I've never really known how to word this question, but I'm hoping this time I can sum it up a little better.

I was raised poor, and spent most of my early 20's working to maintain a simple lifestyle. I'm in my late 20's now, still struggling financially, but in school and working. I am attractive and dress well, but money has always limited my resources to some extent. Even of the better off men I've dated, most were very humble types that didn't put much emphasis on style or status. I never needed something I didn't have, and I never looked out of place with them.

I recently began dating a guy who I consider to be out of my league. He is very attractive and successful, and I sometimes worry I am not going to fit in to his world. I am always nervous that I will show up to a date unprepared or looking cheap. I know men don't typically care about your income as long as you're doing *something* with your life, but at my age, I don't want to be associated with the student lifestyle. I remember a few years ago meeting the colleague of an ex, and receiving a very abrasive response when I told her what I did for a living at the time. It was very embarrassing for me, and I often consider that this is the type of woman my date is interacting with every day at work. Women of higher classes probably have better resources and a more relaxed lifestyle than I do now, and it shows. I feel like I need to put myself on par with them, physically and in a social/confidence way, in order to make this work. Is there a way to do this, or am I looking at it the wrong way?