Share your best Freestyle Fashion pictures here.

[Jue]

a "look" that would make it easy-peezy.

What do you mean by that?

I haven't gone street-heeling in around... 3+ years already I think. I've gone out a few times before, with my SO, in heels too. All those times, I wore normal tshirts, black usually, with super wide legged black pants, so the heels don't really show, even when walking, they show just a little bit. Haha. I've only seen one guy notice (Think he's gay, heh), while I was walking, and the look of shock in his face was priceless.

I'm planning to go again. Very soon. This week probably, to a mall. Gona see a movie with my SO. I'm planning to wear my 4.25 stiletto pumps, the one in my avatar, with black pants. For the top.. I haven't decided yet. I'll post a pic after goin out.

[HeelD]

Thanks for the compliments and comments guys, always appreciated!

Jue - you're looking great! It really suits you.

The HeelD Collection: Ballet Boy

The HeelD Collection: Feet of Gold

The HeelD Collection: Casual Cuisine

[NewfieGuyInHeels]

Awesome pics HeelD, You make the flats look so natural on a guy, I'll deffinately have to try them sometime.

But now I just got my new Nine West Boots, I wasn't expecting them until next monday. They're black, ankle high, pointed toe, with 3.5 inch stiletto heels. Here's just a couple pics I did wth one outfit, when I have more time I'll try more. As always I'm up for suggestions.

[HeelD]

Thanks Newfie! The pictures didn't come out as well as I hoped - a bit too grainy (I deliberately switched off the flash so I could get some more natural light shots). I'm still learning how to use my new camera - I'm gonna have another play with it in a couple of days. Those boots look great on you BTW!

[bootsnheels]

here is my collection

http://farm1.static.flickr.com/94/234867310_350c54b6b3_o.jpg

[gony]

Hello... my first pic post.. i hope i do right... Thx

More in my album: http://s177.photobucket.com/albums/w238/melissa_doramilla/

[canadianbeaver17]

Gony, I love it! Do you go out like that?

[Elegant]

here is my collection

http://farm1.static.flickr.com/94/234867310_350c54b6b3_o.jpg

Guess what? I really *love* the pumps with bright soles! The other shoes and boots are pretty darn sexy, too.

[johnieheel]

Adding a little color to my life!

[Mr. X]

Nice shoes Johnnie. I especially like the pink ones.

[gony]

Gony, I love it! Do you go out like that?

Not yet, but this year i wanna to go out with the first one.. i love them...

[luckyguy]

gony, you kill me... first your toenails are sick & your feet are what like size 9-10? AND you're tan!! You can fit into any type of heel & probably find any style you want. You are super lucky, love the photos. I am suffering from post-shave itchy leg day & it's not fun. But my new shoes are coming Friday... can't wait.

[gony]

Thx luckyguy, maybe im the lucky guy... My feet size is 10 for open shoes e 11 for pumps and boots. I always depilate my legs, but recently I am with laziness to do this. I have a lot of pics here, but my flickr album is full and i dont like the pics size in the yahoo... Maybe ill post new pics soon... Thx for all Gony

[NewfieGuyInHeels]

Just another pic with my new stiletto boots.

[Jue]

New pic! I'm goin out tonight with my SO to watch 300. I'll be wearing this outfit. It's my favorite so far. I think it's very chic.

[NewfieGuyInHeels]

Just did a couple more pics of outfits with my Nine West stiletto boots. Hope you all like, let me know if you have any suggestions or opinions.

I know I did this one before with another pair of boots, but I really like it so I thought I'd put it with these too.

and here with my Pleather Pants, black T, and tan/beige over shirt.

[Trolldeg]

Jue > Great pic! You are one of the few guys that can pull off thin pointy heels well.

[johnieheel]

Just did a couple more pics of outfits with my Nine West stiletto boots. Hope you all like, let me know if you have any suggestions or opinions.

I know I did this one before with another pair of boots, but I really like it so I thought I'd put it with these too.

and here with my Pleather Pants, black T, and tan/beige over shirt.

Very nice. Are those womens or mens leather pants? I have a pair of mens and really like them alot and look really great with just about any black heel.

[NewfieGuyInHeels]

Thanks johnieheel. They're mens faux leather (pleather) pants made by Tripp. when I first got them I hadn't bought any heels yet, so they were shorten for my flat and low heeled shoes (mens) But I still like them with my stiletto heels.

[johnieheel]

Thanks johnieheel. They're mens faux leather (pleather) pants made by Tripp. when I first got them I hadn't bought any heels yet, so they were shorten for my flat and low heeled shoes (mens) But I still like them with my stiletto heels.

