[DoubleF]

How much are you willing to spend and how far do you want to go I guess is another question even though it seems you can afford pretty much anything anyone is suggesting. It also does seem like you're looking into the range of replacing a ton of what you currently own.

Shirts: Try to get something with buttons if possible. Aim for something a bit stream lined and not baggy. You don't have to button it up all the way.
Shorts: Something with belt loops and no more pockets than the typical front and back pockets and probably not jean shorts. Also aim for something made of cotton cloth rather than polyester (ie: Chinos and Golf shorts).
Belts: Nothing that looks worn out and preferably nothing that clanks and squeaks like a tin pail. Leather is generally safe, but there's some cloth ones that are perfectly fine as well.
Socks: Ankle socks. It's also worth considering youth ankle socks which are easier to do below the ankle vs above the ankle.
Shoes: Sneakers are fine, boat shoes are fine, tennis shoes are fine brands that make dress shoes that also make casual shoes are generally ok too. I wouldn't really suggest a shoe that covers your ankle with shorts though.


Places to look:

- $ H&M/Simons: Decent value, varying fit and comfort, decently trendy. Just make sure to grab the semi casual/more formal stuff rather than their athletic stuff.

- $/$$$ Saks on 5th/Nordstrom rack: Full price is expensive, but there's some killer deals to be had on the clearance racks. Generally most of this stuff is closer to semi casual to formal. Fit and value varies on what kind of deal you get because of the varied brands. Also a damn good place for the right type of shoes you're looking for IMO.

- $$ Banana Republic: Decently trendy stuff. Decent value when on sale. Looking at their displays is generally a decent baseline of what you're trying to achieve. I'm not enamored with the quality.

- $$$$ Kit & Ace/Lululemon: Lulu's semi casual stuff is worth looking into and IMO is decent enough that it can pass off in the work place. Kit an Ace in general looks wise will work well in the office for your needs as long as it fits well. These two are of the higher end, but so fricken comfortable and ridiculously durable in comparison to most other brands. It's more expensive, but IMO, I'd highly consider trying it out before eliminating it as an option. Oh and if you need dressier pants for the office, Lulu's ABC pants look good enough to be office acceptable, but are as comfy as lounge pants.

- Ankle socks: Consider looking into the youth socks. I personally think the ballet slipper socks for adults looks really weird. IMO it's a bit easier to buy a smaller sized youth sock that sits on or just below the ankle than an adult sock that does the same thing. Try to find a sock that is stupidly stretchy for the best comfort. I suggest going to winners and see what they have. The Body glove ones for youth is a great one to look at if they have any in stock. The youth cloth ones that aren't stretchy enough work fine, but I find that they sometimes pop off your heel and scrunch in the shoe which is annoying.

EDIT: For the ensemble you're looking at, I think you can probably get away with around $80-200 per ensemble for everything you need to buy. The Lulu/Kit and Ace might roll closer to $300 per ensemble, but there's some serious benefits and durability levels that aren't available in the lower end clothing IMO.