1. Context, context, context
I cannot overstate the importance of a good sense of context. It's easy to get overwhelmed by the hideousness that engulfs the racks: muumuus, tawdry christmas sweaters, stretched out bicycle shorts, and mom jeans. In your hurry to sift through it all, you might nonchalantly skip over your new favorite piece so try to make a day for yourself when no one is waiting for you and you can take your sweet time trying on everything. Get to know what looks good on your body, what would fit with your current wardrobe. Some ridiculous '80s sweater might look totally hip with your edgy haircut and designer ankle boots. If it tickles you, it couldn't hurt to just try it on.
2. Consider Alterations
Don't abandon that pristine vintage cocktail dress simply because it's a size too big. Maybe you love the color and cut of that blouse, but the sleeves are obnoxiously puffy. For the measley $3 you're spending, it would be worth it to take it to a tailor. You'll be surprised with how excited you'll be about that piece once it is exacted to your specifications.
Get creative! I thrifted this teal velour nightgown for $3 and altered it to be a mind-blowing cocktail dress just by lopping of the sleeves and a few feet of hem.
3. Shop Off-Season
Think ahead and shop for summer items in winter. You’ll find the best deals and have a better selection to pick through. Winter coats are plentiful and purchased for pennies in Tucson in August. The same would go for vintage sun dresses during January in Vermont.
4. Find Your Local Thrift Outlet
Most well-established thrift store "chains" like Goodwill and Salvation Army will have outlets for your thrift-stalking enjoyment. A magical land where all clothes are $1-$3 except on, you guessed it, half price days. The ladies at the Goodwill Outlet told me their clothes only get one week at full-price store racks before they get bundled up and shipped to the outlet.
5. Wear Your “Thrifting Uniform”
Be prepared for long fitting room lines (or possible lack of fitting rooms) by wearing something that is comfortable and easy to try things on over. I like leggings, tee-shirt style dresses, and slip-on flats. If you’re not wearing socks, at least slip a pair in your bag for trying on shoes. Not doing so might be characterized as gross.
If you know your body measurements, you can take an even easier route and throw a flexible sewing tape in your bag for taking measurements right there at the racks.
6. Don’t Stay Stuck in the Women’s Clothing Section
If you’re petite, check out the kids section for a shrunken schoolboy blazer or a little dress you can wear as a top. Or head over to the men’s section where you can find oversized cardigans or some nicely cut trousers.
7. Gravitate Toward Thrift Shops That Are Off the Beaten Path
Thrift stores in areas with a high population of hip college students will obviously be more picked over and pricey. Look for thrift stores near ritzy retirement communities and small settlement towns.
8. Get a Rapport Going With Your Cashier
Most thrift stores don't have a set-in-stone pricing structure so striking up a conversation with your cashier and telling them how nicely their orange vest brings out their freckles couldn't hurt, especially if you are going to be coming in on the regular. If the employees get to know you well enough, they may even be willing to set aside that elusive Pierre Cardin grampa cardigan you've been on the hunt for, before it is available to the masses.
9. Go Thrifting Regularly, and on Off-Hours
If you don't go thrifting on a regular basis, you're just asking to miss all the good loot. Thrift stores get new stuff every day, so be vigilant. You can even inquire what days the "new" merchandise gets put out on the floor. Get there early and be met with a veritable treasure hunt.