No Fashion Identity

[MVPlaya]

I have 2 pairs of jeans, which are pretty much always a part of my casual-wear.

For work though I have to suit up though, dress pants / dress shoes, nice shirt. No ties, except when I do big presentations or meet with high-profile clients.

Why don't you post what you normally wear, and where you would wear it too, and people could give advice. If there is advice on clothing that I like that always works well for me: a nice classy thermal with jeans and nice shoes (get those shoes that look like dress shoes but have sporty soles, they're comfy, last long, and always mix well into a casual outfit). Usual jeans / classy shirt. There's also a couple more flashy t-shirts that I wear with jeans for going out. I like leather sports-coats, can generally make an outfit more classy.

[Sanctuary]

It depends on where you're going, but as long as your clothes match and they look clean and neat you should be fine.

Bring a friend with you shopping who you can trust and has good taste. Or just browse around online. You're bound to find something you like. AskMen.com might be useful too.