I like both Timberland shoes. You know, the bones of your current uniform are right on, I think, for tech (I work in tech too): Khakis, button-down plaid, black dress shoes.

Some rules of thumb:

• At least two pairs of shoes, which you should switch off wearing (it's good to let shoes get a rest between wearings, air out, etc.).
• Never wear white socks with shoes - white socks are only for sneakers.
• A leather belt. Get a brown one first. If you want a second, then you can get black.
• Go with conservative, straight leg trousers, not tapered. Conservative is better here. Make sure they break over the bridge of the foot - aren't too short and aren't too long.
• Plaids in blue/grey are better than multi-coloured plaids. Multi-coloured is more challenging and takes some fashion practice.
• You should wear a white undershirt beneath your shirt. No undershirt is sloppy.

One last - you can outdress your boss, but in terms of quality. You shouldn't dress above your boss - wear suits, when he doesn't for example. That would look silly.

Ok.