Skirting the Envelope

[GTMHP]

Very nice!! GTMHP

[tallguyinheels]

Haven't posted much lately... I've worn the long and short Denim skirt and the off white Belk long chino skirt here a bit this summer. More often, I'm in long trousers and the Oxfords. Kudo's to JeFf and TBG - I just haven't the courage to go with a comfy short skirt. But with fall rapidly approaching I see my skirt wearing accelerating.

[roniheels]

Looks very comfortable and stylish for the Fall.

[JeffB]

Haven't posted much lately... I've worn the long and short Denim skirt and the off white Belk long chino skirt here a bit this summer. More often, I'm in long trousers and the Oxfords. Kudo's to JeFf and TBG - I just haven't the courage to go with a comfy short skirt.

But with fall rapidly approaching I see my skirt wearing accelerating.

Well, it sure takes a certain mindset to wear a short skirt, but it can be great fun, especially during the summer. But hey, long skirts can be fun too. I'm also eager for Fall so I can wear mine!

[tallguyinheels]

I've also - more than often - picked my standard Italian loafers to wear with the skirts. No heels. But just a relaxed look. Trouble with heels is I can't really find a tweener heel or Mary Jane or ?? in my size 15.

[JeffB]

I've also - more than often - picked my standard Italian loafers to wear with the skirts. No heels. But just a relaxed look. Trouble with heels is I can't really find a tweener heel or Mary Jane or ?? in my size 15.

Well, just keep on looking. On the Internet, there's bound to be a resource where you can find what you seek. For whatever it's worth, when I first started wearing skirts, I also wanted to sport a neutral sort of shoe like a loafer, but as I built up my confidence, I just said "screw it!" and began wearing heels with them. And I haven't looked back, though I'll break out the loafers ever now and then.

[Thighbootguy]

tallguyinheels -

The long skirt is a very nice look, heels or no. Congratulations, by the way, on the fit at the waist. The inward curve of the skirt doesn't stop at the top of the skirt. I'm still working on that.

[tallguyinheels]

TBG... Losing weight is a big commitment... I'm down 30lbs. with 15 more to go (at least) in about a year and a half. Wearing skirts was the motivator, wearing a waist cincher - actually two at a time - is a two edged blade for cutting weight - They drop your waist one size just putting them on - and while wearing them you are constantly reminded by the feel that you might not wish to eat so much! When I go out at lunch in a skirt, I'll often go to the grocery store and make up a salad - or sometimes just carrots and celery - another tad of feminization, I guess.... I've gone from size 14/16 to size 10 in a cincher - size 12 without!

[tallguyinheels]

Can't believe it's been almost a year since I've added to this thread... Perhaps because I have been heeling more in pants than skirts. I'm feeling a little more relaxed now, though, and I've done a little skirt shopping lately. Surfing www I came across this nice long skirt (my preference) "Ellen" from "not your Daughters jeans" and it's available from Nordstrom So yesterday I go down to the mall (in long pants and my avatar shoes) and wander for a brief while until a young sales women asks if I could use some help. I explain I occasionally wear skirts and was interested the the NYDJ skirt. She directs me to the rack and asks what size. I respond - probably 14 - but I'd like to try it on, and the dressing rooms are right near by, but I said I would like to be polite and if she would be uncomfortable with me in the "women's" dressing room I would go to the men's area to try on. She immediately said, "No, go ahead, here, these are anybody's dressing room, and she walks me in." "Nordstrom has great dressing rooms, BTW. I try on the 14 and the material is very lightweight and stretchy, and I can pull the waist 5 to six inched away from my belly. The sales lady comes back to check on me, "how does it look?" So I open the door, and give her a "Well what do you think?" I think at first she took in all in, the skirt and the heels (not sure if she had noticed before - eye contact and my being tall could have distracted.) Immediately, a little smile of surprise, perhaps, and she says that looks really nice. Genuinely, I think. As I thought similarly, though I was concerned with the size. So I asked, if she would get a size 12. The 12 was a bit tighter on the hips and showed my tucked in shirt lines. More of a problem because of the lightweight material - than the fit. My "assistant" agreed the 14 looked better, but I asked if there was another skirt made of more substantial material - I knew NYDJ also offered a shorter denim skirt. She came back with the second one - Khaki cargo skirt - It's hem falls a bit above my knee - I'm short legged, for a guy 6'5" that is - and looked really good, even in the size 16 - though my trouser socks should be replaced by tights for a proper look. And she asked if I had some knee boots adding that would be a good alternative. $88 dollars for a nice skirt seems a bit high - and I need to try it on tomorrow - in size 14. The best thing is that my "assistant" seemed to go from (perhaps) skeptic to advocate (almost). Being courteous and professional on my part - certainly helped in this way.

