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Shopping used and vintage clothing is a nice alternative to shopping the mass market chains; you won't spend as much, you'll be helping the environment, and if you play it right, you will wind up with a look that is current but not trendy. Keep in mind, though, that shopping used means being constantly vigilant; when you see something that works for your shape and your wardrobe, you will need to buy it right now, since it is probably the only one available.
If you like the hunt, though, here are some basic tips about shopping used.
Vintage Sandra Sage cocktail dress available at Etsy
You have three options when you shop used: vintage, consignment, or thrift. Where you shop will depend on what you are looking for, how much you want to spend, and how much time and effort you are willing to put into the whole endeavor.
Vintage stores often only take pieces that are 20 or more years old; some vintage stores specialize in a certain era. Vintage stores are most often the most expensive used clothing option, particularly for high-quality vintage pieces. Fashion trends are cyclic, which means that past trends are constantly being recycled; one way keep up without looking too trendy is to shop vintage. This fall, the sleek 60s are back -- that Jackie Kennedy sheath dress and jacket look. Vintage stores are a terrific place to find actual pieces from the 60s. Keep in mind that shapes and sizes have changed over the decades, though, so these pieces may require some alteration.
Consignment stores carry more current pieces; in fact, many have restrictions on how old an item can be. Typically consignment stores will be chock full of things from the last five or so years. This is a great option if you are looking for basics, like wool trousers or skirts, but you should steer clear of anything that is clearly a last-year (or the year before) trend. Prices at consignment stores tend to be lower than buying new, but not dirt cheap. And look for pieces with the tags still on; you will get a new piece at the discounted price. Consignment is also a good bet for formal wear, since no one really wears out an evening gown.
Thrift stores are catch-as-catch can. You can find pretty much anything at the thrift store, for next to no money, but you will have to work for it. Be prepared to dig through racks and piles in search of one or two things that will work; also be prepared not to find a single thing that does work. But keep an open mind at the thrift store, because you never know what you might discover under the junk. Unlike consignment stores, where there is typically a fairly high minimum quality standard, the thrift store has none, so check garments carefully for wear and tear and stains.
Need more specific guidance? BlogHer's own Mir has written the definitive guide to thrift and consignment shopping.
There are also a wide range of on-line vintage and second-hand shopping options. The dress pictured here is currently available at Etsy, for example. Before you buy on-line, though, check the garments measurements carefully. I would buy that pink dress in a heartbeat, except for the fact that it's way too small for me, at least according to the seller's notes. If a listing includes only a size, ask for actual measurements (bust, waist, inseam) -- a vintage size 8 may not be the same as a current size 8, and you want to know that before you buy.
No matter where you shop, assume that what you buy will need to be laundered or cleaned before you wear it. Check seams and fastenings carefully, and make any necessary repairs right away. Plan for alterations; a ten dollar cocktail dress that needs fifty dollars worth of alterations is still a steal, but not if you skip the alterations and don't wear the dress (or worse, wear it unaltered).
Finally, steer clear of disposable second hand clothes -- tee shirts, for example. If they are too worn out for someone else to wear, they are too worn out for you, too. Look for good quality pieces that have been properly cared for and are wearing well: dresses, skirts, jeans, coats,
