(LA Guy @ 14 Dec. 2004, 4:46) Your sister was being nice. I would say that her comment was that you tend to be overdressed for the occasion, and maybe tend to be a little uptight. I'm not saying that you ought to conform to the uniform, but you could wear something classy, but a little more toned down and relaxed than your avatar (well dressed for sure; but his expression suggests that he needs some Metamucil, pronto). Try corduroy or moleskin jackets instead of wool, and classic jeans with a cashmere longsleeve knit. And wear good quality, but old and well used shoes instead of immaculate Lattanzi's. It will make you more look more laidback; and you'll be surprised that you'll even feel a little more relaxed.
I think you'd be surprised to find out that I'm hardly overdressed considering the milieu. As I said, I go to high-end bars, not sports bars. I'm not walking in wearing Kiton, Alexander Kabbaz and Lattanzi complete with seven fold tie and beautiful pocket square -- I'm walking in wearing a casual sport jacket, pants and shoes or a suit and shirt with no tie. If that's overdressed then fine, I'll live with it. I'm not wearing jeans. As for "little uptight"? Ha ha, no. No one who knows me would ever say that. Being laidback is my life.
I'm a bit surprised at what I'm reading on this thread. Truly, personality and humor matter exponentially more than clothing, but I've never encountered a woman who thinks a good dresser is intimidating (that takes some hella insecurity). Of course, overdressing will make you appear uptight, but if Gorgekko is in a bar wearing a sport coat and trousers, girls aren't just going to run away in fear. Maybe the pants could drop an inch or two so that they aren't getting sweatstains from one's pits, but that should be enough. Secondly, Why would you dress poorly to make girls think that they have power over you in some area? From what I've learned, allowing the girl to think she has "power over you" in ANY area is a bad idea. Women don't respect submissive personalities (in clothing or not). Even if every single girl in the world is intimidated by sharp dressing (or being "stylish," which I see nothing wrong with), all you have to do is say "Hey" and show that you're relaxed, because in my experience, words speak louder than lapels.