[Thighbootguy]

Sounds like you had a grand time!

I like the shoes in your avatar but I agree with the sales clerk, "she asked if I had some knee boots adding that would be a good alternative." Your option of leggings with those shoes would also look nice. I'm assuming you meant black leggings with black trouser socks so there wouldn’t be a contrast break. Black leggings with knee boots of any dark color would also work well.

Thanks for sharing the adventure.

[HappyinHeels]

tallguyinheels, What an amazing experience you had! Thanks so much for sharing photos of the two skirts. I don't recall ever seeing the maxi denim skirt anywhere. It looks intriguing, I wonder what would look best...ankle boots, wedges, or pumps?? It looks like it could work for a lot of us if we choose our tops and shoes wisely. I have looked in Nordstrom's but am more familiar with Nordstrom Rack--the "Disneyland" of heel retailers! I do understand though that Nordstrom's enjoys a wonderful reputation with regard to guys and heels and women's clothing in general. HappyinHeels:wave:

[tallguyinheels]

thx for the positive comments TBG & HnH's I do like the look of the boots with the shorter skirt, but with legging or tights, I think you can pull of the "bootie" heeled oxfords. As you can see here. With the longer "Maxie" - just about ant shoe would work After leaving Nordstroms I noticed a Goodwill, just a short distance from the upscale mall - this is in a pretty nice area of ATL. I thought I check out the skirts... The Pencil skirt here was the first that was just the "right" look for the "professional" appearance I try to make in skirts. Also picked up a longer A line skirt "Talbots" branded - the longer one is 100% wool, 35" long and will be great this fall. For now the pencil skirt will be an adventure just 20 inches long but fits nice at the waist. Tried with a Belt - sorry just a bit long so it droops in front - and without. what do you think?

[wetwillie]

This is the first time I've seen this thread. Very interesting. I'm 6'2", 175lb. and I like to wear skirts too. I've never worn heels and a skirt at the same time. (in public) I've worn a kilt and heels together but with an actual skirt I've only worn my Birkenstock sandals. My wife doesn't approve of my skirt wearing in public but when she's away I've worn my favorite skirt, a denim cargo skirt, which could be considered a mini, about town with a tee shirt and men's sandals. I'm sure I've been noticed but no one has made any comments. I wish I had the confidence to wear my heels and a skirt at the same time. Maybe if I were far from home I might try it but in the small village where I live too many people know me, my wife, and my kids.

[tallguyinheels]

Wetwillie, Yes it is a little difficult if your spouse does not approve... I have the same consideration. Guys can compartmentalize - not a common trait for women. Enjoy the thread and have fun in heels and skirts. FYI, I'm in heels just about every day, I'm in skirts every now and then - my enjoyment vs. anxiousness level goes up and down. I don't want to wear a skirt and be anxious, I want to wear a skirt and enjoy how I look and feel. FYI feeling pretty good about the black pencil skirt look today.

[tallguyinheels]

