The Gap Renaissance Is in Full Swing—3 Fall Looks Our Co-Founder Says You Need

Sponsor Content Created With Gap

When it comes to fashion, no brand evokes more nostalgia for my childhood than Gap. Every time I step into the store, memories swirl of my parents in the '90s: my mom in those oversize Gap overalls and my dad in the iconic logo sweatshirt that I still try to steal to this day. When I was a kid, Gap was the destination for cool wardrobe staples, even before that term was so buzzy. Today, the same remains true, and the brand's new Icons collection of elevated yet approachable fall apparel is proof. The whole Who What Wear team can't get enough of the Gap renaissance, and to prove our commitment, I tapped our co-founder Hillary Kerr to share the pieces she's reaching for this season. Gap's classic, well-made pieces have always inspired her style—she still has a blazer from the '90s in her wardrobe rotation to this day, and there's no doubt that the following three outfits will have the same shelf life. Whether you're looking for new denim, cozy knits, or classic fall cords, the best of the best fall apparel is below. Keep scrolling to shop her looks.

Outfit Formula #1: Striped Knit + Dark Denim


(Image credit: @hillarykerr; Original Illustration by Makena Frederick)

"As a person of very medium height, I'm always on the lookout for pieces that elongate my legs, and these jeans do the trick nicely. They somehow manage the neat trick of being deliciously stretchy but still structured, and the mini bootcut silhouette works perfectly with a sharp heel. And can we talk about how delicious this striped sweater is? It's so good I got it in two colorways!" — Hillary Kerr, co-founder, Who What Wear

Outfit Formula #2: Trucker Jacket + Corduroy Flares


(Image credit: @hillarykerr; Original Illustration by Makena Frederick)

"I'm absolutely wild about these flared cords and plan on wearing them all of fall and for years to come. The richness of the sable-brown color is both luxurious and reminiscent of my favorite '90s shades. I'm also deeply into the fit of these cords; the high waist hits me perfectly, and I love the flare, which makes a statement, but subtly. I would dress this one down by swapping out the office-ready merino wool sweater for a simple white T-shirt, and I'd dress it up by adding my go-to leather jacket." — Kerr

Outfit Formula #3: Button-Down + Faux-Leather Pants


(Image credit: @hillarykerr; Original Illustration by Makena Frederick)

"This is my first foray into the land of leather pants, and I think I quite like it here. I love a classic style with a twist, and these trousers offer just that thanks to their easy-to-style skinny-jean cut. For fall, I think they look great styled with a lightweight denim shirt, and then I'll swap in that cozy striped sweater and a pair of chunky, flat boots when the temperature dips in winter." — Kerr

Natalie Gray Herder
Editor, Branded Content

Natalie Gray Herder is an Editor on the branded content team at Who What Wear. Originally from Los Angeles, Natalie decided to make the move to NYC after graduating from Loyola Marymount University in 2019. She is an avid researcher, reader, and explorer in and out of the office. She is inspired by the street style of her fellow New Yorkers and her laid-back roots in California.