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Let’s start today with a definition because, clearly, we are all here to learn.

HOBO (noun): One who creates an illusion of homelessness. A tramp. A full-grown lady ready to make a statement. Often accompanied by a “long hair, don’t care” attitude.

Most of you might think to look rich, you need to appear well put together, wearing something designer, and showered. Most of the time, this is true. Except when you are trying to look so rich, you look poor. Let me explain.

My long lost twin sisters, MK and Ashley, have perfected this look through the years. Sewer-chic, garbage-bag couture, Fifth Ave. Trash — call it what you want. These ladies somehow make me want to roll around in a dumpster, cut arm holes in my down-comforter and strut out the door like I own this town.

No, Mom, I didn’t miss my appointments at the salon the past four months. I look like this on purpose. It’s called OMBRE…do you even know who Rachel Bilson is? 

Undoubtedly there’s an irony in paying more for distressed clothing, worn leather, and ripped jeans. But we live in a world where Snooki has her own perfume and grown women shop at Claires so really, it’s not all that strange.

Here are some of my favorite hobo looks. The more ridiculous, the better.

Now, the most important part of mastering this look is including one token amazeballs piece into your hobo outfit. This piece is what sets you apart from a true-life crack addict passed out on the curb. Maybe this is your Chanel shades, A. Wang purse, pet fox, or my personal favorite – the high end shopping bag. When I lived in Florence, I constantly observed sassy Florentians prancing through the piazzas with Fendi, Prada, and Gucci shopping bags day after day. How could they afford it? What was their secret? Then one day, a friend (who was equally as curious as I was) reported that she had looked inside of one woman’s shopping bag as she walked by. The content? A single sheet of paper…ridiculous and also genius. If you can’t make it, fake it baby.

For added personal amusement I highly recommend keeping your head down, sunglasses on, and appearing extremely bothered when rocking the hobo look. This way, normlie’s might mistake you for a celebrity/VIP. You know you’re owning the look when someone snaps a photo of you with their iPhone. This happened to me once in 2006 at a Los Angeles boutique and to this day, it is one of my favorite stories to tell…that and the one about my stint as a hand model (dead serious, buy me a drink and I’ll tell you all about it).

I know what you’re thinking. When can I test drive this look out without causing a huge commotion? Here are some great times to go hobo:

  • You haven’t had time to wash your hair (for the past week)
  • You’re on a party-binge or ridiculously hung
  • You’ve had a bad breakup
  • Your dating someone European (look at you go)
  • You’ve listening to “Creep” by Radiohead so many times you got yourself in a funk
  • You just did the Master Cleanse and all of your clothes are now 2 sizes too big. (I only lasted 8 hours on this cleanse which is supposed to last 14 days, for the record)

Important Disclaimer: This look is a total man repeller. Most men just don’t get it, even though dontilookrich does have a sophisticated male following. If you are single and desperate to mingle, hold off on this look.

What do you guys think? To hobo or not to hobo?