GUESS Originals takes a moment to celebrate the life and heritage of one of the most iconic models for not only GUESS, but the fashion industry as a whole — Anna Nicole Smith. The 32-piece men’s and women’s collection will be available beginning October 7th, 2021, in select GUESS retail stores and GUESS Originals pop-ups globally — as well as guessoriginals.com and select styles at urbanoutfitters.com.


The GUESS Originals x Anna Nicole Smith Collection by Cali Thornhill Dewitt takes a look back at the renowned GUESS imagery. The collection and marketing were designed in collaboration with artist Cali Thornhill Dewitt, who helped create the 2018 “Did You Miss Me?” Anna Nicole Smith GUESS Originals Capsule. Cali Dewitt was born in 1973 in British Columbia. He is a multidisciplinary artist who lives and works in Los Angeles.


The campaign features Euphoria and White Lotus star, Sydney Sweeney and recreates previous Anna Nicole Smith shoots from 1992 which were directed by Paul Marciano and shot by Daniela Federici.

The new campaign, starring Sweeney, was shot by Kenneth Cappello in Malibu, CA, with creative direction by GUESS’ Brand Partnerships Director, Nicolai Marciano.


“Anna Nicole Smith is essential to ‘90s fashion. Anna’s legendary beach shoot revived for this collection and the campaign with Sydney Sweeney is the perfect timeless moment to continue to celebrate one of the most iconic GUESS Girls with a new generation.” — Nicolai Marciano, Director of Brand Partnerships.


The collection, inspired by the hues of the ocean from the original 1993 Miami photoshoot by Wayne Maser, uses teal as a key color, and blends in classic tones of black, white and red. Anna Nicole Smith’s signature is digitized into each style for a special touch, as well as Dewitt’s iconic phrase “Did You Miss Me?” These unique personal details, combined with both vintage and classic silhouettes create a moment that is both true to Anna’s legacy as a style icon and the zeitgeist of ‘90s GUESS trends.

The men’s collection offers a selection of long and short-sleeve tees, sweatshirts, crewnecks, hoodies and a black denim jacket and matching pant. The women’s capsule features an array of tees, mesh shirts, bodysuits, sweaters, sweatpants, crewnecks, jumpsuits and include a matching gingham jacket and pant as well as a teal denim jacket and pant.

Made with a combination of water base and discharge inks, photo reel graphics from Anna Nicole Smith’s never seen before 1993 calendar are printed on a variety of tops and tees in both the men’s and women’s capsules. An assortment of hats, totes, socks, sunglasses round out the collection and polish off each look.

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