To continue... I went out at noon back to Nordstrom’s in the pencil skirt/coral shirt outfit but switching in Black Seduce2000 5 inch heeled knee boots instead of the oxfords. About 6 inches between the tops of the boots and the bottom of the skirt – still using the “argyle” pattern tights. First to the dry cleaner for a pickup – another black skirt button up front mid-calf length – and they have seen me in skirts before – they are all business. Parking spot right in front for an easy in and out – I purposely did not use the drive through just to get the out of car jitters over. (There is a Subway “deli” right next door, however) Like I said – a minute or two, in and out two guys leaving Subway at the same time I leave but I don’t think they noticed. On to Nordstom’s. OK, admitting jitters getting out of the car but once out in the open, immediate relaxation. “Can’t do anything about what other people think.” The 200 ft walk to the store with other shopper coming and going was actually calming. Those that left the Nordstrom entrance either noticed and didn’t care, or didn’t notice at all. In the store I strode toward the center escalator, needing to go one floor up, and whether people noticed, or not, I didn’t care. It’s summer time here and while in my 5 minutes of anxiousness in the car, I was noticing the mostly women traffic in and out of the store’s doors were mostly casually dressed, and many down right frumpy. And I’m looking professional and polished, just a well dressed man in a skirt and heel. The match for any woman’s (or man’s) outfit that had already entered. On the second floor, I strolled back where the young sales assistant had helped me Monday. Not to be found, a 40ish, and can’t believe Nordstrom let’s her dress like that (slacks and a shirt, but both too tight – I first thought she was a customer) sales lady ask if I needed assistance. Tried on the same as before – but this lady was not accommodating – plus the place was a bit busier this afternoon – so there were other to assist. I passed on the khaki skirt, because it was not lined it did not hang as well as earlier b/c of the tights. Just too lightweight material. Message “Stay away from unlined stretchy material in a short skirt – when it’s likely you won’t go bare legged. I poked around Nordstrom’s a bit before leaving. “A shorter skirt perhaps?” and I think of TBG in his micro mini’s, almost laughing out loud in the process. And guess what? The down escalator was broken, you have to use the elevator or venture into the mall to decrement one level. I chose the latter. By now I’d tried on a couple of skirts and talked with the saleslady a couple of times . Btw, she also said she liked the long denim skirt best. Oh, and before leaving Nordstrom’s I got a full up and down disapproving look from a woman about my age, as I walked up and thanked the sales lady for her time. Not far up the mall I decided to enter the almost adjacent Bloomingdale's instead of taking the mall escalator down. More shopping! Asking for moderately priced skirts I was directed to an area where a younger Asian sales lady assisted me in finding a few skirts – a shorter than I was wearing black pencil skirt from JNY, and a similar one from Calvin Klein along with a denim Calvin Klein skirt about knee length. The CK Denim just didn’t hang right at all: Almost no waist and just didn’t fit well, The CK lined pencil was quite a bit shorter – almost mid calf – and the JNY was a bit in between with the JNY a bit tight, the dressing room was a bit warm – And I decided I had enough. But a good outing in my shortest new thrift store skirt

[Thighbootguy]

tallguyinheels – Again it sounds like a really great outing. Too bad you didn't get the same sales gal.

For what it's worth, I'm not a fan of pattern tights. I prefer a solid color, but that’s just my eye.

I'm glad you gave the Goodwill a try. The selection varies GREATLY from store to store and day to day. If you visit often, you can find some great stuff at cheep prices.

Thanks again for sharing your adventure.

[danielp6406]

tallguyinheels :-)

About your post # 69 on previous page.

Picture # 1: First time I see a maxi denim skirt as narrow as this one. Wow !

Is picture # 2 a side view of the same skirt or is-it a different skirt ?

It is unfortunate we don't have Nordstrom store here because I would try it for sure.

How this long skirt feels while walking ? Do you need to take smaller steps ?

BTW, nice thread. I never saw it before. It was good to read. Thanks for posting !

[tallguyinheels]

danielp... The two pictures are of the same skirt. The skirt is a light weight denim and it hangs fairly straight with a 15 inch or so slit in the back - The front shot makes it look a bit like a hobble skirt - which it certainly is not - though a little tailoring could easily convert it to such. I liked the long length. FYI- Not your daughters jeans are available from many department stores, and directly on the manufacture's website. $110 ouch! TBG - that's OK, I only like "manly" pattern tights when I wear my skirts! Argyle, Herringbone, Ribbed - No hearts, flowers, and any other frilly design. (Sorry if the humor doesn't come through the posting - Just laughing at myself.) Actually, this was my first pair of tights, and I went out shopping for a ribbed design, but in visiting 6 different stores at lunch Tuesday - Kohl's, Target, Sears, Belk, JCP, & Macy's - the hot weather here in Atlanta has seemed to minimize the availability of tights, and I came up empty - on ribbed - there was a good choice of frilly and plain designs, though. These came from Target.

