I use my camera bag. It’s large enough for my 'blad and a paperback or two, plus for an overnighter I can toss in a clean pair of underwear and my toothbrush/razor/floss/gel and I’m set.
Here are two bags that seem to fit your needs. You can wear them across your body like a messenger bag.
dan, here’s the bag I bought for Mr. Tech for Fathers Day. He likes it.
Holy frijoles! $275!
I used to carry something like this for my camera, pda, cellphone, etc. Mine was from Eddie Bauer, but I don’t think they make them anymore. The previous link actually has a pretty decent selection of bags and packs.
Go poke around a big Army Surplus store. That stuff is cheap and it’ll last forever, plus it’s good and manly: no one will call it a “purse” if you take it out in the country and put a few strategically placed bulletholes in it.
Have a look in a camera store and get a small foam-lined hard case - I saw one the other day that was about the size of an A4 sheet and two inches thick.
I think they even have eyelets that you can attach a webbing shoulder strap to.
I’m going to check out a few places tomorrow. The first bag JuanitaTech linked to is appealing, though. I’m tempted, but $75 is too much to drop without looking around first. Thanks for your suggestions!
And Mockingbird,
Apple doesn’t, but eBay does. 
Speaking of eBay, I would think that would be a good place to look for something leather that has been roughed up a little.
A slight hijack, but how well do you like your American Tourister bag? I was looking at one today, and I fell in love with it. I’ll probably get it tommorow as a birthday prezzie (I’ll be 22. Whoo!). Unless of course you have stories about it randomly spontaniously combusting. Sponatiously combusting at regular intervals is alright though. I can plan to be out of the room then.
Other then a laptop I carry all my needed tech-toys (Palm, Nomad, headphones. The phone stays in my pocket), a few large books, cables, and what ever else I need in a basic backpack. I have a Jan Sport that I’ve been using for years and years and it’s still kicking. Your back will break before the leather reinforced bottom will
I second FyreFiend with the backpack idea. I usually have a book, an umbrella, a notebook, pens, my work badge and some other miscellaneous crap. I still keep my walet, keys and cell phone in my pockets, though. And I never take my bag with me when I go out to a bar or something, so it’s not quite the same as a woman’s purse.
A backpack, however, is just not as…polished, I guess. I get the feeling the OP is looking for something a little more professional and mature.
Of course, I could be way off base here.
Why not just carry a briefcase?
From the OP:
That’s cool. I have already been considering faking a limp so I could get one of those Bull prick canes.
I remember seeing a bunch of different sorts of bags at LL Bean and some at Land’s End. They’re mostly casual-professional style for the most part. Prices aren’t super cheap but they last forever-- I’m wicked mean to my luggage from Land’s End and it still looks new after nearly ten years now.
While at a local bike shop looking into the Timbuk2 bags, the clerk recommended the x-small version of a courier bag by Bailey Works. It’s very nice, and I’m leaning toward that one or one of the smaller Greene Street bags JuanitaTech posted. I’ll probably decide after this week, when I get paid. I appreciate all of your input. Thanks again!
JuanitaTech:
I didn’t really think about professionalism when I wrote the OP, but now that I think about it, it was in the back of my mind. Kudos for picking up on it.
FyreFiend,sycorob:
I have a Jansport backpack, but most of the time it’s overkill. It’s got way more space than I usually require, and the added attention I get when I go into a store is annoying. Recently, I had to make a rush for my bike (locked up across the street at a mall) when I ran late for a train. Quickly dropping my bag to remove my bike seat, anyone watching (like the nearby employee) probably thought I was going to swipe some books from the Barnes and Noble vestibule.
Emperor:
My American Tourister bag is very well-constructed. I “inherited” it from my father when he bought a larger bag, and have found it to be very versitaile. One feature I like is an expandable main compartment. A zipper runs around the middle of the bag. Unzipping it enlarges the main compartment and allows access to a “hidden” compartment. I’ve used it as a laptop bag, a weekend bag (where the expanding compartment allowed me to carry extra socks and a few other items), a school bag, and a few other things that escape me. Alas, it’s badly worn (clips are broken, the lining and some pockets are torn, etc.), which is another reason why I need a new bag.
Wus-Men, maybe. Real Men ditch the ‘Cell phone’ and add in the all-important pocketknife.
And don’t forget to grunt a like. Real Men grunt all the time, I hear. Although maybe they’re just constipated.
A lot, that is.
Besides, when out of the house I need to bring stuff to and fro work! How’m I gonna do that in my pockets, eh? My lunch won’t fit there!