SkirtDude

TBG's right, that length skirt would look great with thigh boots. But I know Booties are "in" now  Thanks for the Jaunt, though! A very bold look. I'd be freezing in that though !

Looking smashing of late, Jeff! Sadly, not seen any latest Jaunts... is everything okay  

1 hour ago, KneeBooted said:

I will need to acquire some sweaters or tops that better accent that. Truth be told though, I need to drop a few pounds, otherwise a shorter top would not only accent the top line of the skirt, it would accent my gut...

You are rocking that skirt! I love pencil skirts for the way they cling to my thighs. Naturally as a guy we don't sit well, but I learned how to sit in a skirt with this style and it just looks sophisticated and smart. I wear mine either at the knee or just above. Just bought a suede pencil skirt which I wear with boots, and in this weather, tights as well. I find panties more comfortable with tights as boxers tend to become very uncomfortable and ruin the contours of a skirt. I also wear denim pencil skirts as well, some with a generous slit at the rear to show off my legs in the summer! As regarding sweaters, turtle neck sweaters look great, and the tighter fitting sweaters suit a pencil skirt more than a baggy one

A great look! I bought booties like that and am experimenting with shorter skirts too! ♡♡♡ the belt too. Looking forward to what you will showcase next  

7 hours ago, JeffB said:

 

Well, I haven't misplaced my thigh boots, it's just been wet and snowy here of late, and my mantra when it comes to weather related outings, "If the streets ain't dry, then my heels ain't high" holds true. Not to worry, that first jaunt of 2017 will be on the way.

Even a pencil skirt and flats will do! I'm getting withdrawal symptoms like crack  just post something, please  

We had bad icy weather too, so better safe than sorry  looking forward to your next jaunt, whenever that will be

On Monday, January 02, 2017 at 10:04 AM, JeffB said:

Congrats on the new handle. My first 2017 jaunt will come soon.

I'm getting concerned now... its been a week...  

Brussels

New year, new me! A more appropriate name as I prefer my skirts to heels... looking to see what ensemble yiu had for new years, dont keep us in suspense!

Wow! Lost for words. I love the skirt, booties are a nice touch as well. Just fabulous. I have been looking for a skirt that colour as well, and I hope its thick tights in this weather! ♡♡♡

Love it ♡♡♡ super cute as always, love the way you are girlishly fiddling with your hem in the second pic as well - I do that when I'm nervous too. Combo looks good, but lose the leather jacket. A yellow hoodie and a blue denim skirt would look great as well. Looking forward to your next jaunt  

3 hours ago, redandwhite said:

I had no idea that I ever inspired anyone! I take that as a big compliment. Thanks !!

I have always liked that skirt! Suits you, Jeff! No jaunts over Xmas?  

Looks great, Jeff!  Tights again are a nice touch  

Looks great! I like the skirt length too!  

You look fabulous in that rig! I think the mini skirts are fine if you have thick tights, or in your case leggings! Cute booties too  A much more youthful look. Though being the prude I am, I would have gone for a knee length denim pencil  

Looking forward to your next jaunt  

No jaunts this weekend?  

I am sure you will find a blazer that will suit you. I am a size 16 in blazers but a 10/12 in skirts. Its tights weather here, super jealous of the unseasonal weather you are having. Though it was 40 den thigh highs and boots with a pencil skirt yesterday with temps in the mid 40s Farenheit, and I was warm enough. Some girls were sans tights which I thought was crazy

Looking forward to your next jaunt  

I would tuck, I know underwear is not discussed here but something snug should take care of everything. Seeing as girls worry about "camel toe", I think a man's bulge is something that would not look good in jeggings / leggings so anything to sort out your, ahem, cargo is appropriate if you choose to wear such. I wear a skirt so if I am in a formal pencil skirt then I take care of how the contour of my skirt is... I thought the thread was about tucking the jeggings into boots... 

8 hours ago, JeffB said:

In a good way, or a bad way. Don't keep me in suspense!

 

 

I got my voice back now... I wasn't so impressed with the denim jacket and the plaid skirt, I would have gone with a cardigan and blouse for such a style of skirt....

Today, a much nicer look... jacket and skirt suit each other, though I would have worn a longer skirt like a 24 inch one (but I'm a bit of a prude like that  ) and I don't wish to flash, though I would go with black knickers too if I was wearing something so short. Its just part and parcel of wearing a skirt. My legs arent as nice as yours so I am more self conscious... Nice you got a compliment, surprised someone as smart as you isn't on LookBook or other social media  wish we had summer like weather here, definitely tights weather, and all the winter skirts are out and the summer stuff packed away   though I did some errands in my dark grey denim pencil today, went without tights even though it was the low 50s farenheit  

Loving the top as well, a dressy yet casual ensemble  

Lost for words...

