Beautiful Virgin Islands

Wednesday, May 13, 2026

Model Behavior: Shop Kaia Gerber and Cindy Crawford’s Street Style Moments

Model Behavior: Shop Kaia Gerber and Cindy Crawford’s Street Style Moments

In honor of Vogue’s latest cover story (in which both Gerber and her mother appear), we’re celebrating both models’ off-duty looks.

They say the apple doesn’t fall far from the tree, and that couldn’t be truer of Kaia Gerber and Cindy Crawford. Yes, the two are both well-spoken, drop-dead gorgeous supermodels, but they also share a knack for looking good off the runway. It might be their Southern California lifestyle that allows each woman to embody a sense of easy-breezy dressing. Which is to say, they don’t overthink things. Why not wear a t-shirt when you look so good doing it? And yes, subtlety printed slip dress really doesn’t require too much accessorizing. As for jeans, they both do denim incredibly well, which is not so surprising, really. The jean gene seems to run in the family-remember when Gerber and her brother Presley were the faces of Calvin Klein?

So in honor of Vogue’s latest cover story (in which both Gerber and her mother appear), we’ve decided to take a look at a few of their street style moments, below.

Blazers, Jeans, and Tees




It’s an uncomplicated outfit formula that requires little to nothing else. Slip a double-breasted jacket over t-shirts (mom prefers black while daughter does white) and wear with a pair of straight-leg jeans. It’s a look that epitomizes model-off-duty.

Midi-Length Slip Dresses




Can you wear a wispy dress with boots? Gerber makes the case in a bias-cut dress from Réalisation. Crawford, meanwhile, makes a case for the flip-flop.

Tailored Suiting




For those moments when they’re (at least expecting and planning) to be on camera, the mother-daughter duo opts for tailored suiting and a black bag. Both look pretty great in their respective suits.

Newsletter

Related Articles

Beautiful Virgin Islands
0:00
0:00
Close
The Great Western Exit: Why Best Citizens Are Fleeing the Rich World [PODCAST]
The New Robber Barons of Intelligence: Are AI Bosses More Powerful Than Rockefeller?
The End of the Old Order [Podcast]
Britain’s Democracy Is Now a Costume
The AI Gold Rush Is Coming for America’s Last Open Spaces [Podcast]
The Pentagon’s AI Squeeze: Eight Tech Giants Get In, Anthropic Gets Shut Out [Podcast]
The War Map: Professor Jiang’s Dark Theory of Iran, Trump, China, Russia, Israel, and the Coming Global Shock [Podcast]
Labour Is No Longer a National Party [Podcast]
AI Isn’t Stealing Your Job. It’s Dismantling It Piece by Piece.
Lawyers vs Engineers: Why China Builds While America Litigates [Podcast]
Churchill’s Glass: The Drunk, the Doctor, and the Myth Britain Refuses to Sober Up From
Apple issues an unusual warning: this is how your iPhone can be hacked without you doing anything
The Met Gala Meets the Age of Billionaire Backlash
Russian Oligarch’s Superyacht Crosses Hormuz via Iran-Controlled Route
Gunfire Disrupts White House Correspondents’ Dinner as Trump Is Evacuated
A Leak, a King, and a Fracturing Alliance
Inside the Gates Foundation Turmoil: Layoffs, Scrutiny, and the Cost of Reputational Risk
UK Biobank Breach Exposes Health Data of 500,000, Listed for Sale on Chinese Platform
KPMG Cuts Around 10% of US Audit Partners After Failed Exit Push
French Police Probe Suspected Weather-Data Tampering After Unusual Polymarket Bets on Paris Temperatures
News Roundup
Microsoft lost 2.5 millions users (French government) to Linux
Privacy Problems in Microsoft Windows OS
News roundup
Péter András Magyar and the Strategic Reset of Hungary
Hungary After the Landslide — A Strategic Reset in Europe
×