Share your best Freestyle Fashion pictures here.

[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.

[Dawn HH]

I quite concur with JeffB and Heel D. Put that outfit on, go out in daylight and tend to your business as usual and don't look back. When it is over you will wonder why you didn't do it a lot sooner. Looking good. Good luck! Cheers--- Dawn HH

[gony]

Last week i have bought 6 pairs of a brazilian brand called Via Uno... I spend 150,00 Reais (aprox US$65,00) because they are 70% off. I take some pics of two of them... I hope you like...

Thx

http://s177.photobucket.com/albums/w238/melissa_doramilla/

[kneehighs]

^ nice shoes.

However, photos of just shoes is not the focus of this thread. The focus of this thread is streetstyle outfits of men in heels. We'd love to see pictures of outfits you wear on the streets or plan on wearing on the streets though. And if you want, feel free to PM me with pics, I'd be happy to help.

Lets show how we take our outfits with heels out onto the streets--and still appear as men in the process. The goal of this thread is to inspire other members to overcome their fears of appearing in heels in the streets by preparing their physical appearance in advance--in the style and fashion sense.

Fear is after all really just a signal that we must all at some point in our lives deal with. Its probably like taking a 3 year old to the grocery who does not want to go shopping with you. You wouldn't let a 3 year old's mentality run your life. Since its groceries, you'd just take the child along with you and deal with it. Fear of wearing heels in the street is probably much the same.

Streetstyle and fashion lies at the heart of this thread.

Here is what I wore today. I am not styled for the picture--notice how my black pants are bunched up over the shaft of my boots. This is exactly how you would have seen me on the streets though, so the character of my photo is perfectly preserved.

Here is another pic taken on Little West 12th Street in the Meat Packing District.

[JeffB]

Yo, kneehighs! Regardless of if you were styled for that pic or not, it's still a great, casual look. More power to you, my friend!

[gony]

Well, Ok... Here are some pics with my outfits...

...

[NewfieGuyInHeels]

Love the outfit Kneehighs. I was out to the mall yesterday in the outfit below, I never saw anyone looking at my feet at all. and as i was walking I caught a look at myself in a mirror in the housewear dept. of Zellars and my heel was fully visable while I was walking.

[Danielinheels]

Now that's a sharp outfit! Kudos to you, Newfieguyinheels!

[kneehighs]

Newfie--I think you could pull that outfit off in almost every social context imaginable. The chunky heel, platform sole, and round toe camoflouge their the sex they were originally manufactured for.

[canadianbeaver17]

I love those red/clear thong ones. Clear shoes, done right, can look classy and sexy! I got a pair of Ellie 5" mules that are very comfy and look great, but I like to keep those for the bedroom. Too bad my gf always hogs them!

[canadianbeaver17]

It took years (and mostly being lazy), but I finally took some new pics of me in shoes. My gf and I just went away to Niagara Falls for the weekend. We both just needed to get away and do nothing! This is now our 3rd time there together. We like the fact that you get a half decent hotel for cheap. Plus, you're in a toursit trap! lol

I didn't bring any guy shoes with me. Not even like running shoes that look like guy ones. For driving and just walking around, I wore my Coach optic flats. I love these! Her and I loooove Coach! My gf bought them for me because she knew I wouldn't buy them for myself (they were just under $100 CDN). I have wore these out before to shopping and such at home. Only got one comment from a customer in Aldo's who really liked them.

I bought these peep toe pumps at 5-7-9 in the states at the end of the season. The make is Rouge. They are 4" high with a 1/2" platform. I know these are those same cliche pumps you see, but I like these because the platform is hidden on the sides. AND, they aren't shiny patent leather. PLUS, they are super comfortable!

I wore these out to dinner one night, with what I had on in the pic but a brown top (same style). There were people smoking outside. They just looked at us like "hey" and then went back to their convo. When we walked inside, about 5 staff members were there and no one did anything out of the ordinary. Well, I lie, we were both looking good so I'm sure they were just checking us out.

These mules are by Frederick's of Hollywood (my fave make - I got a few pairs by them). They have a good 4" heel. These fit like a dream. They are the perfect around the house shoe. I've been waiting for warm weather to wear them out. Normally, I'm sketchy on mules because most of them flip up too much which causes the pant leg to get caught under your foot. This is ok with flat mules or flip flops, but not really sexy with what you want to wear with them. Surprisingly, these don't flip up that high and work well with flare jeans.

So those are some updated pics. But now you might ask, "Well, CB17, what was the reaction?". None. Nothing at all. I was in all predicaments: standing in the entrance at a resturant waiting for tables, in men's washrooms, seated at visable tables, etc. There was even a couple of men's oldtimers hockey teams there. No one said boo.

Now, I'm not saying it's easy. It's easy in the sense that people do not really care what you wear. For me, it's more me being a tad nervous on trying a new style, such as the peep toe ones I did. But once you tried, it works well after that.

Wow, I went long, but I hope everyone enjoys them!

[Katrina]

CB17, I love that last pair...those are awesome. I also LOVE your french pedicure...I love that look on fingers and toes!

[kneehighs]

CB17 Love it. Not only in terms that you used this thread correctly, for posting entire outfits that you wore, but for you finding the time and energy to share your pics with us! Thanks.

In my view, I think I like the outfit in #2 the best. The brown top you said you wore probably complements your skin tone well, and probably makes for a more monochromatic dark colored image. Good job!

Excitedly looking forward to seeing and hearing more from you.

[HeelD]

CB17 - firstly, thanks for sharing your freestyling pictures with us. You're certainly as I pictured you - looking stylish, well co-ordinated and carrying yourself well.

Outfit #1 - I love the flats. They work well with the jeans. Something I, as you all know already, would wear in an instant. I would love to have seen the whole outfit that you wore with those.

Outfit #2 - well co-ordinated. I really like your peep toes. I've considered wearing peep toes but not gone ahead yet. My girlfriend is a big fan of peep toes. You certainly pull them off no problems.

Outfit #3 - I like the mules. Very stylish. I'm sure they worked a charm with what you wore. I have some heeled and wedge sandals that I'm going to wear over the summer and I hope to not encounter the pant leg caught under foot scenario too.

Can I ask you CB17, have you had a pedicure? Your feet look well groomed. Getting a pedicure was one of the things I had planned to do in NY but unfortunately never got round to it. It's something I'd like to do.

I look forward to seeing further outfits and contributions from you in this thread in the future. It's great see more contributions.