^ don't get that webgem. the less money you have and the fewer shoes you have, the more crucial it is that whatever you get is as versatile as possible. that saddle shoe might be a nice shoe to have as your fifth, tenth, or twentieth pair of shoes, but i would absolutely not recommend getting it as your first pair.
kenilworth: it's kind of a dressy shoe. i personally wouldn't wear it with jeans. i know you said you wanted sleek, but some shoes are too sleek to look good with casual clothes. this is a personal decision.
rapid city: it's pretty casual and would go great with jeans and khakis, but as you said, it's not very sleek.
other good, first timer versatile shoes:
- leeds in anything but black
- dalton in anything but black
- blucher wingtips such as the macneil.
- chukkas (not sure if AE makes them in anything but suede, which you said would be too casual)
- Rawlins in dark brown (it's similar to the Kenilworth but is on the #8 last); only seen it once at Nord Rack, but it's a great looking shoe
things not to get:
- anything black
- anything in a balmoral (aka oxford) style. too dressy. when you need a dress shoe, you'll know it. (possible exception: AE strand in walnut)
- anything that looks fun or eye catching. you want something that you can wear all the time and will just blend in.