SkirtDude

I generally wear booties in spring and boots in winter, so I have no real advice on flats, but, make sure your flat is not too high up the tower block and is near some decent shoe shops

Nice look, Jeff! Perhaps the little girl in the Food Court was staring at your sandwich out of jealousy, lol  You look super casual, this is the look I go for when shopping.i guess the more confident we become, the less anxious we look, and people pick up on anxious vibes.I guess one could look furtive and jumpy in trousers or jeans and people would stare, so just go out and be confident. It's not an outlandish outfit, just a skirt and top, so it's not going to catch the attention of most people anymore. Especially as the world of fashion seems to be embracing men's skirts, thought it's a while for it to reach the shops from the catwalks, it is happening little by little

Looking forward to your next jaunt for inspiration! Something just as youthful, please  

On 7/6/2017 at 9:43 AM, JeffB said:

Good suggestions. I'll see what I can do about trying them out.

On 7/5/2017 at 11:59 PM, HappyinHeels said:

JeffB,

Since you already look fabulous standing up yo should try some photos in a seated position. Or stand close to a wall and raise one leg halfway up to accent your shoes just like the women do. How about some outside shots?? You get all over SE PA and South Jersey so there is no shortage of chances to do this. Think about it.  

a seated position like this, including your skirt is good.

On 7/4/2017 at 4:10 PM, JeffB said:

Thanks for the kind words. I do strive to look stylish and tasteful when it comes to what I wear in public. There's a certain....something about those long, gauzy skirts I've sported that really makes me feel feminine when I wear them.

"Moderately conservative" works for me when it comes to my attire. I like to dress up as it makes me feel good inside, case in point, when it comes to tops, I've gone out of my way of late to wear openly feminine styles because I like how they look on me, I don't want to sport anything that looks even remotely mannish. I'm paying more attention to the jewelry I wear and, thanks to you and the gift you provided, I refuse to leave the house without earrings. Just another part of my evolution as a fashion freestyler. As for the museum, I'm already planning to return later this month, again, there's so much to see, perhaps I'll become a member and save on my trips there.

While feminine looks are good, I'd choose to dress like a young woman than an old one I think tight skirts are more feminine and sexy as they cling to your figure more, and for me, help me sit like a lady more as I keep my knees together. As for your poses, legs closer together is more tastful and less, er, "mannish"... just look at any girl on lookbook in a pencil skirt, or even in leggings etc, and generally the knees are in close proximity... I would never stand as if I'd wet myself as for your camera, can you not get a cheap SLR like a Canon EOS which can come with a handy IR Remote that allows you more time to get into a pose and you can control when the picture is taken, rather than rush for a timer. I used to rush to get into shot, try to sit, cross legs and hope my skirt hadn't ridden up too much, tug the hem a little, and try and pose but it was a big ask in a 10 second window.

As for skirt designs, I would go for something cute like a skater skirt above knee length, or my favourite pencil cut with a generous slit at the back, wheras the longer stuff I would wear at home if around the house as it's not so flattering to me. You should definitely pierce your ears, and you need something to help fill up your tops, as "Old Salt" does on the other forum

Looking forward to your next jaunt

On 6/30/2017 at 2:10 AM, w6ish said:

i know i have posted this same photo recently but!

this is me:  bring on the summer time

Replace the shorts with a skirt, lol  

Looking fabulous! The chino skirt looks nice as well, though I'd wear it at my hips so it's a little longer. Nice earrings! Looking forward to seeing the whole gang in the shopping mall in their skirts and heels! I'm opening a Go Fund Me page for funds for the plane ticket over  I see you are slowly edging towards a regular pencil skirt as worn by us in the office  A pinstripe one would suit you, with a white blouse and court shoes  Looking forward to your next jaunt

2 hours ago, JeffB said:

Jaunt #376, 6/18/2017: 

Looking great, bae! All you need is a wig and a splash of lippy. A short relaxed hairstyle would suit you as well. Nice earrings too. You should wear some dangly ones. Love the skirt, it's a good length. Thought you'd break out the more ladylike fitted pencil skirt, but you keep us in suspense

On Thursday, June 08, 2017 at 10:44 PM, JeffB said:

SkirtDude: Regarding that picture, one of the skirts I bought last Saturday looked like the one you displayed, I just need a dressy looking blouse to pair with it and I'll have a great looking outfit. I take wearing women's clothes seriously and want to look my best in them. By the by, thanks for the suggestions.

