The Art Of The Gap Ad

And my personal favorites

Aug 27, 2025

I started curating this last a few weeks back before any marketing controversies and potential rebuttals were swirling around in the media. I suppose in light of The Gaps viral and well received Katseye ad, this post is all the more relevant.

I grew up shopping at the Gap and never grew out of it. My mother has always been the classic American shopper, dressing me and my siblings in all the notable legacy brands in American retail. Every year of back to school shopping, Christmas pajamas, and hand me down from one sibling to the next likely had the tag OLD NAVY or GAP on the label inside. She was loyal, so much so that she even got married in a white Gap midi skirt- truly ahead of her time.

As someone with a degree in marketing and a large affinity for American culture Gap isn’t just one of my favorite places to pick up basics, but also one of my favorite companies when it comes to marketing efforts. Similar to Apple’s old advertisements that would play into feel good and relatability, Gap has always had their finger on the pulse when it comes be being relatable, aspirational and fun.

Over the summer I stumbled across the Instagram account Gapplaylists where they post old Gap ads as well hunts down their in store playlists through the years and I quickly started developing a list of favorites. Anyway, lets get into the ads that really do it for me, of course I couldn’t include them all but to name a few;

Just about everybody who has an interest in clothing has seen the multi colored striped knitwear from Gap, maybe you’ve even been lucky enough to get your hands on one. There is something so refreshing about vibrancy in Holiday ads. The traditional dark knits and the occasional creams are trusty for the colder seasons but there is magic in colors year round.

Although two decades old, the styling in this ad feels are current as ever. A skinny scarf, a suede slouchy bag and cropped pant, I know you’ll see this girl on the streets of NYC in fall 2025.

Pop culturally these are two of my favorite people and I will more than happily take them together. Kravitz performs Are You Gonna Go My Way and SJP rocks out. If your curious to watch the entirety of this amazing commercial ( I know you are) you can catch it here!

A denim ad with denim hardly in sight? The glamour is there and its working for me. Also loved the era of the 90’s actress meets pixie cut, the sexy androgyny is chefs kiss.

The golden tones and airbrushed makeup look, it actually doesn’t get better than this to me. I would do anything to be captured in this way and I would do anything to get into the store in the Fall of 1996 to see what exactly is being sold. Beauty sells, I don’t even need to see the clothes!

More of these muted tones, and yes they are working. Looking like an actual barbie doll, maybe a synchronized swimmer. The pose, the attitude, the cut. No wonder Gap has stuck around.

This isn’t selling anything for me but I am still ready to purchase. This sort of feels reminiscent of some sort of computer software manual, but maybe I’m just imagining that.

No piece of clothing is particularly groundbreaking, or interesting in this ad yet the stylized vision of a 90s takes 50s is enough to make you want it!

If there’s a SJP Gap ad, there’s a fan in me. Actual perfection from head to toe and if I could get my hands on every single piece they styled her in, I’d have it.

This is giving high fashion, yet it’s a pair of stretch pants from the Gap. It’s really something. Also need this whole outfit as well. Classics never fail.