You just need to get past the "image" thing. Image is fleeting and completely subjective. First you can either be the guy that goes for the popular, fad look or you can be yourself. You can look the part of the guy that has the newest fashions and even may look great and appealing to some but that's still not guaranteed. Besides do you want women or other people to see you for the clothing and style you wear or do you want a real woman that wants a guy that is actually nice, honest and treats a woman well (not talking monetarilh here either but respectfully) It's an old cliché to say it's what's on the inside but nonetheless it remains true. The lady you want is the one that met you talked to you and got to know you and didn't get hung up on image. That lady will also happen to be the one that isn't going to care about image when going out with someone so it becomes irrelevant.

You find a lady that picks you because you happened to look like you have a great image and that will just be a superficial person with whom a relationship will only last as long as your "image" remains pristine. You really don't want that.