Iconic Gap Ads Are Back, Baby

Time for a trip down memory lane.

Photo via Getty Images

If you had asked 10-year-old me what I wanted to be when I grew up, I would’ve said, 1.) a TRL VJ, 2.) a Fanta Fantana if the VJ thing fell through or 3.) a person cast in a Gap commercial. What’s that? Why yes, I did watch an unhealthy amount of television as a tween, but I turned out okay!!!

As luck would have it, MTV announced just last week that TRL is coming back (nobody cared to tell me when the VJ auditions were), I no longer care about Fantanas and, just the other day, Facebook fed me (digitally, not literally) this new Gap ad. Again, nobody cared to tell me when that was cast, but I was instantly transported back into my family’s family room, clad in board shorts and a Wet Seal top, scaldingly-hot Bagel Bites in tow (always go oven over microwave), holding my pee so I wouldn’t miss the latest Gap commercial.

I’m a fairly emotionless person but I’m tearing up at the thought of getting excited for a COMMERCIAL. ‘Twas a simpler time, one that I need to revisit right now because I’m one cold brew in, it’s Monday afternoon and it’s 2017 overall. The Edward Enninful creation above is simply delightful: It’s crisp, it’s cool and I love me a Wiz Khalifa dance break as much as the next girl, but watching it didn’t direct my feet to the nearest Gap. Nay, it plunged me head first into the deepest of YouTube black holes to unearth my favorite Gap ads of yesteryear. I still have a mild heart attack when I see a velour tracksuit for sale, but this is one aughts comeback trend I’m embracing with open arms.

Below are 15 of my favorites. I dare you not to smile or laugh-cry at how ridiculous we all used to dress and how it’s all coming back and we’re doomed to make the same mistakes again, I DARE YOU!

The Slow-Panning Boy Band-Aesthetic Ones, AKA the genius that inspired this 2017 remake.

1. Vests

LFO meets Youngstown.

2. Cords

Backstreet Boys circa “Quit Playing Games (With My Heart).”

3. Leather

Backstreet Boys circa “I Want It That Way.

The Dynamic Duo Ones

4. Madonna + Missy Elliott


5. SJP + Lenny Kravitz


6. Juliette Lewis + Daft Punk

Also cute.

7. Claire Danes + Patrick Wilson

When Carrie Mathison was but a twinkle in Claire Danes’ eye.

8. Kate Beckinsale + Orlando Bloom

Remember how in love with Orlando Bloom/jealous of Kate Beckinsale I was in 2002?

9. Audrey Hepburn + ACDC

Get it, girl.

The Khaki Ones (Yes, there were that many)

10. Khaki Swing

Very Zoot Suit Riot.

11. Khaki A Go-Go

Pretty sure whoever choreographed this was watching the same movie the Rancho Carne Toros were watching during that triumphant choreography brainstorm montage with Torrance’s voice over.

12. Khakis Rock

Clearly before everyone figured out the real way to make khakis cool is to get Rihanna to wear them literally one time.

13. Pretty Khaki

I too enjoy being a girl.

The Holiday Ad (Sorry, I know it’s August but it mustn’t be ignored.)

14. Love Train

The G.O.A.T.


15. This Shannyn Sossamon One

This is almost too cool and should be running right now because everyone’s a DJ anyway right? Also, what happened to Shannyn Sossamon? And sorry, that’s it for now because I need to watch A Knight’s Tale right this instant.

Did you have a favorite? Or am I just a weirdo? Are you wearing khakis right now?

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  • Love it. I was obsessed with the Khaki Swing commercial back in the day. I wore khakis with black tees for a year straight. I kind of miss how much I used to love Gap.

  • Blythe


    • Also – 14 seconds into #14 🙀

      Hit rewind like 200 times to be sure.. but I’m PRETTY SURE 😵

      ! ! !

    • And #1!!!

    • Morgan Siggard

      She also rocks a millennial pink sweater in the love train holiday stripes clip. And I definaltey spotted a mighty ducks bash brother singing in the leather jacket ad.

  • dietcokehead

    Yeah seriously what has Shannon Sossamyn been doing since she left Warpaint?

  • Lebanese Blonde

    I remember being SO astonished at the Audrey Hepburn one and how the hell they managed to do that.

  • Shevaun

    Fuck that first vid gave me HARD FLASHBACKS to 2000 when I wore a ice-blue sparkly puffy vest over baseball tees and warehouse one distressed flares. thank you for this.

    also, the Audrey one, still good.

    • Kiks

      Oh god I literally had that exact outfit.

      • Shevaun

        OF COURSE YOU DID. 👏🏽

        I also had insane platform shoes, weird vests and many titanic-esque dresses.

  • Erin

    Let’s not forget the West Side Story era! I remember working there in high school during that time and I owned a pair of the floral cropped pants from that collection.

    • Niche

      I came down to the comments to say the west side story one is my fave. I think that’s the very best one ever. I remember telling my mom I *needed* coloured pants for school event so that I could get them. Lol

  • starryhye

    Thank you for this 90s and early 2000s nostalgia! I totally remember being swayed to shop at the Gap after seeing pretty much all of these. Then once I got there I remembered that their clothes fit like crap on me 🙁 I have not worn nor owned a pair of khakis in many, many years.

  • I never knew I could love a series of commercials so much.
    Also you’re so right – where HAS Shannyn Sossamon been?!

  • Arden

    Just had a severe flashback to buying my first ever “big kid” backpack from Gap – neon orange OF COURSE. Also those suede closed toe birks were everything.

