But you know what's helped a lot? Laying down a few specific, straightforward rules, to be observed every time I plan on buying something. And while I realize these aren't exactly earth shattering, they've been extraordinarily helpful to me, so perhaps they'll be of benefit to you, too!
RULE #2: LET GO OF THE IDEA THAT EXPENSIVE = GOOD, INEXPENSIVE = BAD.
But there are also reliable basics to be found at these stores if you're willing to dig through the trendier pieces. My favorite swingy cardigan - $12! - is from Forever 21. And I have a cropped H&M cotton blazer that's perfect for summer.
Take a look at your wardrobe. Do you notice an overarching color theme? Could this mean that you, too, unconsciously (or, perhaps, consciously) gravitate toward what works best for you?
RULE #4: TAKE CARE OF YOUR BASICS FIRST BEFORE YOU MOVE ON TO THE FUN STUFF.
Is this the sexiest way to shop? No! It would be much more fun to blow all my cash on some rad, esoteric contraption of a dress at an overpriced Lower East Side boutique. But being an adult means spending one's money judiciously. And that means, if you notice a hole in some essential aspect of your wardrobe, you've got to take care of that before you unleash yourself upon the Brooklyn Flea Market or go crazy at a Tory Burch sample sale.
Two important things to keep in mind when vintage shopping: 1.) make sure your find can be worn in a way that modernizes it (this may mean you'll have to swap out the buttons or have it hemmed shorter or whatever) and 2.) remember that the label means nothing! One of my favorite pieces, a navy blue wide collar jacket, is from "Styled by Rudy." I have no idea who Rudy is, but I'm a fan of his work.
RULE #6: FEAR NOT THE SPARKLE.
I wear sparkly jewelry to the office everyday. Sparkly clothing, though, is a different beast entirely. Matte sequins, like the ones that adorn this Anthropologie jacket, work for day - but probably not in a corporate environment. Approach with caution.
My point, though, is that many women consider jewelry - especially their nicest, most expensive jewelry - to be something that should be reserved exclusively for special occasions. It's not! If something makes you happy, you should wear it everyday.
If acquiring these wonderful, outrageous things also means making the occasional mistake (I'm looking at you, ugly secretary dress), so be it. In my mind, it's worth it.