The Importance of Preparation

[JeffB]

When people here at HHP, or complete strangers on the street compliment me on my attire, that makes me feel proud because I didn't arrive at my appearance by accident, it's the direct result of lots and lots of preparation. Prior to each and every outing, without fail, it's not uncommon for me to spend upwards of an hour, sometimes longer trying on a variety of clothes in order to put together just the right outfit that will both compliment me and make me look my very best, my one and overriding goal. Even when I was just wearing heels, I sought to pair my footwear with the sharpest, most stylish clothes possible, I mean, what self-respecting person WOULDN'T want to look their best when out and about in public? And now that I've made the decision to wear skirts full time on all my outings, that need to look my best increased tenfold because I'm wearing clothes most associated with the fairer sex, therefore, I have to present the best, most tasteful and stylish image possible so people don't look at me like some sort of oddity. And arriving at that desired image takes a considerable amount of work on my part. Like I said, it's a regular routine for me to spend an hour or more before my outing trying on various combinations of tops, skirts, hosiery, shoes (or boots), belts, jackets, even handbags, scribbling down notes here and there as I seek to assemble just the right outfit that I like and would flatter me in just the right way when I go out in public. Only when I'm fully satisfied that I have put together just the right outfit that I like, do I head out the door. Having gone one step further in my public fashion freedom exploits by wearing skirts, it's absolutely crucial that I look nothing less than my very best, I have to present the best possible image so I'm not seen as some sort of freak because I'm wearing women's clothes. And it's only through lots and lots of preparation do I achieve the image I seek to put on display before the public at large, regardless of if said public chooses to acknowledge me or not. Whether you just wear heels, or heels and skirts like I do, you can't, and I repeat, CAN'T just throw on whatever strikes your fancy and head out the door without taking the time to see if what you wear looks good on you. If you don't, you run the risk of attracting the sort of attention you might not want, having passersby give you funny looks or giggle or even laugh on you if you don't look right. Of course, that happens to us freestylers anyway, no matter how well you might be dressed, and yeah, that's happened to me as well, but that shouldn't stop you from doing the required preparation to craft your style and display your best possible image to the world. Sure, preparation can be boring, even hard work, but it can produce delightful results when someone who doesn't know you from Adam walks up to you and tells you that you look nice. Then all your hard work will have been worth it, and more. So remember, people: preparation is everything!

[LovesHiHeels]

I very much agree wilth what you say there. Once you start wearing skirts out in public you then need to find the right top to go with the skirt, which in my cause it not always easy. There is always going to be people out there that are going to giggle or say rude things to you, no matter how well a man looks in a skirt.

[roniheels]

JeffB ... I could not agree with you more! Sometimes I take a day or two thinking about my outing and what would be best to wear and what high heels to wear with them. As I have stated in many past posts, I prefer wearing a man's suit with my high heels (this was inspired by many women who wear high heels with their pant suits). Recently I wore jeans with a shaker sweater and my thigh boots, but i also wore an over-sized sport coat with it. But again, I always think at least a day ahead of what I might like to wear and what high heels that I own would go best with them. I really respect and admire the thought and effort you put into the outfits and high heeled footwear that you wear with your attire. I think the entire site appreciates your inspirations and posts.

[Tech]

Jeff No offence buddy, but all that time fluffing about and you cant see that the handbag really looks stupid???

[Histiletto]

Fashion? I've haven't really followed it, in the sense of updating to the lastest styles. Picking the items from the trends as they come and go that satisfy my idea of looking good is the extent of my in-crowding. Therefore, my choices for attiring aren't as extentive as other have implied theirs are. Preparation is still important, but my choices are decided with in a few moments before walking out the door. Perhaps, it's my lack of fashion sense or my social male breeding that makes me give so little time to looking perpect, but wearing my choice of footwear didn't include any extra sprucing up for others before reading the post in this forum. They say there are cycles to fashion and I like to see the better items come back. Like getting rid of the long to excessively long pointed toes. A personal preference I know, but that's what I would like to see happen. The shorter pointed toes are in keeping with the natural effect that high heels diminish the horizontal length of the feet. However, the squared or stubby toes don't appeal to me either. Picky, aren't I?