  • Oh my god just here to say I am SO glad khakis are more or less not a “thing” these days! Also the Lenny Kravitz/SJP one brought be back to 7th grade like crazy!!

    • Abby

      And Gap khakis were impossible to wear without pantylines unless you wanted to wear a thong but WHO WANTS TO WEAR A THONG WITH KHAKIS?!

      • LOL oh god such a juxtaposition of sexy/not sexy

        • AbiTX

          I didn’t understand then and I don’t understand now why they refused to use a thicker cotton to make khakis. Why did they need to be made of paper thin cotton?

  • Amelia Diamond

    I still get get that Mellow Yellow / Mad About Saffron “Remix” stuck in my head ALL THE TIME

  • Kristina Klaffenboeck

    That first SJP one with the pink sweater and all the pins? FLASHBACK

  • Auriel

    DID I WRITE THIS?? (I might edit to add I wanted to be the girl on roller blades in the diet coke ad with Paul Oakenfold’s “Starry Eyed Surprise.”) I’m probably 20 views for each of those Gap ads on YouTube, and I try to casually work Rashida Jones’ appearance in mellow yellow/dress you up in my love/love train in conversation at least twice a year (ALSO BOSTON PUBLIC ANYONE?!?!).

    I watched a lotta TV as a child, tween, teen, adult. And now I want Pizza Bagels.

    • Um hi I bought roller skates at the beginning of summer and it’s 100 percent because of repeated viewings of that diet coke commercial as an adolescent.

  • rachel

    My mom was of the anti-TV variety, which means I have lived a full 26 years without knowing what a big part of Gap commercials Rashida Jones was until now. A true tragedy.

  • Abby

    I worked at Banana Republic during the Hepburn Back in Black campaign and they wanted some extra people to come in to the Gap and organize the store. I think “back in black” played once every 15 minutes.
    ETA: I too just recently watched A Knight’s Tale and Sossamon was SO KEWL but her character was eye-roll.

  • I guess I’m okay with GAP’s version of that decade? Because these ads made me dread less the oughts inevitable return to fashion. In fact, I even thought some of SJP’s outfits from the Lenny Kravitz commercial were cute! But I won’t be revising Paris Hilton’s version of the ’00’s. I just. . . I can’t.

  • Natalie

    Takes me back to a time when all you needed to be cool was a ‘GAP girl’ crewneck and bootcut jeans (extra points if you had the matching skinny striped scarf/haft/fingerless gloves combo)

  • The new Gap commercial is super slick, and any evidence of soul it may have had was lost in the hyper editing. All the celebs in the world don’t make up for the boring product the GAP has been peddling lately. Loved the charming goofiness of the older ones especially SJP and Lenny Kravitz.

  • CityMaus

    I could have written this myself! But my favorites were the Gap holiday commercials – remixes of pop songs about love, bright sweaters, fun childhood Christmases. Life was so easy in the 90s!

  • Selena Delgado

    forgot how much I loved this shit. thanks!

  • Emmie

    im pretty sure Shannyn Sossamon named her baby Audio Science

    • Thank you for this.

      • Emmie

        u r welcome

      • Also she was in a band called Warpaint for a long time(I know this bc I just saw them at Rock Werchter and apparently her sister? has taken her place in it or smth) and I gotta say they make A+ cool girl rock music

  • Andrea Alyse Pillaro

    Until I started watching these I did not realize how burned into my brain some of these commercials are! Both of the SJP ones and the Audrey one were like major style definers for my younger years…..despite not even knowing who SJP was because I wasn’t allowed to watch HBO or SATC #sheltered

  • Cristina

    This was amazing.
    I am confident SJP could still pull all those outfits off. She can do no wrong in my eyes.
    Man, Gap has such a way of making denim look effortlessly cool and relaxed, where now denim is an art form. A stiff art form.
    The Love Train is my fav because how cna you not sing at the top of your lungs and be happy?
    The new commercial is very 90’s-00’s United Colors of Benetton in video form and I love it.
    Yay Gap!

  • Jennifer

    Ugh. this was soo good.
    SJP is just a delight, love watching her sing, dance, twirl, etc.
    Juliette Lewis “white girl” dancing was adorable. Her smirk at the end says it all.
    Definitely spotted Rashida Jones in the second ad.
    Lenny Kravitz hair! It was so bad, it was good!

  • Missing my plus ladies!

  • erica

    Thank you so so much for this!! I’m right there with you loving these classic Gap ads. But you forgot the best one. Here it is. You’re welcome, ladies. https://www.youtube.com/watch?v=yT0ILtODaOA

  • Kezia

    The choreography in #11 is taken from Bob Fosse’s dance The Rich Man’s Frug in the movie Sweet Charity. We could all be better people if we went to clubs and danced like that.


  • C. Killion

    Great fun! Exactly what I needed while waiting for the plumber to come for bathroom fixes, and the delivery people to set up the new water heater. Just in a day’s fun…these videos made it all easier.

  • Autumn

    YES! What happened to Shannyn Sossamon??!?! She was arguably my first girl crush. Mostly because of the underappreciated Josh Hartnett rom-com “40 Days and 40 Nights”.

  • Nico

    Loved this recap! I was so into Alexander Greenwald & Phantom Planet when these came out.

    I also choreographed my high school class’ homecoming parade dance based on that swing dance khakis ad! These ads were obviously very influential on me! Haha!