On Friday, November 18, 2016 at 9:14 PM, JeffB said:

 

1 hour ago, Thighbootguy said:

The color combination looks good but the skirt makes you look like you should have skipped lunch.  The top of the skirt flairs out and that does not flatter your figure.

Glad you voted... it gives you license to complain/rejoyce about the results (in another forum).

I would have voted that a straight skirt would have come up Trumps with those booties  this one just is unflattering and destined for the thrift shop IMHO  do the booties come in brown? Might have been a safer bet. Autumn leaves and muck from the street may tarnish these. They are cute though, but better suited to a beige pencil dress teamed with brown gloss tights  

On 10/30/2016 at 9:22 AM, JeffB said:

Jaunt #339, 10/29/2016: A few days earlier, I swapped out my tank tops and short sleeved shirts for long sleeved shirts and sweaters, and wouldn't you know, temps would reach 70 after a chilly start, and because it was a wee bit nippy, I went with my blue denim jacket over a long sleeved red t-shirt, a 24 inch black skirt, gray tights, the Payless "Martinez" booties in black and a black satchel bag.

Absolutely love this look! You've nailed it with the grey tights and the skirt is so nice! Don't worry about what image is presented, if you dress, comport yourself, adopt mannerisms etc that is seen as female, then so be it! It must have been so natural and not forced, that no one notices anymore. When we are just busy enjoying ourselves and not worrying what others think we relax and that's where the successful jaunts are!

23 hours ago, Thighbootguy said:

I think you meant TBG and I'm not missing earrings as I do occasionally wear them.   However, earrings and fem glasses frames (which I have suggested) probably don't fit into JeffB's goal of, "I don't want to LOOK like a woman, I just want to DRESS like a woman!".  I was just pointing out that JeffB's short hair style is close to a style some females wear so it shouldn't be too much of a surprise that he doesn't attract too much attention when he just gets a quick glance from a casual observer, especially from the back.  The other possibilities are that all the folks in the KOP mall are too wrapped up in themselves they wouldn't notice anything, or it is the most tolerant collection of people ever assembled.

Haha, I did mean TBH as in To Be Honest - earrings will go with the clothes, but as he says, not his style. But some women don't peirce their ears or have never done so, so Jeff fits in that segment. A little relaxer (hair straightener black girls use) may be on the horizon

But if you walk about nervous, and unsure or furtive then you will garner stares as a guy dressed as a woman. So his sassy attitude  (as displayed by loads of black women) will mean very few will challenge the way he is dressed. I admire the confidence though I think some shots out and about rather than the usual bedroom window would be great! Asking a passers-by to take my picture helped me start conversations with others when I started my brief jaunts while skirted. I took advice and tried to improve my look and I think Jeff looks great.

Sorry Jeff for talking about you like you are not there, I think the next step is to go to work in your skirt, the first time was nervous for me but a knee length black pencil skirt and black tights generally went unnoticed  (a few teasing remarks from colleagues but they lost interest after 10 minutes), and I wore flats rather than heels... this was on a dress down Friday and I forewarned my boss...

Once again,  you look great, even though button down skirts are not my bag

3 hours ago, Thighbootguy said:

Again, a well done great look.  You're going to make me a fan of longer skirts.

JeffB look at your pictures.  You (and the regulars on this board) see a guy in a skirt and boots, but to a casual observer it is real easy to miss the guy part.

Consider the following images from Good Housekeeping  One  Two  Three

Your just another one of the gals.

I do like your style, but you are missing earrings TBH. I think a more youthful skirt will suit you, but I enjoy your jaunts. I know of a guy in Southampton who doesn't even bother to trim his 5 o clock shadow before donning a micro mini corduroy skirt and green tights before going on his jaunts, people mention his, erm, "interesting wardrobe". Still, you make an effort and look smart. I think as you blend in, no one's going to object, though a more masculine top, even a polo shirt teamed with a pencil skirt or a men's sweater would make more of a distinction that they are looking at a guy in a skirt

Look forward to your next ensemble, but I never was a fan of button down skirts as I fear of wardrobe malfunctions when crossing my legs  

On Wednesday, October 12, 2016 at 9:44 AM, JeffB said:

Henri1942 & heelsrus2000: Thanks for the kind words.

No problem! I'm going to get my Zara knee length grey pencil on with some stockings, its halfway between tights weather or shave and go without or wear pop sox. Might treat myself to some shoes as well. Looking forward to your next jaunt for fashion advice ♡