Ha, this thread is absolutely hilarious. A bunch of 30-50 year old men from the mid-west giving fashion advice. 1999 called, it would like to have it's Sketchers and cargo pants back please.
Also, the Brooks Brothers links are absolutely ridiculous. $400 for a sweater vest Mmmmmkay! If you can't come out of Target/Ross with a pimp outfit you don't have style and paying 10-20 times as much for a sweater isn't going to change that. It's mostly about being able to match the right colors/style/proper fit, also dressing age appropriate but within current style is important. I am in my 30s so I don't wear skinny jeans and flat-hats, but I do make sure to pay attention to current trends and add pieces that aren't ridiculous.
To the guy who lives in SD who posted the atrocious old man leather boat shoes...WTF dude? You live in Southern Cali... it's Vans, Sperrys, or flip-flops for you son.
Also, REI is only fly in Colorado. That shit won't pass on the coasts. Guys from Colo crack me up, your standard issue black North Face fleece has probably gotten you laid here, but that magical power stops at the state line.