What to Wear For Your Next 90s Night, Inspired by Pop Culture Icons

In case these ads haven't already shown up on your Instagram feed, a massive celebration of all things 90s is coming to Williamsburg next weekend. But unlike every other 90s night you've been to, this one will have actual, real-live celebrities from that decade, including performances by Coolio, Lisa Loeb, Salt N' Pepa, and Smash Mouth. Smash Mouth.

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In honor of the occasion, we've put together a guide on how to dress like you've stepped right out of a Naughty By Nature concert—oh yeah, they're performing too—inspired by five style archetypes from the 90s. Throwing on a choker just won't cut it this time.

The Dorky Sitcom Character

Staunchly principled yet irreverent and lovable, dorky 90s sitcom characters tended to wear loose, easy clothing you'd likely find at a flea market. Notable examples: DJ Tanner, Phoebe Buffay, and early-seasons Miranda from Sex and the City (when she wasn't wearing her fancy lawyer-lady pantsuits).

H&M beaded vest, $50; H&M jersey top, $10; Zara strappy dress, $50; Birkenstock Cocoa Nubuck Arizona, $135.

The Hip-Hop Starlet

The flat stomachs of music stars certainly got their share of appreciation during the 90s, with everyone from TLC to Gwen Stefani highlighting their abs by pairing tiny crop tops with exaggeratedly oversized pants. Lucky for 2015 imitators, JNCOs just released a new Heritage collection.

American Apparel shiny sleeveless crop top, $18; Converse Chuck Taylor All Stars II, $70, JNCO Heritage rinse-wash half pipes, $70.

The It-Model

The surest way to look like a model It-girls of the 90s? Wear as little as possible. In fact, all you really need to look like Kate Moss is a naked dress (ideally paired with black underwear and a notably absent bra), a dressed-up choker, a strong cat-eye, and sky-high pumps.

Steve Madden Prariee booties, $140; Topshop necklace, $18; American Apparel sheer jersey chemise, $24; Make Up For Ever Ink Liner, $23.

The Cute Goth

Misery became oddly adorable when Christina Ricci played Wednesday Addams in 1991's The Addams Family. Though most recently refererred to by Kim Kardashian in her poorly spelled yet strangely poetic email to her mom about wearing too much "omish shit," the cute goth girl is an easy one to pull off, considering dresses like the one pictured below seem to be on the racks at nearly every major fast-fashion chain this fall.

L'Ecole des Femmes dress, $249, available at Cloak & Dagger; OCC Lip Tar in matte, $9, Dr. Martens Lana boot, $130.

The Privileged Prep

Besides the two most obvious examples (Cher Horowitz and a 16-year-old Britney Spears in a certain schoolgirl uniform), the 90s were full of upper-middle class girls twirling wads bubble gum and making well-researched arguments about why they deserve a new pair of Jimmy Choos. See: Hillary from The Fresh Prince of Bel-Air, Bianca from 10 Things I Hate About You, for instance. And the type isn't without its contemporary converts: One could argue Charli XCX—and, to a certain extent, Taylor Swift—are modern examples.

Claire's necklace, $12.50, American Apparel fuzzy crop tee, $58; Lazy Oaf cat gingham skirt, $78, available at American Two Shot; Jeffrey Campbell Inaba heels, $135.