[tallguyinheels]

OK, here is today's outfit. Deciding on the skirt - The new 27" pencil (this time with the boots) or the 33 inch button front A line skirt I mentioned a few post's back. I'm in a maroon T shirt this time - the skirt really dresses up the T in my opinion. I know it's more of a fall look - but fall is just a month away!

[JeffB]

tallguyinheels: Bravo to you and your recent outings! You've shown yourself to be bolder than I am for wearing your skirt and heels in a mall, something I've yet to do! And doing some shopping to boot! By the by, your outfits look pretty darn sharp if I do say so myself. I am certainly impressed with your sense of style in what you wear. Hope to read more of your exploits in the future.

[tallguyinheels]

I'm a bit embarrassed as I think you have been as strong a motivation for me to wear stylish skirt and heels in public as anyone here. As for shopping, it is a motivation to me to wear the skirt into a women's clothing area, and say to a sales professional (Honestly) "I'm a guy that occasionally, as you can see, likes to wear skirts in public, I always like to look professional, and I never dress or wear makeup to look feminine." That leads to a usually a positive experience. Friday, I weny to a mall in a more conservative area of ATL. There are some outlet stores for Neiman Marcus and Saks5th. Walked in with the outfit show last to NM first. (note on malls - I'm always more relaxed entering a store directly than a general entrance ). I'm kind of looking for a shorter skirt that would make TBG or JeffB proud! nothing there, but as I worked my way toward the mall entrance at least one small group (younger Asian) in the mall had looked through the store's mall entrance and noticed me shopping, gawking and even pointing. (OK, I'm sure I present an interesting image) I waited a bit before exiting into the mall, it is not my desire to perform! In the mall, I passed many individuals and groups and a few passed me. Looking into shop windows is what most people do, and I am like most people, I guess. Not one negative gaze or comment best I could tell. Saks5th was even worse than NM for skirts. I was in and out in less than 5 minutes. Headed toward a store called "Perfect Bodies", because mine is not! They specialize in compression garments for women and men. I admit to wear two "Flexees" waist cinchers (size small) when I wear skirts, a skirt just looks better worn when you have a waist! I was hoping they had a single thinner garment to duplicate the dual cinchers. The two sales ladies greeted me and I explain my situation (exactly as above - so much power in honesty), and they are eager to help me, but first both the ladies mention my boots and the tall heels and how I manage in them. "practice, I wear heels like this almost daily - and I can walk all day in them" Unfortunately, after a good 1/2 hour of trying different garments, men's and some frilly women's styles, nothing seemed to be better or more comfortable than my current solution. But keep in mind, I am 6'5 inches (195cm) tall and have a torso more like someone 6'8" (203cm) tall. On leaving, I was complemented on my appearance and again on how I handle the heels. I walked out feeling even taller, visited a couple of smaller shops, still unsuccessful in shopping - but a very successful outing in skirt and heels!

[danielp6406]

...I admit to wear two "Flexees" waist cinchers (size small) when I wear skirts, a skirt just looks better worn when you have a waist! I was hoping they had a single thinner garment to duplicate the dual cinchers...

I could not agree more with you. I also wear a waist cincher when I wear skinny jeans.

I recently discovered a single thinner garment which works great for me.

You may want to take a look at it here.

Not sure if it will be OK for you with since you are quite tall. Give it a try !

[JeffB]

tallguyinheels: Bravo on your latest outing! You certainly do exude plenty of moxie and confidence when you go out in public, and going into stores and asking salespeople for help with clothing purchases as well. I am most impressed with you, my friend, and you've given me ideas for what I'd like to do in the future.

[tallguyinheels]

JeffB: Good luck and good fortune to you. The other aspect of engaging others - sales associates, my hair dresser, dry cleaners and such - is that it a bit more "active" to the cause than the passive activity of wearing heels and skirts. Maybe, (At least I imagine) there's a conversation later between associates, girlfriends or a husband: "This guy came in to work today wearing a skirt and stiletto boots!" "Some kind or weirdo or something?" "No, he was 50's, polite and looked pretty nice" "What was he there for?" "He tried on some skirts - a long one where he looked alright, even with the heels!" "Some freak I would guess, You say he looked OK?" "Yes, in a nice men's T-shirt, Polo I think, Tan, somewhat fit. I really did a double take when I first saw him. He must have been 6'9" inches in those heels, He walked steady and it wasn't until I looked down did I see he was wearing an at the knee black pencil skirt, with knee boots!" .... Of course this is my optimistic view - don't think I could do this if I thought something else.

