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Sunday, September 22 Style

Top 5 most memorable Gap commercials of all time

During CEO Mickey Drexler’s time at the company, the Gap became known for its innovative commercials and ad campaigns. Here are Style’s top five favorite commercials.

5. Audrey Hepburn skinny black pant

When footage of the late film star Audrey Hepburn dancing in the movie “Funny Face” was used in a commercial advertising the return of Gap’s skinny black pants, it raised some eyebrows: Would the woman who was the muse to couturier Hubert de Givenchy really have been shilling for the Gap if she were alive? Whatever your feelings, the commercial is pretty unforgettable for how it mixes Hepburn’s 1950s choreography with rock music.

4. “Everybody in Vests”

In 1999, a group of models and performers including Alex Greenwald, Rashida Jones and Jason Thompson memorably sang the Madonna hit “Dress You Up” in a commercial launching the Gap fleece vest. It was as warm and cuddly as the product it advertised.

3. Madonna and Missy Elliott wear Gap their way

Speaking of Madonna, when the Material Girl and Missy Elliott (two of the biggest stars in the world at the time) mashed up their music for a commercial showing off the Gap’s new monogrammed jeans, it was an event. There was even a 75-second director’s cut of the ad that aired on VH1.

2. Sarah Jessica Parker and Lenny Kravitz “How do you wear it?”

SJP was at the height of her “Sex and the City” fashion icon status when she appeared in the “How do you wear it?” campaign, which showed off ways to style Gap pieces outside the usual preppy box. Her commercials with rocker Lenny Kravitz not only highlighted how she wore the brand, but also her dance moves.

1. West Side Story khaki vs. jean series.

What says rivalry better than the classic musical “West Side Story”? Instead of the Jets and Sharks rumbling, models in khakis and jeans danced it out to songs including the “Dance at the Gym/Mambo,” “Cool” and “America” by Leonard Bernstein with lyrics by Stephen Sondheim.

Tony Bravo is a staff writer at The Chronicle. Email: tbravo@sfchronicle.com.

Tony Bravo|Arts and Culture Reporter