Though our writer thinks maybe it never went away.
I’m about to do that annoying thing every music geek does when they tell you they’ve been listening to a band you just discovered forever, but I’m going to do it about…the Gap. Okay, we all wore Gap in the ’90s and I am certainly not the first (I may actually be the last) to write about the brand’s recent resurgence. I mean, The New Yorker just covered it. But long before Zac Posen stepped in and made all the fashion people take notice, I wrote a story about my secret love affair with the preppy, mass market store.
It was 2018 and I had just worn a white wrap dress that was “a tad Reformation, a tad Marilyn Monroe, not a tad stereotypical Gap” to my wedding rehearsal dinner—yes, I wore Gap at my wedding—and I felt like it was time to let the world know that the Gap was cool. Or more like, you can find cool things at the Gap that won’t look like they are from the Gap, so know one will ever have to know.
Now eight years later, everyone is talking about the Gap—but this time, it might actually be cool.
Even though she hates to admit it, one of my most fashion-y friends, trend forecaster, creative director, and Jenny contributor, Darcy Barber, is now completely on Team Gap. “For years Gap was the retail equivalent of toast—fine, familiar, deeply unmemorable,” she says. “But the sea of samesies has fully shape-shifted into something utterly unexpected: the insider’s fashion darling. Not ironically, not nostalgically, but earnestly cool.”
While Barber does think this new-found appreciation could somewhat lie in the fact that the smell of a Gap store in the ’90s still lives deep in our olfactory memory, she says the Gap’s real “genius right now is that it is not aspirational in an exhausting way—it’s foundational.”
Meaning: They are making clothes we will actually wear. “These aren’t throwaway pieces,” she says. “These are the grown-up, well-cut, I-pay-my-own-health-insurance staples that make a wardrobe work. You wear them because you like yourself now. And maybe you even kinda wanna be comfortable?”
When I wrote my first article, my whole thing was (and still is), that yes, the Gap makes great basics (this tee for the win), but they also do some trendy pieces that feel much more subtle than what you might find at Zara or H&M—and much less likely to be tossed in the donation bin after one or two wears. Basically, you can put them on and still feel like a grown-up.
At the time, the Gap was all about DÔEN knockoffs—they even, somewhat surprisingly, ended up doing a collaboration with the brand. Today, you can still find romantic tops, pointelle tanks, and lace shorts that have that Boho California feel. But you can also find a sweater that might be mistaken for The Row, their version of the leather bomber jacket everyone is wearing at the moment, and the love-or-hate-them barrel jeans.
And finally, the last thing I love about the Gap: There is always a sale. Do not ever pay full price, if you do, it’s guaranteed to be 40% off two days later. And if it sells out, don’t worry, it’s likely that it will be restocked very soon—just like these gingham pants I was sad to see gone in my size, and now, voilà, they have suddenly reappeared. So, without further ado, here are our picks from the Gap for spring (and no, this is not sponsored).
A trench coat? For spring? Groundbreaking. But seriously, everyone needs a trench coat for spring—and Gap makes the quintessential classic—but this cropped version is a little more fun, and a lot less obvious.
Poplin Drop-Waist Maxi Skirt
Like the ’90s, long skirts are back, and I love this one with a dropped waist. If that’s not your thing, this slip skirt is another great option. While I’d go for it in white (despite being very dangerous), it comes in an array of colors and patterns. Pair it with the matching cropped tank, and you instantly have an elevated outfit.
Speaking of matching: One of things the Gap is truly mastering these days—and something I can’t resist—is the matching set. This linen top has a plethora of options it could be paired with for a chic monochromatic look. But really, it would work with most anything. I’m feeling the longer length (not everything has to be cropped!), and maybe even by summer, I will be brave enough to wear it without the removable straps.
One of the easiest things to throw on over any outfit is a denim jacket, but a chore style feels a lot more fresh (and French!) than the classic button-up we’ve all been wearing for the past 20 years. This one is perfect if you like an over-sized look (though the reviews recommend sizing down) and if you want something a little more fitted, this one seems great, too.
VintageSoft Terry Raglan Sweatshirt
Everyone needs a fitted gray crew-neck sweatshirt in their wardrobe. It can be worn, you know, like a sweatshirt, dropping your kids off at school OR take the place of a sweater, dressed up with leather pants or a fun skirt, and some chunky jewelry. If you already have a gray one, the next step is getting one in a fun color like tangerine.
My favorite thing to wear as a beach cover-up lately is an oversized vintage men’s button up. But if you don’t have the time or patience to sift through a thrift store these days, this pink-striped linen shirt (it has other color options, too) has that same retro feel and easy spring break vibe. It would also look great worn with a pair of jean shorts.
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Megan Cahn started her editorial career at Sassy’s less irreverent younger cousin, CosmoGIRL. She went on to work in the women’s lifestyle space at publications such as ELLE, Refinery29, Cup of Jo, and Best Life. She lives in Brooklyn with her husband, cat, and five-year-old daughter, who has adopted her childhood Cabbage Patch Kids collection.
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