you are) and continue showing Canton how it is done. Though I have a feeling that your experiment with lady's jeans will open a whole new realm of heeling for you.

And as always, those Naturalizer t-straps look great. I think those are a nice choice, as the heel isn't ridiculously high, and the tickness of it looks good on a larger, male size leg (I'll never get over 4" spike heels, however, lol!)...

Like you, a stiletto heel will always catch my eye on the rack or in the store. But in my opinion, if you are wearing the heels with pants, the whole leg silhouette is reduced and if I am wearing a skirt, I don't figure too many people's first thought is that my legs look too big...lol The t-straps are a great pair of shoes and when people ask me where I got them and I tell them they are Naturalizers, they are shocked. I can walk for hours in them. Again, I am sure they will pop up a few more times this summer...maybe even next week.

As far as heel height, I am really on the lookout for more stylish shoes with lower or medium sized heel. The highest I have ever worn as still under 5 inches, so height has never been my major concern. Here is what I have found ironic: It is very difficult to find medium heels in a size 11 or 12! Higher heels are not that hard to come by. Again, I just find it a bit strange.

As a aside---we live close to the South Hills Village and are there often. It is also the closest to our home as it is for you. We MUST get together sometime and meet face to face both you and your wife and Mickey and I.

Absolutely! Kind of our own mini heel meet. I will be in touch when I can plan something. Right now, every time I make plans something comes up. But before the summer is over we will have a get together.

Thanks for the update Jeff. I think Capris are excellent to wear with tall boots, since you don't have all of that material to bunch around the ankles, etc. I am glad to hear that you are thinking of pairing them with pumps as well because I think it would be a great look for you. It gives the same kind of effect that your get from a skirt but also allows for some variation in your wardrobe. For me, I have found the variation is what is most fun about freestyling. Recently, I have worked Capris, crop pants and shorts into my rotation and have found it to be a great deal of fun. I am looking forward to seeing how your new outfits!

Here are some recent outings:

Thursday May 27, 2010 - My look for this outing was one that I have been experimenting with recently. I am trying to incorporate a more understated look into my rotation on occasion, just for a bit of variety. I wore a black and white knit pullover, white Ann Taylor knee length shorts, and black Bass "Kendra" sandals with a low wedge heel. Though it was a conservative look, it did feel great and was a nice choice on a 90 degree day.

My outing was a continuation of my trips to local shopping areas while heeling. I visited the South Hills Village Mall, which is actually the mall closets to my house. My first stop was New York and Company. The clerks are usually nice and do allow me to try things on if I ask. I tried on a couple of outfits, a one peice short outfit and a cotton dress. Neither complemented me terribly well, but it was a pleasant shopping experience. Next, I went to the Banana Republic. Upon entering the store, I was given a scratch off coupon that entitled me to 50% my entire purchase! My dilemma was that I was a bit broke, with payday coming the next day, so I decided to just "scout" the store. This store isn't overly accepting, but they do offer some help. I tried on several pair of jeans, a couple of skirts and a fantastic dress, all already marked way down. I knew that I had to make it back.

After BR, I went to the Limited. This store is always very helpful and glad to see me, even though I usually don't buy much. When I walked in I was greeted by one of the clerks who waits on me a lot - a tall, stunning, though large framed young woman. She is one of those girls who just isn't yet quite aware of how beautiful she is. As soon as I came in the store, I say that miniskirts were on sale and they had a great bright blue one. However, they didn't have a 14,, which was disappointing. After browsing the store and chatting, I was still drawn to that skirt and decided to try the 12. The clerk took me to a fitting room and when I tried it it fit like a glove. The other two clerks working each rushed back to see and were all amazed at how nice it looked. For the next hour, all three clerks brought me things to try and I modeled for them. It was way too much fun. However, all I bought was the skirt. After checking out, the tall clerk told me that they were doing a new floor set and that I should come back and see it, and that I should wear my new skirt when I did. I am hoping to make it back and do just that.

After spend more time at the Limited than I had planned, I had to call it a day and continue my shopping the next day - especially with the 50% BR coupon in my pocket.

Friday May 28, 2010 Afternoon - I returned to the same mall as the day before to complete my outing. I was not as understated as I was the day before. I wore a peach linen shirt, white JCrew "High Heel Flare" jeans, and Nine West "Rocco" d'Orday pumps with a very high heel. I wanted to look as summery as possible and my sandal collection is pretty limited at the moment.

Back at the mall, I went to Banana Republic and tried not only found the dress that I wanted, but another one that was quite nice, as well as an olive skirt that was also pretty sweet. I tried on all three items as well as a few others and bought the two dresses and the skirt. When I was checking out, the clerk was amazed that the dresses were as marked down as they were and when I gave here my 50% off coupon, she announced it to the entire store, "He got a 50!" We chatted a bit, she told me how she liked my taste, and it was a very nice experience. However, she forgot to take out one of the sensors so I beeped on the way out. Another clerk came over, went through my bag and found the sensor on my black dress. She said, when taking it back to the register, "This will look gorgeous on you!" When she came back, we chatted a little and I went on my way.

