A black dress from Delia's with a butterfly pattern and yellow piping on the collar. Life-changing. I wore it with a black headband and black slide sandals with a heel shortly after getting my braces off, and this is the prettiest I can remember feeling in high school.
A gray Hanes t-shirt under a burgundy wool v-neck sweater vest, both pinched from my dad's bureau, with thrift-store Levi's and a ball-style chain as a necklace, like the chain that connects a pen to a desk in a bank. Round-toe brown shoes.
A lavender off-brand polo shirt with pink stripes from a thrift-store, with above Levi's. Blue skater Van's. Possible additions: baby barrettes, a bubble necklace. Not this kind of bubble necklace, but a little bottle of viscous soapy water from which to blow bubbles, on a cord.
Same as above but with a baby blue men's Izod (alligator) shirt, worn to trash, and a necklace with tiny rainbow-colored beads.
Sage-green men's swim trunks (again, salvaged from my dad) with a drawstring, notches at the side of the leg, and white piping on the bottom, the lining torn out. Gray Hanes t-shirt. White flip-flops or tan two-strap Birkenstocks. (These were my favorite shorts for years.)
Denim overalls over a bodysuit with brown and green stripes and a row of henley buttons on the scoopneck. Round-toe brown shoes.
A white guayabera with rainbow-colored fruit embroidered on the front panel. Levi's and Vans.
A loose, sheer white maternity blouse (my mother's from the late '70s) with a split Mandarin collar and pastel embroidery (flowers) on the front panel. Levi's. Hair up in a bun with wooden chopsticks. Jelly shoes!
A pink plaid pencil skirt with a little matching belt and a short-sleeve, ribbed black turtleneck sweater. I think this skirt might still be in my closet. Same black slide sandals as above.
Blue and black plaid trousers with a flare at the ankle and a tab waist. Same black turtleneck as above. Round-toe black shoes that looked like Mary Jane's without the strap. Again, these might still be in my closet.
A vintage black button-front blouse with slim vertical rainbow stripes, salvaged from my paternal grandmother's closet (still in my closet though I haven't worn it in years). Black boot-cut pants, black high-heeled boots.
A sage-green cardigan from the Gap with mother-of-pearl buttons, worn as a pullover, buttoned up, nothing underneath. Thrift-store Levi's. Moccasins, no socks.
Vintage Levi's, off-white t-shirt, and a turquoise beaded necklace and I un-threaded and re-threaded so I could put two pennies that my brother had pressed at the top of the Empire State Building on the thread, worn and reworn until the thread snapped. Moccasins.
Cropped white pants, a mauve crewneck sleeveless shell (one-half of a "Jackie" twinset, without the cardigan), white flip-flops. (You won't believe me but I was the first person at my high school to wear flip-flops as shoes. Revolution!)
A turtleneck sweater with wide navy and gray stripes, with fitted, stretchy, flat front navy pants (boot-cut of course, not skinny-legged) and brown loafers. The pants had a hidden zipper on the side and no pockets, front or back.
An off-white v-neck cable sweater from J. Crew (probably one of my all-time most worn items) with ugly light blue J. Crew jeans (boot-cut!) and moccasins or brown loafers. Silver hoop earrings. (I didn't like gold in high school, now I rarely wear silver.)
A long-sleeve, fitted cream-colored crewneck tee under a light pink, chunky wool crewneck sweater vest and a gray kilt (solid gray, no plaid; still in my closet but too small to wear). Strapless Mary Janes, sometimes with cream-colored knee socks.
As you can see I vacillated between grunge and preppy. I'd probably still wear about half of these outfits today, with adjustments made for fit and footwear. I could do a whole other post about outfits I remember my friends wearing.