First things first- figure out where you're gonna go. Check out Goodwill and Volunteers of America. If you're not ready quite ready for down and dirty thrifting, try a vintage shop or a store that sells "gently used clothing". We like Rag-o-Rama. You're likely to find decent clothing at places like these but, be warned, prices will be steeper.
Keeps your eyes peeled for sales. My favorite Goodwill recently had a sale for 50% off of all womens clothing. Some stores have different sales daily and some stores have one day a week when the sales are super bargain-y. Get to know your stores; the more often you go, the more likely you'll score.
Go in with a strategy. I've talked previously about organizing your current wardrobe to narrow your focus when you shop. But there are other ways to get the most out of your trip. One way: set a budget. This helps you weed out the good from the great. When I'm second-hand shopping and I don't really need anything, I usually give myself a twenty dollar limit. If I don't do this, I tend to bring home a bunch of crap that usually gets re-donated. I have a habit of imagining myself wearing a particular shirt that would look really cute if it could be altered. Imagined-me is really productive and knows how to alter clothing. In reality, I've learned 10 out of 10 times I will not alter anything. So, if you're like me, only buy items that fit you and that you're sure you will wear. This is where the budget becomes helpful. If you are torn between several items, this forces you to pick the cuter, better fitting one, not one that needs fixin' up.
Shirt: $1
Skirt: $1
Shoes: $1
Total: $3
Shirt: $1
Shorts: $2
Belt: $.50
Total: $3.50
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