[kneehighs]

Personally, I don't think the purse really helps or harms Jeff's outfit. It's color is neutral as is it's design (especially when combined with a black leather jacket). Considering that bags are symbols of the person, it's ultimately up to Jeff, "what is he trying to communicate to himself with carrying his purse?" Is he trying to feel feminine for himself? Look feminine to others? One thing I think most guys here overlook though is they limit style to what they already know. What I mean by "what they already know" is the pieces that are already in their closet and the ensembles they already imagine in their minds eye. Go out and find some inspiration outside yourself. Browse the women's fashion magazine rack when you are at Barnes and Noble or Borders. Browse the women's magazines like Vogue, Harper's Bazaar, and ELLE. Most here would do well to browse Lucky, In Style, Glamour, and Cosmo as the aesthetic appeals to a broader base than Vogue, Bazaar or ELLE. Study style dot dom look books. Look for outfits you can duplicate or modify to your own personal liking.

[Bubba136]

Jeff

No offence buddy, but all that time fluffing about and you cant see that the handbag really looks stupid???

Tech.....are you taking piss-pills on purpose?

[Tech]

Tech.....are you taking piss-pills on purpose?

Not piss-taking at all, just an opinion. Are we all meant to follow like sheep and praise everything, regardless of what we think?

If any friend of mine spent an hour getting dressed, I'd wonder if he lost all sense of co-ordination.

Personally, I dont see how it takes somebody an hour to figure out what goes with what, but thats just me..

[Bubba136]

I think both JeffB's and kneehigh's comments point out the vast spectrum of tastes and purposes that members of hhplace present. Kneehighs presents a well coordinated image comprised of intermingling men's and women's garments for an "avant-garde" appearance, including high heel shoes. His tastes are on "the cutting edge" of fashion evolution -- All the while appearing as person that cares about the way he looks. His image, as I see it, tends to project co-mingling of styles and items of clothing that could be appropriately worn by either a man or woman without anyone taking offense at seeing "a man wearing women's clothing. It's about style, fashion and taste. JeffB, on the other hand, is like my wife. She carefully thinks through what she is going to wear based upon where she is going. She selects matching garments, shoes and jewelry that is appropriate for the occasion. When she walks out the door, one can take one look at her and immediately tell that she is a woman with great taste, a flair for fashion and tremendous confidence. JeffB is like that. Neat, clean and projecting an image of really caring how he appears in public -- regardless if he's dressed as a man for work or wearing a skirt and heels for an outing at the local mall. He appears to strive -- as he says -- to present himself in the best possible way to show that he cares about his looks and dress. Then, there is another category that HappyFeat fits into. He combines both of JeffB's and kneehigh's categories with great care, transforming them into his unique personal dressing style. He's not above adapting some of kneehigh's technique of mixing and matching items from both sexes -- while not as daringly as kneehigh does -- and, at the same time, making sure that his appearance projects the image of a person that cares how he looks to others. And then there are different type that are in between. I like to wear woman's shoes. It doesn't matter if they're high heels or not. Just as long as they are women's shoes. While I don't wear woman's clothing, I, too, care about my appearance. But is is infinitely easier for me to achieve my well dressed look because I stick exclusively to men's clothing (on the surface, that is). Carefully combed hair, neatly pressed, clean clothing, and appearing as the man that I am....only difference, you must look closely to see that I am wearing women's foot ware. Then all of the other combination's in between. Y'all can sort these out for yourself. But, what ever way you sort it out, there is no denying that all three of our "role models" are in a class by themselves and one that more of us should strive to emulate.

[Bubba136]

Not piss-taking at all, just an opinion. Are we all meant to follow like sheep and praise everything, regardless of what we think?

If any friend of mine spent an hour getting dressed, I'd wonder if he lost all sense of co-ordination.

Personally, I dont see how it takes somebody an hour to figure out what goes with what, but thats just me..

There are some women out there that can put JeffB, HappyFeats and Kneehighs to shame when it comes to taking time "getting ready" to go out.

