I want something which appeals to most fashion aware women in a heterosexual way

[Liquidus]



I used to be painfully shy around women, because I thought they'd only go for guys who were rich, attractive, smart, or funny. Then I realized I was all of those things.
True story.

 

[AlexE]



But now I am trying to get to know more women on the streets.

Women on the street? They usually do not care to much about you outfit, but insist on getting paid in cash.

 

[MyOtherLife]

This is an extremely creepy thing to do to anyone and especially to any woman.

It is not creepy if you use a big ass SLR though. They will think you might be a fashion blogger out to show the world how stylishly attractive they are. It's only creepy if you use your phone cam.
Slightly off topic pro-tip: next time you go to a restaurant (especially one of those new age/hipster ones), lug around an SLR and maybe a notepad or something. Increases your chances of getting great service since they think you a food blogger/critic.

Sunglasses spycam beats this.


http://www.geekalerts.com/spy-sunglasses-with-2gb-built-in-memory/

Problem is keeping your head still enough to get a decent shot....and no zoom unfortunately.

 

[b1os]



Problem is keeping your head still enough to get a decent shot....and no zoom unfortunately.

Well, I don't see a problem with that. For close-ups, just.. get closer. Totally non-creepy when done right.

 

[mensimageconsultant]



See. It's very simple.
You want to appeal to women. Do you think women like self-confident men? Yes? Good.
You dressed and were dressed (apparently) poorly for the last 30 years. And you didn't mind it, i.e. you didn't want to change it. In other words, you are and were comfortable dressing poorly. Being comfortable is a good thing! And now you want to change your dressing. Not because you want to dress better because you aren't happy with your clothings anymore -- you want to change the way you dress to pick up women. Do you think you'll be comfortable wearing a SC, fitting pants, a slim shirt, brogues (or whatever)? If you are not sure, then you shouldn't change the way you dress, because otherwise it'll look fake (and that's what it is anyways...) and you'll feel awkward. It is not contributing.
Like others already said -- lurk a little, get to know what you like. But you make it perfectly clear that you don't care at all about fashion and don't want to invest time or brain ressources (otherwise you'd have some vague ideas on what style you're aiming for -- and if it's only a rough estimate, like MC or SW&D). So what are we supposed to do other than giving you very basic advice (fit etc.)? Get a consultant for creating outfits for you.

Please ask specific questions about my figure and face so I can describe to you what I look like so you can recommend routes.

People asked, no public answer. No cropped-out-face picture either. No idea what you're currently dressing like.
@Gdot: All I get is: "I want to look good. I don't want to look gay. Tell me what to wear. I don't mind what. I don't let you know my body, my features. I don't have a budget, I don't anything. Just tell me what is looking good to women!"
Edit: What unbelragazzo said in a more eloquent way.

Basically yes, but he seems to be in Germany, which would make it rather difficult. There are German-based image consultants. It's possible there is one near him who does good work for men.

The general way to not look "fake" (or, maybe the bigger issue, feel fake) is to take the current look and modify it. Also, of course clothing matters with women. 1) For how it displays physical features. 2) For how it displays personality traits. It's probably more important for a man who lacks "game" (and some men won't have much game despite training). Women tolerate more awkwardness from men who look good, (Surveys actually indicate that women dislike men for dressing in a not-so-masculine way). Meanwhile, uncertain approaches from men who lack good visuals often come across as creepy and quickly turn into rejection.

Finally, he is welcome to privately send a few pictures, like he's done for others. Because curiosity has been piqued.

 

[blahman]



Well, I don't see a problem with that. For close-ups, just.. get closer. Totally non-creepy when done right.

Sounds fair. And if you wanna do upskirt, just duck and tilt your head. Easy peasy.