First off I suggest buying the best you can afford, and make sure its what you want. I have a lot of bike clothes I never wear, but I found it on sale so I bought it instead of what I really wanted. The clothes the I really like have lasted me a really long time.
For shorts I'm super impressed with the new Yeti clothing line, and the black color shorts are subdued enough that you won't feel like you are advertising for them, the hard part appears to be getting the right size, and since they are hard to find that may be a huge issue.
I am also a fan of the Troy Lee Designs shorts, I have heard great things about the Ruckus and the skyline, but I like having a very breathable pair of baggies so I would suggest the Ace, which are super expensive, but I think they will last you years, especially if you buy the black color (cause they won't show stains). Troy Lee Designs® | Bicycle Pants & Shorts
My longest lasting baggy shorts are from Endura, they are kinda heavy weight, so they are best in spring and fall, but I've had them for 5 years and they still look new, I think these are newest iteration of what I have: Endura - Products
For spandex shorts I really like the Pearl Izumi Elite shorts, they have a somewhat thin pad, but once your as$ gets used to riding you will prefer thin pads cause they dry faster and don't wad up into a ball and try to cram into your b-hole. these: Shorts
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