Skirting the Envelope

[scrappycoco]

Well here is my outfit for the day. I normally wouldn't wear heels with this skirt but I have been trying to find one of my pair of heels that would look good with this skirt. I know there are people here that wont like the mens shirt with the skirt, but I am just not comfortable in all women's clothing plus I don't think this looks too bad. Just figured I would pop up a picture and see what everyone's thought's where about how the shoe's look with everything. The outfit is a Browns polo shirt, with a just below the knee kaki skirt, nude hose, black LEI Mary Janes and a black belt. Let me know what everyone thinks.

[docs41]

Are you a long-suffering Browns fan? I used to be until Modell moved them out of Cleveland. Now I don't follow any sports because I realized that they don't really care about the fans. It's just a business--a really big business! You have my condolences. Your mj's are pretty cool...

[Pumps]

Well here is my outfit for the day. I normally wouldn't wear heels with this skirt but I have been trying to find one of my pair of heels that would look good with this skirt. I know there are people here that wont like the mens shirt with the skirt, but I am just not comfortable in all women's clothing plus I don't think this looks too bad. Just figured I would pop up a picture and see what everyone's thought's where about how the shoe's look with everything. The outfit is a Browns polo shirt, with a just below the knee kaki skirt, nude hose, black LEI Mary Janes and a black belt. Let me know what everyone thinks.

I'm all for mixing and I think it looks good.

[LovesHiHeels]

Well here is my outfit for the day. I normally wouldn't wear heels with this skirt but I have been trying to find one of my pair of heels that would look good with this skirt. I know there are people here that wont like the mens shirt with the skirt, but I am just not comfortable in all women's clothing plus I don't think this looks too bad. Just figured I would pop up a picture and see what everyone's thought's where about how the shoe's look with everything. The outfit is a Browns polo shirt, with a just below the knee kaki skirt, nude hose, black LEI Mary Janes and a black belt. Let me know what everyone thinks.

Your skirt and heels go well together but the whole look is ruined by the brown top. I have a number of skirts posted in the galleries part of this website and the look seems to work well with the black polo neck top I,m wearing.

[yozz]

I think it looks fine. This idea of not mixing sounds rather silly to me. Anyway, I one bought sweaters which they were selling both in the men department and the women department (and I bought from both in different colors), so how does that count? And tastes differ. What looks good to one may not look good to another. Sometimes I see women in outfits where I think: "how can they possibly do that?", even though it is clear that they are happy with it themselves. This last thing is what counts. If you are happy with it, it gives you the feeling of confidence, and that make you radiate `you'. If you do not want to radiate `woman', and you wear those shoes, I would definitely not wear a sweater that is very feminine, independent from what side of the store it comes. Y.

[skirtedvik]

Well here is my outfit for the day. I normally wouldn't wear heels with this skirt but I have been trying to find one of my pair of heels that would look good with this skirt. I know there are people here that wont like the mens shirt with the skirt, but I am just not comfortable in all women's clothing plus I don't think this looks too bad. Just figured I would pop up a picture and see what everyone's thought's where about how the shoe's look with everything. The outfit is a Browns polo shirt, with a just below the knee kaki skirt, nude hose, black LEI Mary Janes and a black belt. Let me know what everyone thinks.

You have matched colours well.

[JeffB]

Well here is my outfit for the day. I normally wouldn't wear heels with this skirt but I have been trying to find one of my pair of heels that would look good with this skirt. I know there are people here that wont like the mens shirt with the skirt, but I am just not comfortable in all women's clothing plus I don't think this looks too bad. Just figured I would pop up a picture and see what everyone's thought's where about how the shoe's look with everything. The outfit is a Browns polo shirt, with a just below the knee kaki skirt, nude hose, black LEI Mary Janes and a black belt. Let me know what everyone thinks.

While I mainly prefer solid colors for my tops, what you wore matched well with your skirt. Say, did you wear a t-shirt with that ensemble? This is just me, but I would've ditched that in exchange for a neckchain. Again, that's just me. Bravo to you and your outfit.

[lorriette]

hi scrappycoco, I think the skirt and heels go well, but a plain "t" or blouse with a light jacket would complete a good look. Think professional mum and 30 something, mmm just right.