I know the effort you go to, and I am sure it will look fabulous! I have been wearing formal pencils for years, and have had nothing but compliments. Denim ones are great for casual trips, like chino ones, but the formal skirt is very versatile, it would look good with loads of existing tops in your vast collection! I am an avid follower of your thread (who would have guessed?  ) and since quitting the other forum due to racist comments I have been keeping a low profile in general. But seeing what sartorial rabbit you will next pull out of the hat has given me confidence and ideas for my wardrobe too. I have also added back in regular guy stuff as I need balance as well.  A skirt suit would suit you as well, but I am keen to see your formal skirt, even a simple white blouse would look good with it. Team it with stockings (too hot for tights) and pumps! 

Looking forward to your next jaunt  

Great look! Chino skirts are great, a good stepping stone to formal pencil skirts  Those really do look like rose-tinted spectacles, as I can see a hint of pink reflecting off your glasses  The length is great, I wouldn't wear anything too short but a tighter pencil skirt would look great on you. Why not try a formal cotton pencil skirt such as what most wear to work rather than chino or denim? There are some nice ones about, in gray / black / navy or other colours that can still look casual for a jaunt, or can be dressed up for work etc (see attached) and the shoes are cute too. That's an image from La Redoute UK (posed by model), though I'm sure the likes of Sears would have these commonplace skirts for sale. I generally go for 24 inch, sometimes 27 which I think can still look great. Less is more, a longer skirt looks good rather than one halfway up your thigh... I also stand with my legs closer together as well. I'm still a guy but that's how I'd stand in a skirt 

I think the look would suit you...

8 hours ago, JeffB said:

Hmm! It never occurred to me that a change in clothes could span such an age difference, but yeah, I can see what you're getting at, from Saturday's more staid ensemble to Sunday's more, well, risque outfit. Most interesting indeed!

I prefer Sunday's look to Saturday's, as it's taken 20 years off you! You've got the figure for the shorter tighter stuff and I think you shouldn't hide it away in unflattering crepe skirts but that's just my opinion. I wear denim pencil skirts just above my knee (23 inch), enough to be smart, yet if it's a nice fitted designer like D&G with a generous slit at the back, it's kind of sassy which makes me feel good. Shorter skirts are nice but I'm just worried with modesty, but you can pull off that look! I was wondering the same about your combinations, whatever it is you do it looks great  

Looking forward to your next jaunt

Great Jaunt, Jeff! A skirt like the lady in the background would do you well, as they are more youthful. I see you pushed the envelope with a picture outside. Ask the next person who takes your pic to get a whole shot, including your shoes and the rest of your ensemble  And as TBG says, earrings will complete the look, there are even clip-on ones if you don't wish to pierce your ears. Well done! 

On Tuesday, May 09, 2017 at 5:46 PM, Ray_Aber said:

Photoshopped - the light is wrong. Try again. You have just copied and pasted a photo (found on skirtcafe) onto a background. 

Trying to raise your post count, Ray? 

16 hours ago, Ray_Aber said:

http://www.dailymail.co.uk/news/article-4471836/The-glamorous-lawyers-Anthony-Bell-AVO-trial.html

Great look, SkirtDude!

However, it's not you, is it? It's an Australian female lawyer....