Afterward, I went to JCrew to browse. I found a great pair of distressed Matchstick jeans. The clerk, young African American guy took me to a dressing room and was very impressed by the fit. I browsed the store for a while and went to ask another clerk a question, and I was the one who was a bit shocked. I thought it was a girl, but when he turned around it was a young Asian man, wearing Capris, flip-flops, had his nails done, and long wavy hair. He was helpful in answering my question, but it was the first time I had ever encountered another guy in feminine attire while shopping.

Next I went to Aldo to find shoes to go with the skirt I bought. They had a pair to cute 2 inch thong mules in silver that I loved but they only came in a 9. The clerk offered me some other suggestions, but nothing I was in love with. I decided to try Macy's. I found a cute pair of yellow peep toe pumps that seemed to work. The clerk again was very helpful, listening to what I wanted and even brought me five pair or so in my size for me to try. Though none were fantastic, I did buy the yellow peeps.

My two days shopping at SHV Mall were fantastic. Some of the best experiences that I have had yet and a definite A+!

Friday May 28, 2010 Evening - Date night! My wife actually picked out this outfit: purple and white striped shirt, black Tommy Hilfiger "Hope" jeans, and purple Nine West pumps. We ran a few errands early in the evening, and of course I got some attention. We went to dinner at our favorite Mexican place where the waitress told me how much she loved my shoes and we went to a wine bar and relaxed and chatted. Again, I got a lot of looks but no comments there.

Saturday May 29, 2010 - Date night 2! We went to dinner at a fancy seafood place and then to see Sen and the City 2. Again, my wife picked out my outfit: A blue double breasted linen blazer, a crinkly white shirt with french cuffs and brass cuff-links, Limited 917 boot cut jeans and red Nine West "Tomcat" sandals - just Sex in the City enough for her. At dinner the only strange experience was from a couple that came in toward the end of our meal. The guy just kept staring at my feet, I think desperately wanting to say something. His date glanced, but could of cared less. It was interesting at first but actually became a bit creepy after several minutes. At the theatre I did get a few gawks and long stares, but nothing too out of the ordinary. Date nights are so much fun in general, but wearing heels with my lady makes then so much better.

Tuesday June 2, 2010 - Another shopping outing. Though the weather was nice, I am so disappointed than most of my open shoes are black. But I had to go with what I had. I wore black t-strap Naturalizer "Amanda" sandals, gray Banana Republic jeans, and a light blue dress shirt. I went to the Mall at Robinson to check out Aldo primarily. They had the sandals I loved in a 10, but were still a bit too small. When the clerk looked for them online, they were sold out in an 11. I went to Banana Republic to see if the dresses I bought were cheaper, but ended up trying on a couple pair of straight leg jeans on sale for $12 each. The clerks at this store were quite helpful and friendly, even looking for size 11 shoes. I bought the jeans, and browsed a few other stores but nothing really caught my eye, even at Baker's where the clerk brought me half a dozen pairs to try. All in all this experience merits a B, but I will try it again in the near future.

Attached are my outfits for these outings.

I am pretty sure somebody has taken a picture or two, based on the number of cell phones I have seen people pointing in my direction. However, the one thing I am fairly certain of is that taking action shots with a small camera or a phone in low light would not usually give good results, so I just don't worry about it.

My latest purchase. A reward to myself for completing a 12 week very strenous excersize program I designed for myself. Took off almost 20 lbs and gaind about 4 lbs of muscle. All natural.

I think I deserved a new pair of shoes or 2.

What a great reward for great results. Congratulations on your weight loss and new muscle mass. That is no small undertaking and I know you take weight training quite seriously. The shoes are fantastic, and I love the zipper back. They look like Aldo to me, but where did you find those babys?

HF, nice choices! It would take a lot to get me out in that yellow pair! lol

Well, the yellow shoes will be the least out there part of the outfit I am planning. These are the first pair of shoes (of the hundreds that I seemed to have purchased over the years) to go with a specific outfit - a bright blue skirt. So stay tuned for how they go over...

I am not really a boot person, though I do have several pair as staples of my shoe wardrobe. My thought is this...if you are a man wearing heels, you are already pretty much the exception to many fashion rules, so if you can take the heat, love your boots, make them work for you...

As a resident of the fine city of Pittsburgh, I would actually buy the over priced rink side tickets at the new arena to see him wearing those! Though, I don't think Mr. Crosby and I heel in the same circles since I have never bumped into him shoe shopping...

