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Getting (Some Of) My Boldness Back


Lime15

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As I said in my introduction, these days I'm not an every day heel wearer but do wear them three or four days a week on average. To be honest I like "men's" sneakers and high tops just as much and I often joke that my sneakers are way louder in style and design than any heels I wear. After buying and purging heavily over the past few years, I last year decided that was enough and I no longer purge. I may sell, I may donate, but that has everything to do with having shoes I never wear or that I become less attached to over time. And hey, that means more money and space to buy more new shoes! It's a very happy cycle. I heel almost exclusively at home and my girlfriend is very supportive after that week or so of finding it a little strange. I'm really glad I let her know but I think she'd assumed such as over the years we've been together I've given her about 200 pairs of assorted heels. Now she has the big closet and I have the small closet. A couple years before all this I would wear heels out from time to time, no big deal, rarely had anyone even notice. Usual men's business casual and a pair of mid heel pumps. To make an even longer story reasonably shorter, I had a really bad experience one evening. I don't want to go into detail but it really shook me up. I'm not the type to back down or have anyone push me around but it just really got to me. Looking back I'm surprised I didn't swear off wearing heels outright. Well the desire never quite went away, and my chronic ankle and knee pain sure as heck seemed to be screaming for me to heel again. That lead me to getting back into heels for myself, getting more comfortable, eventually telling my girlfriend, and getting to the point now where everything is great in the world of heeling at home. However the desire to heel outside has come back little by little. It's not always practical for me as I'm often hiking all over the city on foot, but there are times when I would like to go out. I've taken some small steps, wearing oxfords and the like during the early morning hours in relatively quiet areas but in the immediate area I really don't think it would be a wise option. I'm all for wearing what you want but in the lines of work my girlfriend and myself are employed with, it would be really dangerous to run into co-workers or those we serve. What does all this have to do with this post? Occasionally in the summer, when the heat wave week would roll in, I would wear a skirt if I was at home. I haven't done this for awhile but it was always really comfortable. I had ordered a specific skirt from Torrid, among other things, for my girlfriend and really liked it when it arrived. So much that I ended up ordering another one for myself which arrived yesterday. I figured she's cool with me wearing heels at home (and shopping for them, that's never been an issue and now extends to shopping for myself), wearing pantyhose every day I wear any kind of pants, and has seen me in one of her skirts a few times (that can be a really fun night if in the right mood), then why can't I go back to wearing skirts at home in the summer? So you say Lime15, you're going to wear a skirt and heels at home, big deal. Well this is where things change a bit. I work from home on the side as a consultant, one of many side jobs I have. Everything is done from home and we have video teleconferences twice a month in the current arrangement. So I figured, I'm at home, the people I'm working with have known me for a long time, and there are severe confidentiality agreements in place... I'll use this as a confidence booster. So for this morning's conference I skirted up, as I like to say, and wore my La Femme platform pumps along with some nude pantyhose. I figured wearing one of my usual dress shirts would be a cop out so I borrowed a top from my girlfriend's wardrobe. I thought I looked pretty good, still myself, and very comfortable amid the humid conditions today. The camera usually catches you from the waist up at best but during the conference there were a few times when I had to roll my chair back to grab some notes and my entire outfit was visible. The meeting didn't miss a beat although after it wrapped and a few of us were talking as people were disconnecting, I did get asked what I was wearing. My response: "Do you know how hot is in here?" When asked about the shirt I replied that they hired me to improve their corporate image, I can't very well appear to them with some drab collared shirt that doesn't match my skirt. The whole thing was a pretty big confidence boost and we talked a little more about men wearing heels, equality, social taboos, it was great. I can't say it's going to make me instantly want to heel publicly again in any "real" capacity but it did make me hold my head up high and something to think about when I get a little shaky again looking at heels in a retail store or the like. I've attached a few pictures of the outfit in question. Unfortunately I did have to do some cropping for privacy concerns - I really can't put the "regular" job at risk right now.

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Well, bravo to you, Lime! The outfit you sported in those pictures certainly did look nice, and the boldness you displayed was another plus in my book. I would agree that it's better to take things in steps instead of jumping into the deep end of the pool right off the bat, so you're doing it the right way. Keep up the good work!

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

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I like the color-block skirt, but something doesn't seem quite right with that outfit but I can't put my finger on it. Something just looks out of balance and I'm not sure why. It could just be the camera angle. I know what it is, No BLING! I think JeffB would agree with me on that. The whole outfit is begging for something dangling around your neck. Check out JeffB's stuff and you'll see what I mean. Other than that I think you've done rather well Lime

Shafted, the boots that is! View my gallery here http://www.hhplace.o...afteds-gallery/ or view my heeling thread here http://www.hhplace.org/topic/3850-new-pair-of-boots-starts-me-serious-street-heeling/ - Pm me if you want fashion advice or just need someone to talk to.

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Thank you JeffB, wedgemao, ShockQueen, and Shafted.

I like the color-block skirt, but something doesn't seem quite right with that outfit but I can't put my finger on it. Something just looks out of balance and I'm not sure why. It could just be the camera angle.

I know what it is, No BLING!

I think JeffB would agree with me on that. The whole outfit is begging for something dangling around your neck.

Check out JeffB's stuff and you'll see what I mean.

Other than that I think you've done rather well Lime

I rarely wear any jewelry other than the promise ring my girlfriend gave me (another long story but after being friends for six years we bought each other rings on the third day we were dating and that was almost six years ago) and a nice wristwatch, which I had removed prior to taking the pictures. Years of electrical and mechanical repair scared me away from wearing any real jewelry but maybe that's something else I can look into. Thanks again all!