Just checking to see you're awake, Ray   

Jeff, Was it too breezy for the printed skirts? Didn't read of any Jaunts this weekend, which was a shame. I pushed the envelope at work and spoke to HR about my wardrobe choices, and after wearing skirts to work (corporate knee-length pencils), I thought I'd try a skirt suit! Teamed with red pumps, though the shoes were a killer. I need to get some more comfortable shoes, might even go back to booties as the heel is easier to walk in. First time with a handbag as well, but it was well received by colleagues

Looking forward to your next jaunt  

Very nice ensemble, cute skirt as well. You look better in more fitted clothes IMHO   the fact the women said you dressed nice was great, you really do plan well in advance, hence no stares, remarks etc as before. You could emulate Kate's style in TBG's supplied photo - the skirt looks nice  

3 hours ago, JeffB said:

My, my! I had no idea we had so many talented people here! I'm truly impressed! 

Jaunt #366, 4/23/2017:... I packed up and headed back to my car, passing two older women who looked me up and down as I passed and grinned at me, and I grinned back. I'm guessing they liked what they saw. Heh!

Hopefully, the weather will warm up more so I can wear a shorter skirt on my future outings. But then, I haven't worn a maxi yet and I want to squeeze in one. Ahh, so many choices, so little time! Double heh! More to come....

I'd look crepe in such a skirt, I'm jealous of your figure  but I like the idea of your maxi skirt... I guess you wanting to squeeze into one hints at a Kardashian-style tight calf-length pencil skirt? I think that will look really good if you did, and it seems the ladies like your ensembles as well

I bought a nice tartan pencil skirt which was just £1 on ebay! (pic below) It reminded me of my old username when I first joined HHPlace  

Still I cannot wait

To read soon of your next Jaunt

Here on High Heel Place

1 hour ago, Thighbootguy said:

Nah, just a clunky poem.

"Haiku" is a traditional form of Japanese poetry. Haiku poems consist of 3 lines. The first and last lines of a Haiku have 5 syllables and the middle line has 7 syllables. The lines rarely rhyme.

Winter dull and dark
High hems and Spring raise hopes
Tall boots even more

Where's the weekly post

Of your trips to shopping malls

In your boots and skirt?

On Tuesday, April 18, 2017 at 9:39 AM, JeffB said:

So, was my alter-ego shocking enough for everyone? 

Pumped: Wearing guy attire with heels got seriously boring for me, thus my migration to women's wear. I probably would've stopped heeling altogether if I hadn't.

I think you look great in skirts, I am still learning, most of my inspiration has been this thread! I think it's time to break out the shorter stuff now Spring has sprung! Sadly in the UK, Winter is back, so dug out the tights and wooly sweater, even wearing two slips under my black skirt today! Looking forward to your next jaunt  

3 hours ago, JeffB said:

Many thanks. I do as best I can. Meanwhile, because you asked:

 

You really are dressed as a woman as you're wearing blue jeans! The shoes are cute too  

8 hours ago, JeffB said:

Jaunt #362, 4/1/2017:....

Love it! I think the skirt really compliments the top and looks great! Maxi dresses are nice in summer, but can be annoying due to their length, some are past ankle-length so that can mean walking on your hem a little  Midi dresses are my limit but I think I am aiming more for the excellent look you've presented above. I always wonder if I'm being "un-seen" rather than not being paid attention to, but it's better than stares or name calling as well. I like that denim pencil skirt you've got there, I had one in a lighter shade from Zara, but a former friend stole it (when I was in pictured earlier in your thread with the frayed hem skirt I wore). I bought myself another grey pencil skirt this week, but it's more of a formal affair. Looking forward to your next jaunt  

Everything okay? This thread has been dead for days.  

You look fabulous! One way to push the envelope is ask a passer by to take your photo outside  I like the skirt length too. Looking forward to your next jaunt  

I haven't...

http://www.dailymail.co.uk/news/article-4235920/Hairdresser-banned-pub-Big-Brother-audition.html

but this guy was. I would have been cold dressed like that in this weather  

Jeff, I've always liked that frayed hem skirt of yours, you do well to wear it in the dead of winter! I've been in my pencil skirts which are snug and warm with tights. Looking forward to your next instalment

Jeff, Hurrah for proper boots! Nice skirt too, I still personally don't like buttons at the front of my skirts, but the image you present is very smart. I think I would choose warm boots over any heeled ones as it's just good to feel comfy... You should team your riding boots with that cute grey pencil skirt a jaunt or two ago