I find this entire discussion fascinating. Discrimination is a funny thing and can be very difficult to prove. It is common practice to not hire somebody or fire them for that matter and give grounds that are totally unrelated to anything discriminatory. Also, if you don't have the money to hire an attorney, you have no rights - at least in the United States, so the merits of the case and the shoulds and oughts are simply academic. In my opinion, American Eagle is an overrated, overpriced low end brand. In fact, this policy surprises me not because they are based in my hometown - Pittsburgh, which I have found to be one of the more close minded places that I have ever been. Ironically, the person who checked me out at Wal-Mart the other day was a fairly obvious M2F transsexual. Its bad when your company lags behind Wal-Mart in progressive hiring practices. Also, I was waited on at JCrew by a guy wearing Capri pants, flip-flops and red toes. That being said, I have been offered jobs at retail stores while I have been heeling. In fact, Nine West, Lane Bryant, Aldo (2 different stores) the managers each told me that I could work there and dress however I wanted. Now, I am not a transgendered person, but as a guy wearing heels, there are instances when some people are accepting. Even in the intellectual and cultural backwaters, far from NYC.

I just voted in the poll. I'll let you guys look it up

Actually Bubba, the UK doesn't compete in the World Cup - each individual country in the UK has a team and I think England is the only one who made it this time. The US plays England on the second day. The only reason I know any of this was that I have a friend fron Uganda, who will be in South Africa for the World Cup, who in 2002 taught me all about soccer because I taught him all about baseball. Now he also has season tickets to the Washington Nationals, so I don't think I did him any favors. However, I have season tickets to the Pittsburgh Pirates, which might as well be playing soccer.

ImInHeels, you are far from alone. I have my dream job, love the people I work with and have a huge amount of time off (including the next 10 weeks or so) but I still get the Sunday evening blues. I think it goes back to when I was a kid, having all of the school work put off until Sunday and knowing I could never get it done. Since I still work in education, my Sunday nights are often my catch up time and I always feel swamped. Who know... The singer/songwriter John Prine wrote a song called "The Late John Garfield Blues" about not being able to sleep on a Sunday night and watching old movies on TV (WAY before cable) and to him it seemed that the actor John Garfield was always in those movies. So, as I said you are not alone in this...

I almost never wear hosiery of any sort with jeans - particularly in warmer months. However, when I do I prefer trouser socks or patterned knee highs. On the flip-side, I would seldom wear dress trousers without hosiery and prefer pantyhose or thighs with such an outfit. For me, the difference is formality - jeans are more casual and nylons just clash too much whereas dress trousers require a more finished look. Besides, some of the skinny jeans that I wear leave little room between my skin and the jeans for anything else. In some cases they are tight enough to be leggings.

Your new jeans look great with your short heeled shoes. Love the color of the shoes. Curious---have you tried those new jeans with a higher heeled shoe to see just how they would look with them?

Dawn, the shoes I was wearing in the pictures are over 4 inches and are some of the highest shoes I own. I was actually surprised at how well they worked with the straighter/skinny leg jeans. Typically, I try to go with a lower heel for straight legs jeans to try to avoid being too over the top.

Great selection of jeans! And congrats on the weight loss!

Thanks! However, I am running into a bit of a problem. Some of even my newer jeans are fitting a bit looser than I like. I have a few more pair I may post in the near future that I bought recently that could also be approaching too big. I need to see how this weight loss thing is going to work out.

maninpumps, I looked up the shoes that you bought and they are FABULOUS! You absolutely must wear those when you find the right occasion, regardless of what you choose to go with them. They are simply beautiful. That being said, I think you could wear them with jeans quite well. As for tradition, your wife may be right about wearing satin shoes, however since you are a man, no matter what you wear them with would be unconventional. And I think everything goes with the right jeans. My suggestion would be a pair of dressier jeans, boot cut but not so long they cover the shoes. A nice length would be about a third of the way to half way over the heel while standing. A deep blue denim would be best, but not black. I was told by a clerk in a shoes store once that navy blue shoes are popular with women for jeans, which surprised me, but the jeans shouldn't be much darker than the shoes. I would suggest a crisp white dress shirt, maybe even starched, and a nice black jacket to top it off. Of course, your toes should be in nice order as well - not necessarily polished, but they are the final touch for great peep toes. I think it is wonderful that you have a supportive spouse who offers you advice and you can share your passion with. Maybe you should take her to a nice dinner in your outfit to show her how well you can get them to work with jeans. Good luck and let us know what you decide.

Here are three of my latest purchases:

#1 Bandolino "Shelly" peep toe pumps in yellow. This was the first pair of shoes I think that I ever bought to go with a specific item of clothing. I bought a fantastic royal blue above the knee skirt at the Limited and had been on a mission to find a great shoe to wear with it. My hear was set on metallic sandals, but these really caught my eye. A nice color and a fairly moderate heel. Got them at Macy's for $30.

#2 Nine West "Shardae" patent sling backs in brown. Found these on e-Bay, was the only bidder and got them for $15 including shipping. Though they are brown patent, the appear more eggplant in the right lite. They have a nice square toe and are a bit on the conservative side, but I think they will be a fun shoe to change it up every now and then.

#3 Circa by Joan and David suede sling backs in black. Found these in a consignment store for $10. They may have been worn once. The leather soles show very little wear and there was an original price tag from Macy's saying that they were originally $89. The heel on these is to die for. I may wait until fall to wear these babies, but it will be worth the wait.