[evoviii]

Being relatively new to wearing, I have been content for private wear of whatever male bottom with bare legs & heels. To me its about the experience and thrill of heeling, to experience what the lady "gets". I honestly had been concerned that it would propagate in some direction, and figured it would be the addition of a skirt to the experience. I've always liked the skirt/heel combination, and finally made up my mind to have a go at it. I have a few skirts available to me, some black and rust/brown colors; above and below the knee. My favorite is the black I guess, and to me skirting in bare legs isn't part of the experience, so it was easy to get some black thigh high nylon stockings. So far the experience is more agreeable than I would have thought. For some reason I have a take on the skirts with the 6"or so slit, and again I feel like I am at square one on something I know little about. And a measure of shame for trying something like this and letting it grow. For tops most male ware doesn't do to much for the experience, and I find myself looking towards lady-ware to fill the need. I have access to a few ladies sweaters, one a dark rust color with a wide flimsy turtleneck that goes well with the skirts I have; and the shame that I'm letting it expand to wearing tops. And the sweater goes well with some belts I have access to, stacking belts with each other, a wide with a skinny and a not so skinny. And there's the shame associated with that despite the fact I like it. I top it off with a ladies gold bracelet watch or three, or some slender leather strap watches. On the third "attempt" I could actually look at myself in the mirror briefly, and wasn't too horrified. I just hope I can hold the experience at this level, and not add bra's & breasts to the tops. I think I can keep it Warmer weather will probably bring the want for some sort of blouses, I don't know what I have access to for that. My waist is slim but my shoulders are wide. I can already feel my arms/shoulders stretching the sweaters somewhat. I don't want to go find myself buying women's clothes, tho I would like to get a couple skinny belts.

[Bubba136]

It's too bad that HappyFeat isn't as active as he used to be. Of all of our members, he has, perhaps, the best sense of clothing coordination of of us all. For our newer members, they might want to scroll back through the archives and review some of the outfits he's assembled and read his thoughts on how to wear what with what........

[bluejay]

Speaking of HappyFeet it has been a long time (months) since we last heard from him! Since he got married we don't ever hear from him. Bubba, you are right on when you said that HappyFeet could really put outfits together. Happy Heeling, bluejay

[tallguyinheels]

OK, those of you wanting to see my skirts with boots.... I've just picked up some new boots: Pleaser Flair platform boots. These might quickly become my favorites. I like the looks, primarily because these make my feet look small. The length of the shoe from back of the heel to the tip of the toe (in a size 15) is just 9 inches. The heel height is 5 inches exactly. In contrast, my avatar Pleaser Seduce 460 "booties" are 10-1/4" inches long wth the same heel height - but no platform. They are even about a 1/4 inch shorter than my Domina 6" heels. Both the Seduce and Domina have more pointed toe box. This is because the toe is very rounded. This is my first platform (except for an extreme 3" platform shoe I tried mostly for fun) and the last and heel are made in one piece of injected molded plastic. probably why they are fairly reasonably priced. We will see how the hold up. Went to the mall today in the long charcoal skirt and plum plaid skirt today. Made a complete loop and entered many stores - trying on a few skirts - looking for a more "spring" look - I'll probably go back and pick up a long khaki shirt from Burlington Coat Factory - that fit OK in a size 12 - $17 - but it is not lined. Anyway, I've tried a few different skirts on with the boots - short ones and long ones. The two short skirts are from Target (charcoal) and Gap (plaid - a little shorter) The Gap skirt I really like and the one I've worn shopping before. I also turned the tops of the boots down for a comparison in the gap skirt. The forest green skirt I really like - it is completely not wrinkle able - pull it out of your bag - put it on. The other skirt was on of my recent purchases from the Mall of America in Minneapolis - and the one I wore out and about today. The sales staff in the stores I visited today in the mall today were not as engaging as is other stores. politely helpful - however . And never judgmental. One store - the sales girl showed me three skirts - before she noticed I was wearing one myself - and only after me holding a kind of frilly khaki skirt up to me and "checking" the length. I guess that is either a compliment to my confidence, or perhaps how "normally" I handle myself, or to perhaps the pure unexpectedness of my appearance.

