The Upscale Vagabond

By Frizell Bailey

One evening I was walking down Brady Street when a couple sitting on the sidewalk near Jimmy John’s asked me for some spare change, a fairly common occurrence. Usually, depending on my mood, I fork over whatever I happen to have in my pocket or say I don’t have any cash on me if my pockets are empty.

The pair was a young couple, probably in their early to mid twenties. Their black lab-ish dog sat next to them wearing a bandana. Given my situation at the time, the term “spare” change had taken on a much more literal meaning. Struggling to balance graduate school and a personal life out to kill me, working had become sporadic at best. I politely told them that I had no change to offer and continued on my way. But a block or two down the street it occurred to me that there was something rather odd about this down-on-their-luck trio. While the two humans looked sufficiently scruffy to be panhandling, the dog looked decidedly less needy.

What nerve they had, I thought to myself, to ask me for money when they have a dog that looked like it had never missed a meal or bath. The couple, I decided, must be dirty and un-kept out of personal choice, or to scam suckers like me for change.

This got me thinking about myself and my own situation. My well kept appearance belied the fact that I had no job, very little money, and no place of my own to live. Despite this I had managed, through the kindness of others and other more creative means, to fairly closely maintain my standard of living. This was the genesis of the upscale vagabond.

The Ethos of the upscale vagabond.

The upscale vagabond ethos was borne out of necessity. Since college I have acquired certain tastes. Though not quite caviar in scale, my personal likes are definitely not the ramen noodle tastes of my undergraduate days. Needless to say, even though I was temporarily “down on my luck,” I had no desire to return to this lifestyle. Upscale vagabond existence is about living above your means, but without actually paying for it. It’s about being able to sip suds or martinis when you can really only afford fountain drinks with free refills.

It’s who you know.

The adage “it’s not what you know but who” applies not only to getting a great job, but also to having a fun and fulfilling social life, especially when money’s a little tight. When you’re broke is not the time to be timid or introverted. Trust me, people will exchange cocktails for lively conversation.

On the question of libations, the first thing you want to do is chat up your bartender. They’re at work so they have to be there. And especially if they are working a shift alone, they’re probably jonesing for a little conversation, particularly with someone who is not either tanked out of their mind or trying to put the moves on them. Doing this will probably score you at least one shot or a brew on the house.

Don’t stop there, though. The second thing you want to do is chat up the bar patrons. It is important, however, to remember that same gender patrons will probably yield more success than the opposite gender. If you’re a guy it may seem like you’re trying to pick up someone and if you’re a girl you may seem like you’re looking to get picked up. But if you do go down this road, be sure to keep the conversation away from anything that could in anyway be misconstrued as sexual. The goal is to get a drink, not laid.

This may all seem kind of shady, like you’re taking advantage of other people’s generosity. This is incorrect thinking. You are not overtly asking for anything. They want to buy you a drink. Besides, you will probably find that some of these individuals become good friends, or at the very least good acquaintances. And isn’t that what any night, or late afternoon, at a bar is about anyway?

You look marvelous.

Just because funds are low doesn’t mean you have to look like a bum. When it comes to clothing you want to spend $20 but look like you’ve spent $200, or at least $50. Thrift or second hand stores are great, but resist the temptation of making these items the foundation of your wardrobe. You want chic as well as cheap. At thrift shops what you’re looking for is that one (maybe two) special item. Grab that funky long sleeve button down.

Next, you want to hit big retailers that specialize in fashion foundation items. I have three favorites: The Gap, Old Navy and Structure/Express. However, don’t buy anything that has their logo on it or any item they happen to viciously promoting. Proceed straight to the sale rack. When shopping the big boys you’re looking for the staples, jeans and plain tees. However, do keep and eye out for items that look like they shouldn’t be in The Gap, Old Navy, or Structure/Express. Sometimes they’ll surprise you.

When it comes to boutiques, only go in if they’re having an insane sale. Treat them like thrift shops. You’re looking for something unique for cheap. Shoes, unfortunately, are a little more complicated issue. Inexpensive shoes are easier to find if you’re a girl. Just wait for a sale or go to Baker’s. For guys, it’s not so easy. Men’s shoes cost retailers more, so even when they’re on sale they are nowhere near as cheap as women’s shoes. The upside is that they last longer and don’t go out of style five minutes before you take them out of the store. Them’s the breaks.