Anyways, just barging in to take a peek of this thread.
Are we still on the 2003-ish era? I just remembered one thing. Since the setting is in Bay Area (SF Bay Area?), remember it's the center of dot.com boom/bust, so it's all nouveau rich look. Not your traditional establishment East Coast members-only look. You might be caught dead dressed in a designer suit. But if you were trying to be a tech executive, you might wear some brand name suit (Hugo Boss, Burberry, Gucci, maybe Paul Smith?) but don't be surprised if the guy matches it with a pair of sneakers.
And I am pretty sure he might even have a Palm V in his hand. I had one (don't know why I needed it). If you didn't have the money, you might have a Palm III. That'll surely gives some of us older readers some squeechy giggles. People bought those handhelds devices like smart phones are nowadays (and it couldn't even do nearly as much as a smart phone could).
And speaking of sneakers. Did you get to see my new Superstar?
Though I'd imagine myself seeing JJ wearing all black Gucci suit with a pair of traditional white Superstar with red or green three stripes, like these:
http://www.adidas.com/us/superstar-80s-vintage-deluxe-shoes/B35982.html
Though those are Superstar 80s in the link.... I think back in the early 2000s era, Superstar II was more like it. But probably not the more street cred black Superstar... (which the wearers of them often have them very worn and dirty). Though JJ probably would get a pair of limited release Fabrique en France Superstar rather than your ordinary Made in China ones. Though I am not sure if the made in France ones were available around 2003.
I just remembered I wore a Kenneth Cole turtleneck back in that era. You could probably top it with a four-button suit (I didn't, but some people would). Most of us college kids at that time wore very street stuff. Could be expensive, but still street looking stuff. Rich people in Bay Area liked Bohemian look (the well-off hippies look). Though I am not sure if that's more of a mid 2000s thing or not. You know the Urban Outfitters look.... There was this girl (who sort had a crush on me) digged the Anthropology (and possibly Free People), so I got her this vintage looking necklace for her birthday from that store. You know, the semi-precious stones and turquoise mounted on the oxidized silver settings type. As for guys, I remember someone told me, "shell necklace..., you think everyone is Californian or what?" But that was the look at that early 2000s era. T-shirt with shell necklace/bracelet (sometimes the bracelet worn on the ankles paired with flip flops). Possibly with a can opener as a decorative item on the necklace/bracelet.
And yes..., later on the decade, we got into the more frugal, recession era trend. Though well-off people would wear expensive stuff that looked like they were from thrift stores just to mix in. Of course that later turned into more of a hipster trend. Think Hayes Street of San Francisco.
EDIT: Just some addition of Bay Area culture. San Francisco culture is very organic and grass root. I am pretty sure most of you guys won't able to figure us out. We like our stuff non-mass commercial type, organic certified and sustainable. SF people carry Timbuk2 bags, drink Blue Bottle Coffee, and eat Super Duper Burgers. We like our San Francisco brands.
As for food, that's the era where everyone would brag about their latest find of cheap sushi restaurants. LOL