For me, scoring new jeans is a closet triumph. But breaking them in? That’s an uphill battle. I’ve learned, albeit the hard way, to wear jeans at least five times before they’re no longer stiff.
Currently, Hailey Bieber and I are both taming under-$100 pairs from Gap before denim season picks up next month. I went with an on-sale straight-leg style, inspired by Fall 2025 runway trends. Bieber, on the other hand, channeled what Marie Claire‘s fashion features editor, Emma Childs, coined a “Low-Slung and Slouchy” silhouette. The supermodel chose Gap’s Low Rise ’90s Loose Jeans, marking her fifth re-wear since August 20.
On August 28, she took the $80 best-sellers out for two spins in the same day. First, she styled them for a Los Angeles errands run with Justin Bieber. They’re available in six colorways, ranging from a light sky-blue wash to black. Bieber chose the Blue Indigo option, which felt right up Louis Vuitton, Khaite, and Nili Lotan’s Fall 2025 alley. The almost-black bottoms were as dark as as they were low-rise, falling a full inch below her navel. Taking cues from their nostalgic name, the hems were somewhere in between straight and wide-leg.
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Hailey Bieber clearly can’t get enough of these $80 jeans.
(Image credit: Backgrid)
Gap
Low Rise ’90s Loose Jeans
Leaning into the ’90s-ness of it all, Bieber paired her jeans with all-black separates, including The Row City Flip-Flops. She’s certainly gotten her money’s worth out of the $890 leather thongs. Since April, Bieber, Kendall Jenner, and Zoë Kravitz have hardly taken them off.
On top, Bieber wore a cropped black tank, further emphasizing the jeans’ dropped waist. For her purse, the Rhode founder selected the Small Park Tote from her The Row-filled closet. Though it retails for $6,100, the Park is one of the trickiest styles to track down. If you’re a fan, you can shop similar leather totes—minus the woven exterior—for a fraction of the price.
The Row
City Flip Flop in Leather
The Row
Brown Medium Woven N/s Tote
The Row
N/s Park Tote Small Bag
A few hours later, Bieber returned to the street style scene. It’s common for A-listers to switch looks if they’re stepping out twice in one day. Bieber, however, stuck with her now-signature Gap jeans.
Next, Bieber ditched her black tank for a white counterpart, layered underneath a leather moto jacket. Her Park Tote was noticeably absent, but the City Flip-Flops held down The Row fort.
Later that night, Hailey was photographed again in the same Gap bottoms.
(Image credit: Backgrid)
Bieber’s denim-clad looks came at the perfect time: I needed some fashion inspiration for Labor Day weekend. Sure, I’m missing her four-figure The Row finds, but I already placed an order for her Gap jeans. Catch me sporting them this weekend and every Saturday after.
Shop Styles Inspired by Hailey Bieber
Gap
Low Rise ’90s Loose Jeans
Gap
Low Rise ’90s Loose Jeans
Gap
Low Rise ’90s Loose Jeans
Gap
Low Rise ’90s Loose Jeans
Gap
Low Rise ’90s Loose Jeans
Gap
Closeknit Jersey Brami
Gap
Closeknit Jersey Brami
Banana Republic
Leather Moto Jacket
Nili Lotan x Tkees
Leather Flip Flop