If you're married, take note of how lucky that your wife doesn't take as long as JeffB does. LOL

[kneehighs]

^ Interesting analysis there Bubba. I spend more time studying and observing how the leaders of the fashion world dress (androgynous dressing female editors), than I do rummaging through my closet to make an outfit. Making an outfit takes about 5 minutes, since I already have a clear picture of which outfit I'm attempting to emulate. Those movers and shakers of the fashion world are literally the trend creators, the pinnacle of the fashion media elite. They are fortunate because they get their Balenciaga or Balmain leather jackets for free or for a deep discount. Style may be important to me, but it's not worth 10K for a leather jacket. The point is that I take my cues from those that are better at style than myself. I look outside myself for influence and then adapt it for my taste and closet limitations. Staple pieces like knee boots, a bag (in JeffB's case), a leather jacket...pieces that will last years...I justify spending big money on because they are "investment pieces" A good women's leather jacket from Rick Owens, Kenneth Cole, or Cole Haan is an investment piece. It'll last for years.

[spiker]

Jeff

No offence buddy, but all that time fluffing about and you cant see that the handbag really looks stupid???

As always Tech, you really do have a way with the words!

Spiker.

[JeffB]

Thanks for the responses on this topic, everyone. I feel that preparation is key, because if you look good, then you feel good, and when you feel good, you exhibit a positive presence that does nothing but help while in public. As for Tech and his comments, let's be charitable, everyone is entitled to their opinion, and that was his. Do I agree with it? No, but I respect his having taken the time to offer his viewpoint.

[HappyFeat]

After reading what has been posted so far, I thought I would chime in with my two cents. Some wonderful points have been made so far (thanks for the shoutout Bubba) and I agree with much of what has been said. First of all, let's take it easy on Tech. He keeps our little zoo going, and gruff though he may be, his advice he has offered me has been valuable. Though, I may not agree entirely with his (or any other post for that matter) it is honest and I always consider it when preparing. For me, preparation takes many forms. One of the great aspects of freestyling is watching what women wear. I love women and to be able to really appreciate a well-dressed beautiful woman is just a bonus. I have learned a lot from woman of all shapes, sizes, ages...pretty much any demographic group you could think of. It reminds me of when I played sports. I had a coach who told us that we could learn from any team we played, because no matter how good or bad they were, they likely did at least one thing better than we did. My coaches also insisted that we were our uniforms well, kept them clean and fresh. We were representing a school, community or what ever, so we had to transcend just representing ourselves. As Kneehighs suggested, I also look at magazines, catalogs, fashion sections in newspapers, etc. to get ideas on what I would like to try. This goes for both "men's" and "women's" items. I tend to be a sharp dresser (at least by my community standards) all the time. I take pride in my appearance and always want to put forth an image that is on par with my personality. I also prepare by doing quite a bit of shopping. I don't always buy (I know that comes as a shock to many of you) but I do like to see what is out there and try it on for fit. I have been pleasantly surprised about how many options there are for fashion. Usually, my preparation is done well in advance of an outing. I know what I have in my wardrobe, and build my outfits in my head before I start dressing. Of course, there are times when I change my mind, try other things, etc. but usually I know what I want to wear well in advance. I also try to vary what I wear based on where I am going. If I go to the same places a lot, I try to wear different outfits. This takes a bit of planning as well. Another thing that I do is simply do what I want. I know that I don't always have the right body for the look i want to achieve, but I still try to give it a shot. If I want to wear a dress, I do it because I want to. In the end, it may not be a "perfect" look but I don't think I have ever been too far off. For me, freestyling is about risk taking and sometimes I don't get it quite right. Finally, I love posting pictures of the outfits that I wear. The feedback is invaluable, and no, I don't always look for simple praise. Of course, I don't look for simple criticisms either. Solid constructive feedback is very nice to receive and from time to time I find it here. I consider this part of my preparation as well since evaluating what I have done in the past helps me prepare for the future. Fashion has become such a huge hobby for me in the recent years thanks to freestyling. Before I joined this forum, I did plan outfits but it seldom went beyond wearing heels with my traditional wardrobe. I always liked to try new things and be a bit out of the mainstream, but now I have discovered so many options that I see no limits in what I may try. The bottom line is that it should be fun and planning a fun outfit and a fun outing is really what preparation is about for me.

[Tech]

As always Tech, you really do have a way with the words!

Spiker.

Indeed, I'm not exactly well known for being tactful, I'm just a "say what I think" kinda person.

As for Tech and his comments, let's be charitable, everyone is entitled to their opinion, and that was his. Do I agree with it? No, but I respect his having taken the time to offer his viewpoint.

