i think with any brand [even chanel or vuitton] you can find an out-of-date look. a lot of it comes down to personal preference but if i were you i would try to stick with a solid color and not a logo-covered bag.
again, it's totally up to you and your style but i think that bags with a lot 'going on' like logos, prints, or several colors won't last as long as something plain in a neutral color. i only buy bags in solid colors and classic styles and i never feel the need to get rid of them.
i love the longchamp le pliage nylon tote because it's classic, less than $150, easy to clean, and goes with everything.
here are a few other suggestions:
marc by marc tote [not as plain but big] $198
marc by marc turnlock [on sale from $448] $313
brahmin $225
eta: i refreshed the page and it reposted this, now i can't delete. sorry!