[JeffB]

Well done, tallguyinheels! Well done! Those new boots look absolutely fabulous on you, especially with the short skirt! You certainly do show a most unique style in the fashions you wear! Color me suitably impressed!

[crotchhiguy]

excellent combination of skirts and boots........you're looking good!!!!!!!

[Thighbootguy]

I echo JeffB's complements but to my surprise I find that I like the boots with the longer skirt. I feel I’d be remiss if I didn’t suggest that if you are enjoying wearing taller boots, go ahead and get a pair if thigh boots. They really will go well with the shorter skirts.

[bluejay]

Well done tallguyinheels! You look great in all the pictures posted! You have a great sense of style and color matching is fantastic. I also like your choice of boots. I have only gone out in a skirt a couple of times. I have a leather one that goes to the top of my knee. I bought a black skirt that goes to just below my knee, but I have not worn it out in public yet. But with the encouraging pictures of you in your skirts, I will be doing the same soon. Incidentally, You posted that you shop at the " Mall Of America" in Minneapolis. I was there in late August this past summer. I took the train from the Downtown area to the mall. I did find some great shoe buys there especially at Nordsrom's Rack. I bought 3 pair of heels there for really clearance prices! Some where on the thread "Who has bought some new shoes" I have a post on that shopping trip to the "Mall of America" Happy Heeling, bluejay

[tallguyinheels]

Thx for the positive comments all... TBG. Yes, though I've dabbled in the short skirts - the longer - below the need skirts are ones I feel most comfortable with. The ones I'm able to exit my car and enter a convenience store with little trepidation, for example. I'm not saying the shorter skirts are are not fun, and maybe, I'll grow as comfortable in those as I am in my boots, after all I've been "skirting the envelope" for what, the last three years? Bluejay, All I can say is, "find a look you like - something you look in the mirror and say, "that's me.", then go for it" And if the writing of my experiences, like those of Happyfeat, TBG, JeffB (and all you others) provide you a tad bit of encouragement or support - all I can say is "pay it forward!"

[tallguyinheels]

Out and about today at lunch in the Gap mini pictured above, and a light blue long sleeve dress skirt - and the new Flair Boots. It's a beautiful day here in ATL - 60's, sunny and clear. - first nice day in a while. A perfect day for a miniskirt excursion. First stop was a consignment store I had heard about - supposedly carrying good stuff... This time I popped out of my car with no trepidation, walked acrross the parking lot and started to sort through a rack of bottoms outside the store marked 75% off. I pulled a couple skirts that might fit and looked interesting and wandered inside. As I entered I held the door open for a customer (someone dropping off stuff I think. I got a smile and a thank you - a couple of more skirts on the rack - all were too small. - by just a bit. Chatted with the sales staff that offered that they were about to turn their stock and bring out spring fashions - and that I should be sure to stop in next week. There is a Goodwill nearby - so I'm off. The parking lot is busy - lot's of old folks wandering in and out. So I take a moment - hop out of the car. Straighten my skirt. (how many guys get to do that regularly?) Throw my purse over my shoulder and walk right in. Lot of looks, no comments at all! The place is busy and I locate and head for the skirts section. (it's not I Goodwill I frequent) I find a few I'd like to try - two of the - and Old Nave dark blue denim mini has a possibility ---- But it's really short. See the picture above where my fingertips are just past the hem? With this skirt, my fingers extend completely past the hem is probably 3 inches shorter. I have to think long and hard about wearing a skirt this short. No sitting allowed - even with tights! I think I might have purchased it anyway - except for a defect on the front right side. I finished lunch with a stop at a convenience store where they have seen me in skirts before - not one this short. I fill up my 55 oz Diet Dew. and get into check-out line as there's a couple of folks in front of me. It get a big double take from a businessman entering the place as I cue up for my turn. The clerk recognizes me and takes my $1.05 - but offers no comments - probably out of politeness, as the place is busy. For those of you seeking courage - take heart that, at least in my part of the world, no one seams to really care what I wear. Of the 30 or so people that saw in the hour of lunch, most are indifferent, and those I needed to deal with were polite and courteous - from the Goodwill "Changing room Monitor" to the staff at the consignment store.

