Well, just for the record, I love the jeans hemmed for the red converse! I bought some of those Gap Long and Leans too, but had them hemmed for heels, and ....well, you've just pretty much convinced me that these jeans can also be worn with flats (well, at least fun/funky flats like Converse). They look so good on you that I'm about to run out and buy another pair of Gap Long and Leans and have them hemmed for more foot-friendly/comfortable flat type shoes.
In terms of work pants, and feeling like the look is kind of 'safe and boring' - have you considered some of the slouchy pants that Angie's been talking about lately? Now granted, I haven't yet worked up the nerve to try them yet myself, but I do love the *idea* of them, and you're a lot more fearless about these things.
I'm sure you saw it, but just in case you didn't - here's Angies "real world" Carlos Miele adaptation:
http://youlookfab.com/2012/03/.....tructured/
And how about her post recently regarding fabulous (full length and non-cropped) slouchy pants available at Ann Taylor?
http://youlookfab.com/welookfa.....y-trousers
In the meantime, good on you for getting some pants hemmed - I know this was a task that you'd been putting off...I do that too. (ah well...).