Share your best Freestyle Fashion pictures here.

[Krapsparov]

This is a pic I threw together in photoshop.

We had a rehearsal yesterday and I couldn't get the buggers to have a group photo. I sneaked pics on the sly and put them together.

As you can tell, the singer (far right) is not even happy about that.

Anyways.....

Black vest top

Trashed denim mini

Nearly black tights

Black ankle boots with small heel (always small when lugging stuff about)

[radiodave]

Very nice pictures, CB!

[canadianbeaver17]

Heel-D, I actually got fake acrylic toenails on my toes. My gf did them for me from a pack from a drug store. They look really good. I normally just wear a neutral color or pearly white on my toes, but I wanted to try this. Those are cool for every once in a while, but i prefer just straight subtle polish. About pedicures, I have been for them and manicures. I'm in the minority in saying I don't really like them. I feel I do a better job myself. Personally, I don't like the way they shape my nails when I go. I can assure you that even without the fake ones on me, my nails still look pretty damn good.

[NewfieGuyInHeels]

Hey all. I wasn't sure where to put these pics, but I hate starting a new thread for something that can go somewhere else. So this outfit isn't something I'd wear out, but it's an outfit none the less, so maybe someone here will like it. The denim skirt in the pics I made from an old pair of jean shorts, which is why it looks so ratty, I'm not much of a tailor I'm not sure what really goes with a Denim skirt so i just threw on a black ribbed T, and the shoes speak for themselves.

Oh by the way, I shaved my legs for the first time today! Go me hahaha.

I'm not really looking for approval on this outfit, I'm kinda just posting it for fun, lol, hope someone enjoys.

[NewfieGuyInHeels]

Now this outfit I deffinately plan on wearing out. I got the shirt from ebay and I lOVE the contrast between Red and Black, and I think my Pointed Nine West boots finishes the look nicely! IMO anyway

[HeelD]

^ Nice red shirt. Works great with the pants. Good outift. Regarding the skirt - if you ever do have to guts to out in it, I'd go with the boots because it looks better proportioned. I think the MJs will work better with a darker longer skirt or jeans.

[NewfieGuyInHeels]

Thanks HeelD, but like I said, a skirt isn't really my taste for out and about. Mind you I will admit it's nice for around the house. I made the skirt in the first place cause I was just curious what it was like, and I didn't really want buy one. lol

[kneehighs]

Newfie The red shirt, black pant, and pointy shoe combo look great! I can see you wearing that outfit in an upscale hotel restaurant/bar. Good color coordination there.

[JeffB]

NewfieGuyInHeels: Your red and black outfit looked good. You pulled it off quite well, and the Nine West boots with those delightfully thin heels tie everything together perfectly. Casual, yet stylish at the same time. Add a black leather jacket and the sharpness factor would definitely multiply. I have no doubt you can go anywhere in that outfit. More power to you, my friend! As for the skirt pics, you don't have to apologize for feeling that's not your thing. After all, you were just experimenting, and, to be honest, your efforts weren't too bad. Not every Freestyler can, or is willing to go to the next level of wearing a skirt, and there's nothing wrong with that. But at least you were openminded enough to give it a try.

[johnieheel]

Love the maryjanes! All 3 look ok to me but the last one with the black pants,red shirt and heels really looks nice. Good Job NewfieGuyIn Heels.

[admirer5577]

Finally I have made a pic of me. All you other guys have posted your pics here so it is about time I also do so. The lighting isn't the very best but I guess you can see enough.

When going to town this is what I look like most of the times. Kneehigh boots with a 4", tapered, heel. Sometimes 4-5" stiletto heeled boots or oxfords.

But to Torture Garden..... nah, that was a completely different outfit. (I might put up one in the fetish section some time.....)

[Pumps]

Very cool look, A

I just bought a new skirt. I've been looking for the perfect male skirt and this leatherlook skirt is damn close in my opinion.

If I was going to a fetishparty (and only then), I would wear boots and nylons.

[Pumps]

Or the more outrageous look only for fun:

[JeffB]

Pumps: Let me be the first to say your skirted look is pretty darn cool, especially the one pic with the leopard print pumps. Outrageous! More power to you, my friend!

[Krapsparov]

Yup!!! Thats a cool look. A guy could wear that skirt with no problems

[JeffB]

While we're on that particular topic:

I blame danielinheels for this (said with tongue in cheek). After seeing the pic he posted back on March 19th in the long black skirt he wore, I was so inspired by how sharp he looked, I decided on a crazy whim to give that a try myself, and that decision led to a happy reunion of sorts. Last week, I went to a high end thrift shop where I found not only the long black knit skirt you see in the picture above, but two pairs of the Renetti pumps I had given away well over a year ago, they being the black and black patent pairs. I absolutely couldn't believe my luck, coming across shoes I had sacrificed in my purge. It was literally a one in a million occurence.

The skirt was $12.00 and the shoes $10.00 each, and they were still in fairly good condition as it appears they hadn't been worn all that much since I gave them away. I guess there wasn't any need for size 14 women's shoes. So I took my new possessions home where, oddly enough, it took almost a week for me to get up the nerve to put on the skirt, even though I was behind closed doors and drawn drapes. Don't ask me to explain why, I can't, I was just plain apprehensive about putting it on. But eventually I did, pairing it up with a black turtleneck, matching belt, off-black pantyhose and the black leather pumps for my photo taking session.

