Top 10 Rich People Who Look Poor

Emily Farris — Mon, 28 Apr 2008 13:45:00 GMT

When we were growing up, our mom always said "just because we're poor doesn't mean we have to look poor." But over the last few years we've seen people dressing like they're poor no matter how much money they have. Here we've compiled the top 10 rich people who look poor.

10. Peter Jackson
Producer/director Peter Jackson looks like he should be driving his El Camino (unironically) through the Burger King Drive Thru on his way to work at the video store. However, we do have to admit that this picture is old and he's looking much better these days; in fact, we'd probably make out with him now.

[Image via lightscameraaction.wordpress.com]

9. Penny Marshall
While it actually kind-of works for her, Penny Marshall doesn't exactly dress like she's raking it in from her big-time directing jobs.

[Image via lakers.topbuzz.com]

8. Tom from MySpace
Seriously, this guy sold MySpace to Rupert Murdoch for how many millions of dollars? You'd think he might want to change out of that t-shirt and put up a new picture. Maybe he could even afford a digital camera with a better DPI? Stop trying to be "one of us," Tom (if that really even is your name). You sold out a long time ago, and now MySpace sucks. The ads make it soooo sloooow. Do you have any idea how long it took us to grab this picture?

7. Si Newhouse
The Chairman and CEO of Advance Mags/Conde Nast is often spotted around 4 Times Square in "a well worn sweatshirt." While we could not secure photographic evidence of said sweatshirt, our many sources inside Conde Nast have confirmed this to be true.

6. Either of The Olsen Twins at Any Given Moment
While they're starting to grow out of it, the Olsen Twins defined hobo chic or boho or homeless chic or whatever the hell you want to call it. And if you've ever seen them wandering the streets of New York, you, too, may have mistaken them for malnourished homeless people who spent their $6/day sweatshop salaries on Starbucks.

[Image via tsl.pomona.edu]

5. Pete Doherty
Pete Doherty's look seems to always scream (or whimper) "Please sir, may I have some more?," whether he's asking for food, clothes or heroin.

[Image via news.com.au]

4. Nick Nolte
We don't think anyone will ever again think of Nick Nolte without thinking of this picture.

3. Britney Spears
There are just some things no amount of money could ever fix (though the Fiji water is definitely expensive, as far as bottled water goes).

[Image via socialitelife.celebuzz.com]

2. Trust Fund Hipsters
These kids spend a lot of their parents' money to look like they're forced to shop at the Salvation Army. The expensive coke also helps with the "too poor to buy groceries" look.

[Image via nochancepublishing.blogspot.com]

1. Amy Winehouse
Amy Winehouse is worth at least £10 million. She tops our list because not only does she look poor, she smokes crack, just to keep it real.

[Image via infdaily.buzznet.com]

Runner Up: Courtney Love
We know Courtney Love is supposed to be all Seattle rock grunge or whatever, but we really just want to give her some eye make-up remover and take her on a shopping spree (except we can't, because we really are poor).

[Image via nymag.com]

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Top 10 Rich People Who Look Poor