1. The One-Strap Overall
As modeled by a fresh-faced, chain-smoking 20-year-old Kate Moss. Worn with a bandeau top underneath, or if you’re feeling really saucy (or crazy), nothing at all.
2. Spandex Bike Shorts
In fashionable polka dots, per Clarissa Darling’s instructions.
3. Crop Tops
We’re loving Kelly Kapowski’s floral number (and her oversized hoop earrings, too). It’s so … tropical, no?
4. Skater Gear (On Girls)
Check out baby Chloe Sevigny in oversized denim and a knit cap. So cute!
5. Crushed Velvet Everything
Yes to everything the Fly Girls are wearing.
6. Vintage Dresses
We’re totally digging Janeane Garafolo’s thrift store score, paired with colored tights and seriously high platforms. (Winona’s look ain’t bad either).
7. Babydoll Chic
Courtney Love totally mastered this look in ‘94, and she’s been rubbing it in our faces ever since.
Like the ones in Karl Lagerfeld’s Spring 1994 collection.
9. Babydoll Tees
In the ’90s, every cool girl wanted an shrunken babydoll tee from the X-Girl line. They actually fit us (unlike the typical boy-fit shirt). Also, Sonic Youth’s Kim Gordon made them. Kim Gordon!
10. Lisa Loeb Glasses
Apologies for accidentally getting “Stay” stuck in your head (again).
11. Bras As Outerwear
Somehow both Sarah Jessica Parker and Sarah Michelle Gellar made going out with nothing but a bra on look wholesome and not trashy. Okay, not too trashy.
Natalie Portman wore one in “The Professional” and made it look amazing, and we’re pretty sure girls were legally required to wear them to prom and Homecoming or something.
How sexy does this look?
14. Zip-Up Denim Vests
15. Tees Under Sundresses
A great way to winterize your summer clothes! (That’s a young pixie-cut-wearing Penelope Cruz, BTW).
16. Layering, Layering, Layering!
Only wearing a dress? Throw a vest and a flannel over it. Wait, you’re not done. You need a sweater and a crazy pair of tights. Okay, now you’re ready.
17. Sunflower Everything
Oh man, do we love this print.
John Fluevog designed shoes with the highest platform and the most extreme heels, to be worn almost exclusively by sexy space aliens and Deee-Lite’s Lady Miss Kier. Bless him.
19. Oversized Boyfriend Jeans
Drew Barrymore took the boyfriend jeans thing to the next level and paired them with a tiny, personalized babydoll tee.
Though, of course, it never left.
21. Silk Pajamas
Let’s take our leisurewear up a notch, shall we?
22. The Versace Safety Pin Dress
Liz Hurley wore it to the 1994 premiere of “Four Weddings and A Funeral” with then-boyfriend Hugh Grant. And, oh wait, Gaga already brought it back.