And lots of women find glasses extremely attractive.Consider replacing glasses with sunglasses in summer and contacts in winter, not essential but many girls dry up when they see glasses.
Women don't have a hive mind, we have extremely diverse likes and dislikes when it comes to men, personality, and style. What one women thinks looks lame another will find adorable (I personally love the much reviled socks with sandals look), what one woman finds stylish and attractive another will find intimidating, or vane and desperate. At the end of the day beyond not looking like a homeless person the way you dress isn't going to have much impact on your chances of attracting women in general, it's just going to impact your chances of attracting women with specific preferences. You can spend all you money on buying fancy clothes if you want... but do you really want to attract the sort of women who care about that stuff?
All you need to not scare women off is to look clean and tidy. Things like a tidy haircut, neatly trimmed beard or clean shaven, neat clothes which fit you properly, and looking healthy, these can all be achieved cheaply. You can buy lightly used good quality clothes second hand, but to be honest I've discussed this sort of thing with a lot of my friends over the years and none of them would be ale to tell whether you spent $10 or $10,000 on a jumper, if they happen to notice that you're wearing a jumper at all (I wouldn't).
So, you're too intense. When first getting to know someone it's important to talk in a way that makes you easy to relate to. Speak simple English, talk about things that anyone can engage with, like the news, don't try too hard with the humour or being clever. Don't get me wrong, being smart is great and you certainly shouldn't dumb yourself down, but just hold back a bit, let the conversation end with the other person wanting to know more, not feeling overloaded. And yes, small talk is boring, but it is an important social convention which exists for a reason; it makes talking to people you've just met easy and let's you figure out if you want to make not-so-small talk with someone at a later date. Conversation is a skill, it takes work to get good at it.