Working in fashion means that sartorial inspiration can strike at any notice. This could come in the form of subconsciously soaking up the outfits of your fellow passengers on your commute to work before realising you’re replicating them the next time you’re in the office or simply lusting over something you’ve seen on your daily social media scroll. The latter happened to me the other day, when I inadvertently stumbled upon a photo of Cindy Crawford visiting Kaia Gerber on the set of Ryan Murphy’s new ‘80s thriller, The Shards.
Now, I’m not immune to the lure of the iconic off-duty images of Cindy during her ‘90s heyday. There’s something about the effortlessly polished, girl-next-door ease that always pulls me in and wishing for a pair of perfectly taut vintage jeans or an expertly crisp white t-shirt. However, I’d be lying if I said I wasn’t more interested in the personal style of her daughter in all its sleek, slouchily romantic glory. That was until, as I mentioned, coming across this photo of the style muse’s timeless jeans outfit.
(Image credit: Backgrid UK)
The look itself came a few weeks after the supermodel’s 60th birthday, further cementing why I gravitated towards it in the first place, which is that, when it comes to a great outfit, timelessness always wins out over trends. Wearing a pair of bootcut jeans, a satin button-down and a simple leather jacket—a formula she’s been relying on for four decades in a row now—the ensemble proved that investing in classic wardrobe staples that are insusceptible to the passage of time is the best choice one can make.
Indeed, Cindy has been stepping out in similar pieces for years, highlighting that even the upper echelons of fashion are quite strict in sticking to their self-imposed uniform. I might be from a different generation, but there is a lesson to be gleaned in knowing oneself and sticking to the garments that pique my interest.
(Image credit: Getty Images)
Of course, it would be remiss to say that I’m not slightly taken by the polish of her sophisticated blouse and the casual elegance of her outerwear, let alone her trademark brunette bombshell blowout, and I doubt I’m alone in that. So, whether you’re looking to emulate her style philosophy or just her style, scroll on for Cindy Crawford’s over-50s jeans outfit that has this mid-20s talking.
Shop Cindy Crawford’s Bootcut Jeans:
Reformation
Blair High Rise Baby Bootcut Jeans
From Cindy Crawford to CBK, this exact outfit is such an understated dresser’s dream.
MANGO
Fiona Flared Mid-Rise Jeans
The contrast between the icy blue jeans and navy blue sweater is such a luxe way to bring visual tension into your look.
H&M
Bootcut Regular Jeans
These feel like something you’d fish out of a vintage store.
Gap
Dark Blue Low Rise 90s Loose Jeans
Darker indigo jeans are something Crawford has been wearing since she broke through in the ’80s.
CALVIN KLEIN
90s Straight Jeans
A Canadian tuxedo has never looked more chic.
CITIZENS OF HUMANITY
Genova Low-Rise Bootcut Jeans
These crop right at the hips.
AGOLDE
Low-Rise Bootcut Jeans
Cut from slouchy denim for a streamlined, low-slung fit.
RE/DONE
Twisted Mid-Rise Bootcut Jeans
You’ll never want to take these off.









