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First Time Out In A Skirt


JeffB

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Well, folks, I've gone and done it----finally! Today, I ventured out in public for the very first time in a skirt! Below is the outfit I wore:

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Nothing extravagant since I was out an about at midday and didn't want to attract too much attention to myself: Polo shirt, denim skirt, sheer tan pantyhose (no way in hell I was going out with bare legs) and comfy two inch heeled women's loafers. I thought about bringing my handbag for the ride to carry my wallet, cell phone, car keys and house keys but opted for a fanny pack which I wore over my shoulder. Here's my itinerary:

1st Stop: Swung by an ATM for some cash. I parked about twenty feet away from the machine, it took a good five minutes to screw up my nerve to exit the car, but I did, walked up to the machine and did my business. No one saw me so it was cool, giving me some confidence.

2nd Stop: With the aforementioned confidence under my belt, I drove to a Borders bookstore in a strip mall in the western burbs. This time, it took longer to get up the nerve to leave the car, ten minutes this time, after taking several deep breaths, I left the car, casually walked the fifty or so feet to the main door and went inside the store. Acting casual, like I belonged there was key as I strolled through most of the store, I had my eye on buying some manga titles (Japanese comics) that I collect, but the latest volumes weren't in, so I settled for the new issue of Sports Illustrated. All told, I spent a good twenty-five minutes in the store, taking my time as I wandered the aisles, the store was fairly well populated, including teens and pre-teens, but no one gave me so much as a glance, never mind a double take at seeing a man in a skirt. After I left the store, I was feeling pretty damn good, thinking this was easy.

3rd Stop: Arby's for lunch. A skirted man has gotta eat. After parking in the lot, I just got out and walked in, no time spent mustering my courage because it was already there. At the counter, I ordered my food, paid for it then ate, not many people in the place, but again, no one gave me the time of day, despite how I was dressed. Again, I marveled at how easy it was. Afterward, I returned home to take the picture I enclosed with this post.

All told, I thought this first outing in a skirt was pretty successful. I was able to go into mainstream places and not garner any negative attention, hell, I didn't garner any attention at all, and a tiny part of me was almost disappointed. In any event, I can't wait for another chance to come around so I can indulge in a skirt outing. Guys, this is FUN!!

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

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Well done you are a braver man than me. All credit to you!

Yep, what he said. :smile:

I have in my mind the thought that skirts (just about any skirt) don't work on men. I have to say, if I saw you dressed as the image included, I'm not sure I would even notice. It just doesn't look odd.

The overall look, is, very wearable. :thumbsup:

Well done you! :thumbsup:

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Thats great JeffB! Nice outfit too. You´re a bit like me, about the pantyhose. I´m wearing pantyhose dayly to office if I´m wearing hig heel pumps, that is. If I´m wearing high heel sandals, well its no nylons for me then. See you was thinking of bring your handbag. Its good you have one. I guess you come to this conclution, just like me. When wearing a skirt you´re going to need a handbag. Me I´m never going out with out my handbag, weather I´m wearing skirt or not. Can´t be without my handbag. Its sort of has becomes a part of me now. I just need to have my hadbag with me where ever I go. GOOD LUCK!

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Thanks for your comments, everyone. I appreciate them. highestheels: Yeah, it took a hell of a lot of courage to leave my car and be seen by the world around me, especially when I was in that bookstore. But that made it all so exhilirating. It was so incredibly thrilling, being outside in a skirt and I enjoyed the experience greatly. fastfreddy2: I would agree than not every man can pull off wearing a skirt, even something as casual as denim. I sought to blend in with my surroundings instead of standing out, I wanted to look as normal as everyone else out and about, and I guessed I pulled it off as no one gave me so much as the time of day. maninkirt: Admittedly, I'm somewhat self-conscious when it comes to showing off my legs, which was why I wore pantyhose. In retrospect, I wish I had brought the handbag with me as using that fanny pack was a tad awkward. The next time I go out, I will use the handbag!

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

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JeffB Its good that you realized that you wished you had brought the handbag. A handbag is a must when wearing a skirt or a dress. As I said before me I´m always using a handbag weather I´m wearing a skirt, dress or jeans/pants. I can very easy found my things, my wallet, my keys, my cell phone. I also have a comb, a hairbrush, a litlte make up mirror and my make up things. A handcerchief, a pen, a note pad, a pair of extra pantyhose (you don´t know when you have to have an extra pair, I hate having runs on my pantyhose). This is the things I have in my handbag, for my everyday use. I guess you see thats why I can´t be without my handbag. I´m sure when start being out in a skirt more often you soon realize, yes you need a handbag, You can´t be without one. Its fun, its cool matching your handbag with the rest of your outfit, with different style and colours. I do all the time and I can asure you its great fun. I try matching thhe style and the colour of my handbags with my skirts, my heels, my outfit. Its great fun, try it, I´m sure you going to like it and yes I´m sure next time you go out you will use the handbag just like me. JeffB there is no other way to do it.

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I started reading your post Jeff and my first thought was "oh no another man in a skirt making us all look wierd" but seeing your pic I have to agree with all the comments made, it looks, well, right. You look like a guy wearing a skirt, and make it look like all men wear skirts and it's as natural as can be. Kudos to you for a) having the courage, and :smile: doing it with such style and making it look right.

He was so narrow minded he could see through a keyhole with both eyes.

Brown's Law: If the shoe fits, it's ugly

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Jeff – My goodness gracious, what a fine looking outfit. The denim skirt and loafers look great together. I would suggest a less busy shirt and raising the waist an inch or so but that’s just my liking of the proportion. Since you goal was “to blend in with my surroundings instead of standing out, I wanted to look as normal as everyone else out and about”, the denim skirt was a great choice. :smile: I was surprised when I read that you were having trouble getting the car door opened. I thought that wasn’t a problem any more (I know, the skirt got caught in the door.). :thumbsup: I had been looking for a word that describes what it is like wearing a skirt in public and hadn’t found one but you use of “exhilarating” hits the nail right on the head. I’m glad you enjoyed the experience. Now all you have to do is dust off that pair of boots you have and ……. :thumbsup:

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

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maninkirt: Yes, after my outing yesterday, I've come to realize the importance of having a handbag to keep my stuff in, even if it isn't all that much (wallet, car keys, house keys, cell phone). I certainly have it with me on my next outing. Just gotta figure out when that'll be! shyguy: Come now, if you're at all familiar with me, then you know I would never embarrass heel wearing men by looking weird. That's not how I roll. :smile: I'm glad you felt that I looked "right", in a skirt, it felt right to me after I got over my initial case of nerves. Guess that means I did something right. HA! TBG: I was eagerly awaiting your comments on my little outing since you were my inspiration after having read all your own remarkable adventures. By keeping a low profile in the outfit I sported, I was able to build my confidence, but that didn't stop me from enjoying myself. As for your advice, it's certainly sound, and I'll take it to heart for my next outing. Oh, yeah, I do have an idea in mind for pairing a skirt with my boots....

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

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Great posting, JeffB! You pulled it off flawlessly! I think that's the whole key right there - making the look become totally natural, and just being yourself. It shows that you are comfortable with who you are and what you wear. Once you cross that hurdle, everything else is just icing on the cake.

SQ.....still busting societal molds with a smile...and a 50-ton sledge!

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SQ: Thanks for the kind words! That first outing in a skirt was so exciting to me, but to the world at large, I had to act like it was no big deal, like I had done that sort of thing hundreds of times in the past. And yeah, it did feel very comfortable once I got over the initial nervousness, suddenly, I found myself wishing I had done this a lot sooner!

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

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I found myself wishing I had done this a lot sooner!

I think that has been said by more people on these boards than anything else. The hurdle gets cleared, and then......the realization. :-)

SQ.....still busting societal molds with a smile...and a 50-ton sledge!

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