I was nervous before I started taking the pictures, but I soon calmed down, and, as I did, I remembered just how much fun it was to wear a skirt like I had before when I previously posted pictures here, how comfortable I felt in it, and it shows in the pictures I think. Does this mean I'll eventually venture out in public in a skirt, probably not, like others here who've modelled skirts for pictures, I just don't have the nerve, so I'll be perfectly content to wear skirts in private for my personal enjoyment. With that in mind, let me know what you think about the pics, good or bad, don't be afraid to be honest with me. Thanks!

[Pumps]

Looking good,Jeff I don't understand why you're nervous about the skirt. At least in these parts a guy in a skirt is a lot more acceptable than a guy in pumps. I've seen lot's of men both on the TV and IRL wearing skirts, but never a guy in pumps (other than heelmeet of course). If you wear both a skirt,nylons and pumps then your outfit get stares. In public I usually wear either a skirt or pumps, but not together. That's just for fun. Or maybe fetish club. Also I don't get nervous wearing or taking picture, but uploading them to the web is a bit unsetteling:nervous:

[Elegant]

Looking great in that outfit, keep that up! (and I said that frankly, not ironically at all!)

[Danielinheels]

Oh sure, JeffB! Blame me, why don't ya

[Pumps]

Just went to do my monthly shopping in this:

Talked to one of my neighbourghs on the way. He seems fine with it, even though he's an older guy.

[JeffB]

Looking good,Jeff

I don't understand why you're nervous about the skirt. At least in these parts a guy in a skirt is a lot more acceptable than a guy in pumps. I've seen lot's of men both on the TV and IRL wearing skirts, but never a guy in pumps (other than heelmeet of course). If you wear both a skirt,nylons and pumps then your outfit get stares. In public I usually wear either a skirt or pumps, but not together. That's just for fun. Or maybe fetish club.

Also I don't get nervous wearing or taking picture, but uploading them to the web is a bit unsetteling:nervous:

To tell you the truth, I'm not sure why I was nervous either. Still don't why. But yeah, I would agree that the sight of a guy in a skirt, with or without nylons and heels would invite a boatload of stares, perhaps more, but I can't bring to wear one without the other. Like I said, I don't see myself going out in public in a skirt, so it's a moot point. Thanks for the comments.

[ShockQueen]

JeffB: Congrats on finding some of your purged pairs and being able to get reunited with them - you still look awesome! You just have that classy look about you no matter what you wear. Maybe it's that infectious smile? pumps: I like your "monthly shopping" pic there. Nice and comfy for a day out getting what you need!

[HeelD]

Pumps - that skirt actually looks quite masculine, like a kilt, so you pull it off quite easily. I imagine people did look but probably because it's so rare and unique. That skirt coupled with the plain black tee in post #657 works perfectly well. Glad your neighbour liked it.

[JeffB]

Shockqueen: Thanks for the kind words. I do as best as I can. Yeah, finding those shoes was quite the incredible stroke of luck. I still can't believe that really happened. Remarkable! HeelD: What I know about kilts wouldn't fill a thimble, but yeah, Pumps' skirt does have that noticeably masculine touch. And he certainly made it work well.

[Pumps]

Pumps - that skirt actually looks quite masculine, like a kilt, so you pull it off quite easily. I imagine people did look but probably because it's so rare and unique. That skirt coupled with the plain black tee in post #657 works perfectly well. Glad your neighbour liked it.

Thanks. That picture is currently rated 8.3 on Hotornot, so I guess it's a thums up in that look.

[JeffB]

Round two of yours truly in a skirt:

Just for fun, I thought I'd experiment with a knee length denim skirt, and this one I found at Sears fit the bill which I paired with a white turtleneck, off-black hosiery and my navy RSVP "Crysta" pumps. Why knee length, you ask? Vanity of course, I wanted to show off my legs! Heh!

Unlike the previous pics I took, this time, there was no nervousness whatsoever. I guess I'm getting more comfortable with the concept of wearing a skirt, and yes, I enjoyed the experience. Still, going out in one remains just than a fantasy. Or so I keep telling myself.

Anyhoo, give me some feedback, positive or negative. I'm a big boy so I can take it!

[Pumps]

That's a good outfit, Jeff . I must admit I prefer kneelength myself. It's a bit more comfortable. Most women, I've heard, who likes men in skirts say that just below the knee is best.

[Krapsparov]

I like the skirt length. If I'm wearing a skirt above the knee, I tend to wear boots to even it out. You do have great legs though. And that is coming from a hetro male LOL Cheers Jon

[JeffB]

Pumps: While I would agree that a longer skirt would offer more in the way of comfort, I just wanted to show off my legs. Like I said, this was all about vanity. Krapsparov: From hetero man to another, you've got good looking legs in a short skirt too! Heh!

[kneehighs]

^ At the same time though, this thread is also practical in nature. Designed to help guys develop freestyle outfits that they would actually wear on the streets...based on what they have seen other guys wear on the streets.