That's right - go right to the source. And no, your mom doesn't count. Try to find a woman close to your age who will give you an honest opinion. If you don't know any women, ask a stylish gay man. :) If that fails, ask the salesperson. Finally, as a last resort, visit an appropriate store and copy how the mannequins are dressed.

I know what you're thinking - this article of clothing is in perfect condition except for one teensy tiny hole - it would be such a waste to get rid of it when 99% of it looks fine. Doesn't matter. Ditch it. ONE exception - jeans. For some reason the 'worn' look is OK for them, although you're pushing the boundaries if your jeans have holes. But for every other type of clothing, worn = bad. The goal is to make you look like you take good care of yourself, and that starts with a well-kept wardrobe.

Be aware of the thermal properties of what you are wearing. For example, dressing all stylish with multiple layers is good - but if that extra layer causes you to sweat (forehead, or armpits), it spoils the advantage of layering at all. If you have oily skin consider washing your face when you go to the bathroom. Finally, you can wear an undershirt to mitigate armpit sweat-stains.

Yup, somehow you will have to live with the fact that you can't broadcast your latest PDA purchase to the whole world by strapping it prominently on your belt. Pocketing devices can be a drawback too - pocket bulges can be unsightly. If you absolutely must carry a ton of electronic gadgets around, check out some bag options in accessories.

This isn't really fashion per se, but it plays a huge roll in appearing attractive to women. As mentioned in the theory section below, women love a confident man. A confident, competent man is never slouched over like a senior citizen. Stand with a straight back. No need to be a military drill sergeant, but make sure your shoulders aren't hunched. Same goes for sitting as well.