Vintage stretches across a varying plain of price points, from a $4,500 Chanel jacket to a BOGOF, tagless muumuu.  The lower a store’s price range, the more skort, starchy tourist t-shirts, and polyester blend suits in its inventory.  But don’t be afraid to get knee-deep in second-hand cast-aways, because floating in this fashion purgatory are timeless style pieces.  Successful shopping at these outlets merely requires a different eye.

I’ll give one example: I have a skirt that was once my aunt’s (circa early ’90s) with an elastic waist.  Don’t worry it’s neither terry cloth nor a waikiki Luau print.  It’s slate gray and pleated.  In the fall I’ll wear the skirt under a sweater paired with a slouchy vest or a collared shirt layered under a v-neck cardigan.  In the summer, I hike the piece up, transforming it into a strapless mini-dress, cinched with a snakeskin-like belt and worn under a light vest.

(A quick note on pulling this off: For this to work, skirts CANNOT be bias cut or pencil-shaped.  When worn as a skirt, the piece must hang free at the hips so the wearer can create her own shape/silhouette.  Also it helps if you have a smaller bust otherwise the skirt-worn-as-a-tube-dress-look may not completely cover the behind, spilling over into red-light-district territory.  We want to be edgy, but we don’t want to be that edgy).

Look beyond a piece’s original or intended function.  A ‘50s era ruffled blouse Susie Secretary wore buttoned up and tucked in a pencil skirt may look great open and un-tucked over a scoop-neck tank and skinny jeans.  A sweater-cardigan meant for a size 10 whose original owner paired it with elastic waist-band jeans and hospital-white tennis shoes may look sexy on a size 2 or size 4 as a slouchy, belted layer over a mini skirt.

That said, try whatever you look twice at on.  Even if something seems conventionally out-of-season, dressed up with your own spin, the piece could be what causes others to do a similar double-take on you.  And at bottom-out prices, we’re talking usually under $10 at places like the Salvation Army and Goodwill, there’s little financial risk if you have a couple misses.  Online vintage sellers like Etsy.com and Modcloth.com also make for great places to sift for character pieces.  Happy hunting!