How to be a Holiday Pimp with only $20 in Your Pocket

Welcome to the holidays, folks. And whether you like it or not, with this joyous time of year comes a ton of pressure to drop a lot of dough on a lot of presents.

Here’s my problem with this time of year: I like giving gifts, but I hate spending money.

Lucky for me, I’ve found a way to scam the system. I can survive the holidays without spending half my paycheck in December or swimming through hoards of shoppers at the mall.

You think a $15 Old Navy sweater is a steal? I can take that $15 and turn it into three magical, personalized gifts for my closest friends. $7.99 for a scarf at Macy’s One-Day Sale? Please. I could snag a designer sweater for my mom with that cash.

And when I do, I feel like a baller. Like a Christmas Queen. Like a Present Princess. Like a Holiday Pimp.

Black Friday, eat your heart out.

There are a lot of different gift-giving personalities out there, like:

1. The Traditional – You’ve got a lengthy gift list, and everyone gets a standard but appropriate present. Some gifts are hits, others are misses, and you probably spent a little more than you wanted to.

2. The Homemade Hippie – You don’t have a lot to spend. Hope everyone likes hand-knitted Afghans.

3. The Gift Grinch – No list. No presents. No problem. Bah humbug.

4. The Holiday Pimp – You’re a young professional who didn’t have the foresight to save up for holiday gifts, and yet you end up giving everyone you love an incredibly awesome, personal gift.

I’d like to consider myself the latter.

The secret? Check out the video below. If you like second-hand shopping and the f-bomb, this is the video for you 🙂 (you’ve been warned!)

Can’t see the video? Click here to watch “Thrift Store” by Macklemore and Ryan Lewis

This might be the greatest ode to thrift stores ever to grace YouTube. Can’t say that I’ve ever found Gucci or fur coats at my Goodwill, but I certainly feel like a pimp after walking into a store with only a handful of cash and walking out with $100 worth of merchandise.

Thrift Store Holiday Swagger

It’s no secret that I’m a borderline thrift store junkie. But you might be thinking: “Sure, Steph. Thrift stores are fine and all if you’re the one wearing the clothes. But for gifts at Christmas? I don’t think so.”


In fact, gifts from Goodwill are more original and memorable, and inspire gift ideas you might not have had walking through Crate and Barrel. Plus, a trip to the thrift store can save you a fortune during the holidays.

Every year, I make a point of visiting Goodwill early on in my holiday shopping. But I can’t take all of the credit for my yuletide bargain-hunting tradition. That honor would go to my uncle.

The Original Holiday Thrift Store Pimp: My Uncle

My uncle was a notorious second-hand connoisseur. Growing up, he fed my artistic talents by keeping me well-supplied with all the art supplies my little-girl heart desired: a $5 easel from Salvation army, a 100-paint-brush set from the swap meet.

Sure, there were times when his purchases fell flat: a “designer” purse with a plastic handle, pair of wolf gloves, made of “real” (?) wolf hide, a chainmail backpack, to name a few.

Nevertheless, the man was a thrift-store shopping pro. He could take the change he found in his couch cushions and spin wonders. And each year at Christmas, my uncle would bring out the crème-de-la-crème of his holiday bargain hunting: a well-worn but none-the-less authentic Santa Claus suit. It probably only cost him a cool $20.

Now that’s a holiday pimp. I’d like to think his sweet skills were somehow genetically passed down to me.

My Goodwill Christmas Tradition

One of my favorite gifts I received from my mom was a pair of reindeer slippers she found at a small thrift store down the road. She glued big sparkly red noses to each stuffed reindeer face, transforming the cozy deer into festive Rudolphs. She spent maybe $2, and I wore them to school every December for four years.

Even as a young adult, I continued the tradition of thrift store shopping with my roommate. Every year we gave ourselves a $15 Christmas spending limit. We both loved Christmas and cared about each other a lot, but being the financially responsible (broke) young adults that we were, we decided to stick to the challenge and see who could stretch their dollar the furthest.

Oh, and we lived across the street from a Goodwill. So that helped 🙂

What seemed like an obstacle transformed into a quest to find the most meaningful, creative gift at our favorite store next door. We always ended up exchanging incredibly unique, thoughtful and homemade gifts.

  • A mason jar decorated with a snowman face and filled with marshmallows and cocoa for the perfect batch of hot chocolate
  • A brand new dish set to complete (and replace) our mismatched hodge-podge of dinnerware.
  • The coffee bean grinder we always wanted (secretly a spice grinder in disguise!)
  • Loads of cheap wrapping paper and holiday bags
  • Fabulous Christmas decorations: a Santa lantern, a box of unopened globe ornaments, a few strands of garland still in its packaging
  • The ugliest and most authentic holiday sweaters money can buy

3 Keys to Holiday Pimping on $20 or Less

If you skip the mall and start to think a little differently this holiday season, you can stretch your dollar to cover everyone on your list and impress the hell out of your cash-strapped friends.

1. Don’t give into the pressure to shop big

An iPad mini is certainly a gift your mom will appreciate and enjoy, but wouldn’t she rather have something personal and sentimental? Wouldn’t she be more comfortable knowing you put more thought than you did money into her gift?

2. Think creative and quirky

Don’t take your gift giving too seriously. Sure, you should be very particular about what you give to whom, but it’s easy to get caught up in your own expectations of what you should spend or what a great gift means. Small and memorable outshines flashy and generic any day.

3. If you’re worried, set expectations

Either don’t tell anyone you’re shopping second-hand, or make sure your family and friends know you’re on the hunt for something original and awesome… and it may happen to come from the thrift shop. And if you have a picky, rich aunt who would turn her nose up at a used French press, then maybe she should be one of the few to get a brand new pair of earrings.

Remember, wherever you decide to do your Christmas shopping, remember the spirit of the holidays: peace on earth… and Goodwill for shopping 🙂

Photo credit: Macklemore and Ryan Lewis “Thrift Store

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