The Purpose For Preparation

[JeffB]

Back in the old days when all I wore were the shoes, in the beginning, it didn't much matter what I wore, I won't deny that. However, as I began integrating women's clothes into the equation, beginning with skirts, then tops, then hosiery, and finally dresses, it occurred to me early on that it was important for me to look my very best if I was going to wear women's clothes in public as a man, and that meant doing prep work before each and every outing I undertake.

Because of the incredible (some might say mindblowing) variety when it comes to women's clothes, it was crucial for me to take as much time as I needed to properly pair tops, skirts, hosiery, shoes, outerwear, even handbags in order to assemble just the right outfit for a jaunt. And I take that prep time SERIOUSLY as it's not uncommon for me to spend upwards of an hour or more putting together an outfit, taking into account the surroundings I'll be in for the day, plus the season and the weather on a given day, to that end, I have separate tops and skirts for both spring/summer and fall/winter. I take all those factors into consideration when I select what I wear, because appearance is EVERYTHING to me because I don't want to be seen as a freak show because I'm a man wearing women's clothes in public AS A MAN. And I'm not afraid to say I'm rather anal, if not obsessed with presenting the best possible image for my outings. If I don't like what I see in the mirror, I don't leave the house. Period. Full stop. End of story.

Some might think that makes prep time a bore. Far from it, that time is fun for me because I get to wear women's clothes which I absolutely LOVE. When I stare at myself in the mirror when garbed in a nice top, a sharp skirt and a pair of heels, I can't help but smile because of how good I look. On occasion, I lose track of time while trying on clothes, but I see that as time well spent since I'm working towards my goal of putting together an ensemble I like for an outing, and like I said, appearance is vital to me, especially when I'm accepted, even complimented for my public presentation by the populace. Here's something else when it comes to the topic of prep time, I often find myself thinking about the next outfit to wear while driving home from an outing I had been on, putting the wheels in motion in advance. Prep time is valuable to me, and for anyone who follows in my footsteps as a fashion freestyler, it should matter a lot to you as well.

[Mr. X]

Well said!  I agree with many of your sentiments.  My prep time as definitely increased over the years.  Like you, I started out with just the shoes.  But now I defenitely present more complete images when i go out.

[CAT]

Jeff, 

i agree with you 100 percent.  Even if you ask my girlfriend she will say when it comes to the clothes and the shoes I am "more of a chick then she is ".  The outfit needs to be well put together so you get a compliment and not a laugh.  She says she I get dressed I have a smile and a look on my face that only happens when I'm dressed up in a pair of heels and a skirt.  I tell her no that's not true but I will admit her that I know it is!!!  I think I look better in a skirt then a pair of men's dress pants. Just my opinion. 

[bluejay]

Well said JeffB. I too take a lot of prep time to plan what I'm going to wear out and if I don't like what I see in the mirror, I change it out. I want to look my very best too. I do get the compliments on my appearance, from the ladies and that encourages me even more to carefully plan what I going to wear out.

Happy Heeling,

bluejay

[MackyHeels]

Jeff i agree with you and completely understand. You say, 1 hour to get things prepared? If you have more to choose from may take longer as with me. Finally picking outfit that works sometimes is exhausting. Often with me i find i need to buy more only finding the other stuff is too boring or dated. Sometimes when i choose the right outfit i get bored of it after short few minutes wearing it. Usually that happens when i choose colours that are subtle understated. Before i was loud even clowness appearing wanting the obvious attention that my clothes made. Now i got to be little subtle yet feel restless in them feeling i'm invisible amongst everyone. 

[JeffB]

Thanks for the kind words, everyone! I'm glad, and gratified that there are so many like minded folks here regarding the topic of prep time which is important and can make the difference between being accepted for your appearance while in public, or being laughed at if you get it wrong.

Mr. X: Yes! It's all about the complete outfit from head to toe. And, as I said, I obsess over my appearance because i want to look my very best.

CAT: I've also said on a few occasions that I look better in women's clothes than men's, and I love how I can work a short skirt just as well as any female.

bluejay: Getting compliments on my appearance gives me a good feeling inside, making my hard work with prep time all the more worthwhile.

MackeyHeels: My ritual of sorts is to leave the house on my outings around ten a.m., so I usually start prepping around nine, sometimes sooner.

[purrkitty408]

Yes, just absolutely yes! 

While I do bendy dress at times, I also mix in Latex as well. The key to wearing anything "out of the norm" is to be clean cut, well put together, and most of all: confident!

In my opinion, shaving body hair from legs, feet, back, and chest are simply required for making typically feminine clothes look good, not just to me, but to those around me. I consider it a duty to break down barriers and stereotypes, and I think this is one of the best ways to do it: making it look good! 

 

Thanks for the post! 

Edited February 23, 2017 by purrkitty408

[Thighbootguy]

Going out fashionably attired is something I'm going to have to put more effort into.  I haven't worn anything (except a pair of sweat socks) from the guys side of the store for years.  I now have very few reservations about going out in a skirt or a dress.  I'm still struggling to understand why there are some days when the desire to dress in a skirt or dress is almost overwhelming and other days the desire is not there at all, but that is a whole different topic.  Unlike @JeffBand @CAT, whom I suspect dress for an outing, my dressing is for normal daily wear.  If I'm just going out to get the mail, or a quick run to the grocery, I don't spend a lot of time coordinating an outfit.  I usually notice what the temperature is going to be and then pick a pair of boots based on whether I'm wearing leggings/hose or jeans.  Finally I add a top and jacket, again, depending on the weather.  Of recent I have started to pay more attention to colors.  I used to wear mostly black but have discovered that I can (and enjoy) wearing colors and this complicates things a bit.  When I'm serious about going out, I will add some makeup and my favorite, false eye lashes, and jewelry.  This takes a time commitment, and I figure if I'm going to spend that much time, I ought to put more effort into the outfit.

I am still torn between JeffB's more reserved look with longer skirts and shorter boots and CAT's mini skirt and thigh boots.  I am currently in between with skirts/dresses either just above or below the knee and OTK faux suede boots with 2-4" block heels or the same boots with jeans.  When I'm at a musical venue it's with boots and jeans for a couple of reasons. First, most of the guys are fashionably attired in flannel shirts, jeans, and pony tails, and second, playing a guitar or cello while sitting in a skirt just isn't practical (but the boots look good holding the cello ). 

I do pay attention to outfits JeffB, CAT and others show us and try to learn from their example and for that I offer a heart felt thank you.

[JeffB]

TBG: You are quite right, I do dress mainly for specific outings as I can't wear women's clothes daily like you do. But, I'm fine with that as it makes my outings all the more special to me, thus my driving desire to prep like crazy before I head out in public. As for my "reserved" look, yeah, that suits me best, given my obsession for blending in with my surroundings, but, I do go a little wild and crazy at times with the miniskirts and thigh boots, otherwise, I love being a plain guy, or as plain as a guy can get when strutting about in a skirt and heels! Heh!