[skirtedvik]

You wear heels made for women on your male feet,you wear skirts made for women on your male legs,why don't try tops made for women on your male body.Works for me,just pick the right models,mate.A women's top will not look good on all women,same applied to men !

[loveheel]

Tallguyinheels: congratulations. I always wear heels when shopping in Nordstrom but haven't had the guts to do skirts. Like you I have had extremely good experience with the sales people. They always set me up in one of the "nice" dressing rooms in the high end area of the store. Very relaxed, and indeed nice dressing rooms ! I have stayed in hotel rooms that were smaller ! I have never had difficulties at Nordstrom. At worst I have had a sales person that was disinterested, but I just assume they are the same with everyone.

Today I went to my local Nordstrom here in Massachusetts with my GF. I was wearing linen pants with wedge heels, and my favorite Jimmy Choo handbag. First sales girls was OK but not helpful, so we just strolled along. Found someone who was enthusiast about helping me and my GF, so we tried on at least 15 things together. Ended up buying a Missoni skirt and a Vince sweater. My GF also tried on some Prada and Jimmy Choo pumps, but we passed on them. She looked gorgeous in them, but just too expensive. Here is a link to the pumps.

http://shop.nordstrom.com/s/jimmy-choo-cosmic-suede-platform-pump/3196356?origin=category&resultback=730

[tallguyinheels]

So, another shopping adventure. This time last Wednesday at the Loft. In mid afternoon, I stepped into a busy strip mall store (at least a half dozen customers) and walked up to the sales counter. This is a lot different than walking into Nordstrom at the same time of day, which required passing a the half dozen or so customers transiting the parking lot or passing them in the aisles heading to a nearly empty (and large) women’s clothing section. These women and I would share shopping space for a while, and I left no doubt what I was shopping for, as I was in my 27” pencil skirt, a button down Polo short sleeve shirt, a small handbag on my shoulder, and my 5 inch oxford heels at the end of my legs sheathed in argyle pattern tights. I can’t believe the freedom you feel once you commit to the task of wearing in a public situation. Relaxed at the sales counter, I explained my interest in a trying a skirt or two I noticed on their website. A tall mid 30’s, black (though not relevant to my “color blind” ethics) sales assistant – Lea directed toward one of the skirt styles, and asked my size. I said, “I’ve not yet purchased anything from the Loft, but my experience says anything from size 12 to 16 – Let’s start with a 14 – but I want to make sure it is OK to use the changing rooms – I don’t want to put the store in an awkward position with its other customers.” She said she appreciated my concern would ask the manager, whom acknowledged me and said essentially, “no problem at all.” Lea took me back, and led me to one of many changing rooms, and said she would be back to check on me. This skirt was about 22 inch long – just above the knees and the size 14 fit pretty good – it was made of what they called “scuba” material – and it has a bit of the feel of neoprene – even though it was a woven material. Very stretchy. Lea comes back and asks what I think, and I immediately open the door and asked her what she thought. She takes me all in, and her affirming smile – with a bit of surprise – expression certainly built up my confidence. We discussed the fit a bit and how the material looked good as it draped nice and straight, but maybe a little loose on the waist. She offered, “Why don’t you check what it looks like in the 3-way mirror at the far end of the changing room?” So I just strutted out of my booth and past several others (probably three other women in the changing room area along with a couple additional sales staff.) Now, I am the center of attention, relaxed and trying on clothes and checking to see what looks good on ME. One of the other sales assistants asks about my heels, “Are they from Nordstroms?” (“No, I have to buy my size from the internet.” “Size 15?”, she responds to my answer to her next obvious question, “ They don’t look nearly that big.” I affirmed, “Well that is one of the beautiful things about high stiletto heels.” Lea, suggests she has some others skirts I could try. She brings a grey size 12 in the same skirt and another “scuba” material skirt (grey and a dark maroon that has an interesting lace like overlay – it looked good – actually – it was also in a 12 – and was maybe an inch shorter. Each time I walked out the mirror, checked myself out – while enjoying all the attention. Lea went out for a moment and came back with a “Faux Fur Collar Sweater Coat” and said this might work. I had to catch her, and say, “You know I don’t ever dress as a female – only as a professional looking guy in a skirt – now and then.” I added that I wear the heels much more often – with slacks and jeans.” With that settled, we went back to skirts. While she was pressing the Lace “scuba skirt” (lace is too strong a word – it wasn’t “frilly” just a contrasting texture - I asked if there were other skirts there and she brought back this nice – little bit shorter – dark navy pin stripe maybe 21 inches long. Belt loops, zipper, tab closure (I’m still not efficient at hook and eye clasps). Tried it with the belt I came in with…. This turned out to be my favorite. All together I was in the Loft for about an hour, tried on 5 skirts types - some in multiple sizes. A couple skirts I repeatedly tried - switched back and forth - and thoroughly enjoyed myself. Note: Wore this ensemble on the way to work this morning, and I stop at my usual convenience store, where they see me once a week or so in a skirt, usually on Tuesdays. Often, I wait a moment or two to gather myself before going in. Today, I just went for it. The slightly chilly morning, felt good on my tighted legs as I hopped out of my truck. There is no doubt this is by far the shortest skirt I’ve ever worn in public. The length, from the hem the top of my hips, where slacks or jeans might rest, is just 15 inches… The visit was uneventful – For some reason the place was not that busy – I often have to wait 4 or 5 deep in a cue to pay. There was a scowl from a construction worker type capping his coffee, while I approached to fill my cup. I was greeted by the counter staff with no comment, and I got the prerequisite double take from a women dressed nicely – long skirt, white blouse, short jacket, wearing loafers - as I held the door open for her on my exit. Maybe a lunch-time adventure will yield more interest of comments. Note 2, unable to upload pictures... Anybody else having that problem?