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You're gonna chuckle. I think a necktie in the same blue as the skirt would look good as would a complimentary color like yellow. No clip ons.

Shafted, the boots that is! View my gallery here http://www.hhplace.o...afteds-gallery/ or view my heeling thread here http://www.hhplace.org/topic/3850-new-pair-of-boots-starts-me-serious-street-heeling/ - Pm me if you want fashion advice or just need someone to talk to.

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I like the color-block skirt, but something doesn't seem quite right with that outfit but I can't put my finger on it. Something just looks out of balance and I'm not sure why. It could just be the camera angle.

I know what it is, No BLING!

I think JeffB would agree with me on that. The whole outfit is begging for something dangling around your neck.

Check out JeffB's stuff and you'll see what I mean.

Other than that I think you've done rather well Lime

Hmm! After reading Shafted's comments (Wow! I was shocked that Shafted suggested bling! HA!), I've looked over the pics again, and yeah, a neckchain or pendant would provide some nice contrast against the dark color of your top, Lime. Nothing overly flashy like what gangsta rappers wear, rather something nice and subtle and tasteful. Give it some consideration. That could well work for you.

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

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You're gonna chuckle. I think a necktie in the same blue as the skirt would look good as would a complimentary color like yellow. No clip ons.

I usually wear neckties and collared shirts as part of my business attire but wanted to try something different this time. I think you're right though, a matching necktie would work well. Something to try in the future!

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  • 2 weeks later...

I've attached a few pictures of the outfit in question. Unfortunately I did have to do some cropping for privacy concerns - I really can't put the "regular" job at risk right now.

Nice outfit,I especially like the top,it suits you well.
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  • 2 weeks later...

Thank you all for the recent comments! Well I've decided to return to an old job and return to some form of steady income. I really enjoy being a freelancer, as well as my other half dozen side jobs, but I also really miss having a guaranteed income baseline every week. The new (old) job is a no heels job (slacks and sneakers but I can't really complain) and with it I'm going to have to limit the amount of extra work I can take on but I've made a command decision of sorts. Especially now that it has begun to really warm up, on the days I work from home, or in part from home, I've decided to keep up with the heels and skirts - essentially whatever feels comfortable day to day. I'm not one of those people that slob around and if there's a conference call or a package to sign for, toss myself together to look like I'm working. When I work from home I get up early, dress casual but business appropriate, that's that. As I said before, it's about building confidence and comfort back up for myself, allowing me to be me. I kicked (haha) things off today by wearing my Torrid python skirt, brown collared dress shirt, and Payless Janine black patent pumps. It's been a great day thus far, got a lot of work done, signed for a couple UPS packages (incident free, no surprise), just a very comfortable day. I'm guessing the more I think of ensembles like this as just part of my work attire, the more comfortable and confident I'll become.

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Didn't notice this thread until now, but both outfits are very nice Lime. Good for you for wearing what you want, when you want, and getting more comfortable doing so.

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Thank you all for the recent comments!

Well I've decided to return to an old job and return to some form of steady income. I really enjoy being a freelancer, as well as my other half dozen side jobs, but I also really miss having a guaranteed income baseline every week. The new (old) job is a no heels job (slacks and sneakers but I can't really complain) and with it I'm going to have to limit the amount of extra work I can take on but I've made a command decision of sorts.

Especially now that it has begun to really warm up, on the days I work from home, or in part from home, I've decided to keep up with the heels and skirts - essentially whatever feels comfortable day to day. I'm not one of those people that slob around and if there's a conference call or a package to sign for, toss myself together to look like I'm working. When I work from home I get up early, dress casual but business appropriate, that's that. As I said before, it's about building confidence and comfort back up for myself, allowing me to be me.

I kicked (haha) things off today by wearing my Torrid python skirt, brown collared dress shirt, and Payless Janine black patent pumps. It's been a great day thus far, got a lot of work done, signed for a couple UPS packages (incident free, no surprise), just a very comfortable day. I'm guessing the more I think of ensembles like this as just part of my work attire, the more comfortable and confident I'll become.

I love the skirt :pulsingheart: it's gorgeous. I'm getting my work colleagues used to seeing me in a kilt, then I'll just wear a pencil skirt on dress down Fridays ;-)
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I'm getting my work colleagues used to seeing me in a kilt, then I'll just wear a pencil skirt on dress down Fridays ;-)

Seems like a good idea. Are they used to seeing you in heels too?

I could walk on sunshine, but I chose heels instead.

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Seems like a good idea. Are they used to seeing you in heels too?

Not yet, though I wore some black boots with a heel on with a plain black kilt yesterday ;-) People thought it was just a pleated skirt, so the next step is a pencil skirt of similar length :rocker:
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  • 5 weeks later...

Thank you everyone for your comments, they really mean a lot to me. The "regular" job has been eating up much of my time but I've been keeping up on my business casual with skirts ensemble on the couple (or one) days a week I work from home. Today my girlfriend lent me one of her skirts and a belt to go with it. Our skirt size is about the same although I'm usually down one since, well, I don't have curvy womanly hips like she does. Not as nice as having the same shoe size but heck, I'll take what I can get. I paired it with a black collared shirt, black sheer hosiery, and my Payless Janine pumps in black patent. This whole outfit has been EXTREMELY comfortable throughout the morning. Really makes me look forward to working from home next on Friday.

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