They look great!

[JeffB]

Thanks johnieheel. They're mens faux leather (pleather) pants made by Tripp. when I first got them I hadn't bought any heels yet, so they were shorten for my flat and low heeled shoes (mens) But I still like them with my stiletto heels.

Well, I must say that's a damned sharp look, and you pulled it off perfectly! More power to you, my friend!

[Danielinheels]

Here's a pic I took recently with my newest shoes, wearing a grey mock turtleneck with a black high-waisted skirt. Note the definition in my arms contrasting with the relative slenderness of my ankles, but all working well together:

Here is what I wore during the day on St. Patrick's day, no comments as I spent much of the time driving before I turned back around and went to work:

[JeffB]

Great pics there, Danielinheels. I particularly like the first pic, quite a nice outfit which you put together well. You really look chic! It takes a real man secure enough in his masculinity that he's willing to wear a skirt, and look perfectly comfortable in it to boot. Bravo to you, my friend!

[davefry]

I was bored last night, so I took this picture. I think I look odd, but my wife says I look good. So, meh.

[kneehighs]

^ I second the opinion of your wife. You look good. You could easily wear that outfit on the streets, which is the purpose of this thread--helping others find outfits they can wear on the streets.

Your slender frame lends itself to heels and the square toe's will lend an air of non-chalance to your streetstyle efforts.

[davefry]

I feel I could wear the trousers out fine as I'm already comfortable wearing female jeans every day, anyway. I only bought them yesterday so I've not had a chance to wear them outside yet. However, wearing heels is another thing for me. I have worn those boots outside before very late at night, but I'm still not quite to the confidence level of heeling during daylight hours. It's frustrating, and a few times I've decided that I will wear whatever I want and if someone has a problem with that, I won't care. Except, I do care, unfortunatly. I think I need more night time heeling to bring my confidence up and keep it there, but I have to get up at 5:30am all week so it's not really possible. Oh, and ignore my bad hair, I had just got home for a shopping trip and I was a bit cream crackered.

[johnieheel]

Nice look! My style. You could wear it anywhere. No Prob.

[JeffB]

I feel I could wear the trousers out fine as I'm already comfortable wearing female jeans every day, anyway. I only bought them yesterday so I've not had a chance to wear them outside yet.

However, wearing heels is another thing for me. I have worn those boots outside before very late at night, but I'm still not quite to the confidence level of heeling during daylight hours.

It's frustrating, and a few times I've decided that I will wear whatever I want and if someone has a problem with that, I won't care. Except, I do care, unfortunatly. I think I need more night time heeling to bring my confidence up and keep it there, but I have to get up at 5:30am all week so it's not really possible.

Your story is no different from just about everyone else here when it comes to the apprehension that comes from wearing heels in daylight, not at 0-dark thirty at night or before the roosters wake up. It's all about having the confidence to overcome the nervousness and self-consciousness associated with such an endeavor, and yes, it can be very frustrating. Trust me, we've all been there, done that.

The only way to overcome those nerves is to simply go and do it. When you do, you're going to discover what we all have learned when it comes to wearing heels in public: no one cares. Ninety-nine of the passersby you'll encounter while on an outing are often too wrapped up in their own lives and affairs to notice or care about a man wearing women's footwear, and the one percent who do won't do anything more than stare or do a double take. That's it.

The very first time out in a public setting can be unnerving at first, no doubt about that, but once you've learned that it isn't the horror you imagined, you'll begin to develop your confidence which, in turn will spur you on to more and more outings. It doesn't happen all at once, but it does and can happen. Good luck to you.

[HeelD]

Davefry, go for it! It looks good. I guarantee you that you will pull that outfit off no problems. As Jeff says 99% of people won't even notice, the remaining 1% may double take but nothing negative. You may even get a compliment!

[davefry]

Of course I know you're both absolutely right, and thanks for the encouragement. It's just, I have one little problem, which I've posted about before, but still stands. Me and my wife live with my parents until we can get together a deposit for a house, and my parents are not excatly young. I think they would think it a bit weird if I wore that around them, especially if I was in heels. For other people, I really don't mind what they think, even if I do care, but my mum and dad don't need me to shock them like that. Maybe I have it all wrong, and they'd like it. Yeah, right. I'd still have to go past them to leave the house as at least one of them is home during the day. You have no idea how much I want to be able to be free, but until we can move out, it's not going to be easy to keep out of sight.