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!