Thanks Jeff, its decent to finally see somebody who see's it for what it is, its just an opinion, something we are all subjected to in life possibly many times a day by everybody we encounter, just not always a verbal one....

[SandalFan]

And then there are different type that are in between. I like to wear woman's shoes.... While I don't wear woman's clothing, I, too, care about my appearance... But it is infinitely easier for me to achieve my well dressed look because I stick exclusively to men's clothing.

Yup, I'm definitely more in line with this category of heeler.

Just recently, however, I got inspired to try adding a touch of glam to my appearance with makeup. The other day, discovered a band called Placebo. I found their web site, and was like, "Ooh, one of them looks kinda hot." Then I found out that person is their lead singer, a man named Brian Molko, and he looks absolutely gorgeous in makeup! Then I got curious and started Googling "guys in makeup," and holy crap! Then I started browsing makeup tip videos on YouTube, and got to thinking.

Suffice it to say, I am quite eager to start experimenting on myself, and I can't wait to see what I can come up with; preferably something tasteful that I can wear outside with my regular attire - black 4" stiletto ankle boots, black jeans, black T-shirt, and the occasional solid red or white long-sleeve Twill dress shirt, tucked in and unbuttoned down to my belt to expose my T-shirt.

My wife was elated when I told her, and is excited about helping me with makeup tips.

I've got a makeup mirror on order and arriving this Thursday.

Here's a pic of Brian Molko:

http://laurganism.com/wp-images/brianlips.jpg

[JeffB]

Thanks Jeff, its decent to finally see somebody who see's it for what it is, its just an opinion, something we are all subjected to in life possibly many times a day by everybody we encounter, just not always a verbal one....

Quite true! Besides, anyone who has the Cookie Monster for an avatar can't be all bad! HA!

What HappyFeat said about seeking feedback on his outfits bears mentioning. If we don't get criticisms on the outfits we wear, be it positive or negative, how are we to know if we're progressing when it comes to fashion and presenting a proper public image, regardless of what we choose to wear? If I seem a bit fanatical when it comes to preparation, it's because I find it important to look my best while in public in the hope of getting feedback so I can learn right on the spot if I'm doing things right when it comes to piecing together outfits. Sadly, I've gotten very little feedback, but on those rare occasions when I have, it was positive, confirming that the hard work I put in before I head out the door does indeed bear fruit.

[kneehighs]

Just one more thing about preparation that exceeds in importance good personal style--is a good attitude towards oneself about wearing heels.

Guys need to detach from the need to get the approval of both men and women when they wear their heels. "How can I detach from getting their approval of my heels?" Detach from the outcome, yet expect the best from others.

You'll feel much more relaxed, much more at ease with yourself, and that will rub off on others.

[HappyFeat]

I couldn't agree with you more kneehighs! Though it is fun for me to gauge reactions, at some point I have just become too old to worry about what other people think. The plethora of threads in this forum about gaining approval tend to reiterate the same things and it just seems to stifel way too many people. The bottom line is, if you were heels, you are different. What people think is moot and only matters what you think. Where preparation comes in mind is I tend to choose the places I go when wearing heels quite carefully. In a way, I am engaging in my own form of stereotypes, but as a human animal it is what it is. For example, I may not wear heels in a rough neighborhood or to places that I am not familiar. This is just to avoid too much hassle. However, many guys here have gone places that I would have never dreamed of. For that matter I have gone places that I would have never dreamed of not too long ago. The more confidence I have, the better I carry myself, and the better I work whatever I wear. The only outcome that any heeler should worry about is whether that did as they pleased and if they pulled off the look they want.

[Bubba136]

The plethora of threads in this forum about gaining approval tend to reiterate the same things and it just seems to stifle way too many people. The bottom line is, if you were heels, you are different. What people think is moot and only matters what you think.....

This is complicated. The hesitancy to wear your heels in public where everyone can see you comes from fear of ridicule based on societies identification of certain types of clothing exclusively to specific sexes and general attitude toward anyone that crosses the gender line. Therefore, so much attention is paid by anyone willing to "crossing the barrier" without generating reaction -- good or bad and the feeling of euphoria after a successful outing wearing high heels..

[quot] The more confidence I have, the better I carry myself, and the better I work whatever I wear. The only outcome that any heeler should worry about is whether that did as they pleased and if they pulled off the look they want.