[Thighbootguy]

It sounds like you had an absolutely wonderful time! Wow, and hour trying on skirts and having someone helping. I discovered (and it sounds like you have also) that the key to wearing anything, from a guys business suit to skirts and thigh boots, is wrapping your head around the idea that it looks good and believing that you like the look. I suspect that the failure to do this is one of the reasons more gals don't wear thigh boots. Once you're comfortable and confident with your image (a professional looking guy in a skirt) it's easy to "go for it". The "believing that you like the look" is the hard part, especially when you want to present a look that is non-traditional. This could be "guy in a skirt", guy or gal in goth, gal in a business suit with tie, guy or gal in stiletto heeled thigh boots,… If you present your image with confidence, most other folks are willing to let you give it a try. (I know, I'm preaching to the choir. ) Unfortunately I have to limit my shopping for my hobby to thrift stores where they often have fitting rooms but no sales assistants. A few times I have had a clerk (or other customer) recommend something for me and that is always fun but I haven't been able to try the recommendation on and ask "what do you think?". I also don't want to waste the time of someone in a standard retail outlet when there is no chance of a sale. Thanks for posting your delightful adventure, and have many more. TBG

[Steve63130]

...All together I was in the Loft for about an hour, tried on 5 skirts types - some in multiple sizes. A couple skirts I repeatedly tried - switched back and forth - and thoroughly enjoyed myself.

So what did you end up buying? You didn't say, and it kinda left us all hanging...please put some closure on your great adventure!

Steve

[HappyinHeels]

tallguyinheels,

Thanks so much for sharing your enjoyable outing and all the support you had during the outing. It reaffirms the beliefs of some whilst encouraging others towards the goal of someday knowing the joys of shopping for heels or whatever suits your taste. If anyone here likes Nordstroms, which does enjoy a good reputation among the heel-buying guy crowd, just wait until you discover Nordstrom Rack which I call the "Disneyland of shoe stores". They have more shoes per linear foot of shelf space than anyone else and sizes up to 13 and the styles are amazing. Even the most conservative of us will want to wear heels into a Nordstrom Rack to get yourself into the right frame of mind. Nordstrom and Nordstrom Rack don't have stores in every state which is a problem but they do in all the heavy hitters like CA,TX,NY,NJ,PA,FL,IL,MI and a few more. I have shopped Nordstrom Rack in Chicago and Phoenix and wore heels into both.

HappyinHeels:wavey: