LaVan, you would never look stupid!! You have such amazing style, you could carry your things in a pillowcase and you would still set the bar very high!
But I dont think the JPG is the right bag for your needs...What about the LA bag? or a clemence GP? My laptop fits perfectly in the Whitebus, but that bag does not go over my shoulder, but then, it might go over yours, as I am definitely not elfe like!! LOL...if only!!
Or, ...evelyne GM? Depending on the size of your laptop? I am not sure if you are an evelyne girl, but honestly if you are commuting, it is such a comfortable bag...Basically I am just free associating....but anyway, the JPG seems like it is not quite the thing...though I agree in parchement it would be amazing!