[JeffB]

Tallguyinheels: Bravo to you! I certainly enjoyed your most recent outings as you've shown both style and boldness, and that has impressed me greatly. You've demonstrated the best way to go about your business in a skirt, simply act like it's no big deal, and, to be perfectly honest, it's not! Good for you, my friend!

[tallguyinheels]

another day, another day in a skirt - three days at lunch now. Today I visited a TJ Max, Belk, Express, Macys, Kohls, & Talbots outlet - tried on a few skirts - spring stuff isn't in yet. Got a couple compliments on my boots, and at Macy, the sales lady in one department said "That outfit is really put together." I was wearing my new flair boots - as I said earlier I really like these and the little platform is not even noticeable, though the stiffer plastic last requires a shorter step - almost like a 6 inch heel. Hey, who wants to be in a rush anyway? OK, under the boots I tied a maroon (almost violet) tights on top of black tights. My forest green skirt - with the lops of the boots turned down my knees and a little above and a little below showed the color that picked out a color on my tight plaid Ralph Lauren dress shirt. Black purse and a 1 inch wide black belt rounded out the ensemble. I finish with a trip to my tailor that had finished tapering a red dress shirt I purchased at the Mall of America. For the first time we talked a bit - she is Asian - probable in her 40's - and she commented, "so you like to wear skirts..." "Yes for about 5 years now - though I've been wearing heels now for over ten years" She says, "Well everyone is able to express themselves as they like." Well," I add, "almost everyone feels that way I think. I rarely get any feedback negatively from anybody." we talked about the heels, and how at here old place there was a shoe repair store inside as well, and she knew about replacing heel tips and such. She said, that I genuinely "looked comfortable" in that outfit. Perhaps the best compliment I ever received.

[tallguyinheels]

It's about time to revive this thread.... I usually take a summer break from skirts b/c I I prefer the looks of tights on my legs with skirts - and frankly it's just too hot to wear tights here in Atlanta. Also, school is now is session and my shopping excursions are usually at lunch - for some reason I try to avoid forcing a mom to tell her little son or daughter that there are unusual people sometimes - and a 50 year old 6'5" guy in a mustache skirt and 5"heels usually requires an explaination. For the last two weeks it's kinda cooled off here, so I've been to Fall clothes shopping. Heels and skirt mostly, b/c when you walk into a Talbots, or other woman's clothing store - there is no doubt who I'm shopping for. I've spend many trips to Goodwill and other thrifts as well as the regular "mall" stores - just because I'm finding lots of clothes I'd like to wear and the thrift store keep my spending down quite a bit. My latest outfit revolves around a LBD i found at Salvation Army - a size 16 that I've had my Tailor (see previous post) work on that I got back yesterday. As a guy I'm a size 10 or 12 from the waist down and a 16 or bigger on top. I've also picked up some knit tops and tights and a couple jackets. I'll try to get some decent pics up soon when I fine tune my presentation. The nicest thing about shopping, is I'm wearing clothes I think I look good in. The store managers are very accomodating - I ask permission about trying clothes on, and its easy to talk about improving one's style - that's the store personels job! Worst scenario was being askeed to try on clothes at the bathroom instead of the changing booths - coldwater creek (not going back. ) Jeff, and other Larger guys out there trying dresses here's some advice. Go for stretchy material, sweater dresses and such. If you are tall, a dress with a fitted waist will probably set too high. I've triesd successfully, turtle neck under shift dresses.- watch the arm hole size with some dresses - even stretchy ones and they are made for a man with a somewhat athletic build. Be back soon.

[JeffB]

Jeff, and other Larger guys out there trying dresses here's some advice. Go for stretchy material, sweater dresses and such. If you are tall, a dress with a fitted waist will probably set too high. I've triesd successfully, turtle neck under shift dresses.- watch the arm hole size with some dresses - even stretchy ones and they are made for a man with a somewhat athletic build. Be back soon.

I agree with your assessment. Sweater dresses are certainly the best bet, especially in terms of style and sleekness, and they can be accessorized quite well with belts and such. I plan to give one a try myself soon. Should be interesting.